Name: 481-72-1|1,8-Dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione|97%
Brand: Ambeed
SKU: A142364
Price: 5.0 USD
Availability: InStock
Rating: 92 (40 reviews)

1
[ 481-72-1 ]
[ 108-24-7 ]
[ 25395-11-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	With pyridine at 50℃; for 24h;	4.1.4 Synthesis of 3-(acetoxymethyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl diacetate (A5) Acetic anhydride (3 mL) was added into a solution of aloe-emodin A1 (1 mmol, 0.27 g) in dry pyridine (10 mL). The mixture was stirred at 50 °C for 24 h, monitored by TLC. After the completion of reaction, the reaction mixture was poured into ice water and yellow solid was separated. Recrystallization of the yellow solid from acetone gave compound A5 as pale yellow needle, yield 76%; mp 143-145 °C; IR νmax cm-1: 3449, 2928, 2097, 2028, 1770, 1736, 1673, 1634, 1612, 1444, 1373, 1332, 1257; 1H NMR (CDCl3): δ = 2.20 (s, 3H, COCH3); 2.47 (s, 6H, 2COCH3); 5.23 (s, 2H, CH2); 7.39 (s, 1H, H-C(4)); 7.41 (d, 1H, J = 8.0 Hz, H-C(7)); 7.78 (dd, 1H, J1 = 8.0 Hz, J2 = 7.9 Hz, H-C(6)); 8.20 (s, 1H, H-C(2)); 8.23 (d, 1H, J = 7.9 Hz, H-C(5)); ESI-MS m/z: 397.09 [M+H]+.
	With sodium acetate

Reference： [1]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[2]Liddell; King; Beal [Journal of the American Pharmaceutical Association (1912), 1942, vol. 31, p. 161,162]

2
[ 481-72-1 ]
[ 98-88-4 ]
[ 69232-86-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In acetone at 60℃; for 24h;	4.1.2 Synthesis of 3-((benzoyloxy)methyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl dibenzoate (A3) Benzoyl chloride (2 mmol, 2 ml), anhydrous K2CO3 (0.5 g) and aloe-emodin (0.5 mmol, 0.135 g) were added into dry acetone (100 ml). The mixture was stirred at 60 °C for 24 h, monitored by TLC. After the completion of reaction, the reaction mixture was poured into ice water and pale yellow solid was separated. Recrystallization of the pale yellow solid from acetone gave compound A3 as pale yellow needle, yield 78%; mp 118-121 °C; IR νmax cm-1: 3434, 3086, 2924, 1733, 1676, 1599, 1449, 1339, 1314, 1276, 1249; 1H NMR (CDCl3): δ = 5.51 (s, 2H, CH2), 7.25 (s, 1H, H-C(4)); 7.29 (d, 2H, H on the ring of benzoyl C(3)), 7.45 (m, 4H, H on the ring of benzoyl C(1, 8)), 7.50 (t, 1H, H on the ring of benzoyl C(3)), 7.56 (d, 1H, J = 8.0 Hz, H-C(2)), 7.61 (dd, 1H, J1 = 8.0 Hz, J2 = 8.0 Hz, H-C(6)), 7.78 (s, 1H, H-C(7)), 7.81 (d, 1H, J = 7.9 Hz, H-C(5)), 8.02 (d, 4H, H on the ring of benzoyl C(1, 8)), 825 (d, 2H, H on the ring of benzoyl C(3)); 831 (d, 2H, H on the ring of benzoyl C(1, 8)); ESI-MS m/z: 583.14 [M+H]+.
	With pyridine

Reference： [1]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[2]Liddell; King; Beal [Journal of the American Pharmaceutical Association (1912), 1942, vol. 31, p. 161,162]

3
[ 6736-63-6 ]
[ 481-72-1 ]
[ 102830-97-7 ]

Yield	Reaction Conditions	Operation in experiment
49%	With 3 A molecular sieve; silver trifluoromethanesulfonate In dichloromethane for 4h; Ambient temperature;

Reference： [1]Abramson; Banning; Nachtman; Roginski; Sardessai; Wormser; Wu; Nagia; Schroeder; Bernardo [Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1709 - 1714]

4
[ 481-72-1 ]
[ 72036-12-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With HBr(aq.) In hydrogen bromide for 3h; Heating;
81.9%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 2h;
72.1%	With phosphorus tribromide In tetrachloromethane for 48h; Reflux;	1.1 Synthesis of bromo aloe emodin 1.38 g of aloe-emodin (5.11 mmol) was dissolved in 250 mL of a three-necked flask with 150 mL of CC14 and 5 mLThe residue was purified by silica gel column chromatography to give an orange solid, 1.23 g, i.e., bromo aloe emodin, and the eluent was dichloromethane / petroleum. The residue was stirred at room temperature for 24 h. Ether = 2: 1 (ν / ν); product characterization data are as follows: Yield is 72.1%

72.1%	With phosphorus tribromide In tetrachloromethane at 65℃; for 48h;	1.1 synthesis of aloe emodin bromide 5.1mmol Aloe-emodin is dissolved into 150mL of CC14; under the room temperature add 5mL of PBr3 (excess), heated at 65 ° C, the reaction is stirred for 48 h under reflux; after the solvent has been removed by rotary evaporation, the residue is purified by silica gel column chromatography (eluent V (CH2C12): V (petroleum ether) = 2: 1) and then obtained an orange solid aloe-emodin; the product characterization data is given as follows:Yield 72.1%.
72.1%	With phosphorus tribromide In chloroform for 24h; Reflux;	1 Example 1: Synthesis of bromo-aloe emodin Aloe-emodin1g (3.7 mmol) was dissolved in 100 mL CHCl3, 0.5 mL (5.3 mmol) PBr3 was added at room temperature, the reaction was stirred under heating and refluxing for 24 h, and the solvent was removed by rotary evaporation under reduced pressure, and purified by silica gel column chromatography with CH2Cl2 to obtain the compound 2 (ie bromoaloe-emodin) orange-yellow solid, yield 72.1%.
71.2%	With carbon tetrabromide; triphenylphosphine In tetrahydrofuran at 20℃; for 6.1h;	Preparation of compound 2 Dissolve triphenylphosphine (4.3g, 16.4mmol) in tetrahydrofuran (40mL),Gradually add carbon tetrabromide (5.4g, 16.4mmol) in batchesAdd to the reaction solution,After the addition, react at room temperature for 10 minutes.Add the modified anthraquinone natural product (810mg, 3mmol) to the reaction solution,After adding, react at room temperature for 6h.TLC monitors the completion of the reaction, stops the reaction, suction filtration, the filter cake is washed with a small amount of tetrahydrofuran, the filtrate is concentrated, and purified by silica gel column chromatography, eluent: petroleum ether-dichloromethane=1:1 (V/V), to obtain a yellow solid 711mg , Yield: 71.2%
	With 1,2-dibromo-1,1,2,2-tetrachloroethane; polymer-bound PPh₃ In dichloromethane at 20℃; for 0.5h;
	In hydrogen bromide	2 EXAMPLE 2 EXAMPLE 2 1,8-Dihydroxy-3-bromomethyl-9,10-anthraquinone (formula 2, in which X is Br) may be prepared as follows. A suspension of aloe-emodin (5 g) in 48% hydrobromic acid is refluxed for 2 hours to afford a precipitate. The precipitate is filtered to afford a crystalline solid which is extracted with CHCl3. The extract is washed with saturated NaCl solution, dried over Na2 SO4, and then evaporated till about 3/5 of its volume, producing a precipitate, which is filtered to give bright orange needles (5.4 g). Recrystallization from CHCl3 gives bright orange-yellow needles having a m.p. of 217°-219° C.
	With hydrogen bromide for 5h; Reflux;	1.1 3- (bromomethyl) anthracene-9,10-dihydroxy-Preparation of 1,8-dione 48% hydrobromic acid then dissolve the Aloe aunt Dean (1 g, 3.7 mmol) in (40 ml) was stirred under reflux for 5 hours. When thin layer chromatography confirmed that the reaction was completed by (TLC), the reaction mixture was cooled to room temperature, the precipitate was then filtered off. The filtered precipitate was washed with water, and recrystallized from acetic acid target compound (0.85 g, 69%) was obtained.
	With phosphorus tribromide In 1,1,2,2-tetrachloroethane at 65℃; for 3h;

Reference： [1]Alexander; Bhatia; Clark III; et al. [Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 24 - 28]
[2]Location in patent: experimental part Cui, Xing-Ri; Takahashi, Kazutoshi; Shimamura, Takeshi; Koyanagi, Jyunichi; Komada, Fusao; Saito, Setsuo [Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 4, p. 497 - 503]
[3]Current Patent Assignee: FUZHOU UNIVERSITY - CN105399640, 2016, A Location in patent: Paragraph 0014
[4]Current Patent Assignee: FUZHOU UNIVERSITY - CN105924364, 2016, A Location in patent: Paragraph 0013; 0015
[5]Current Patent Assignee: FUZHOU UNIVERSITY - CN110981909, 2020, A Location in patent: Paragraph 0010
[6]Current Patent Assignee: INST MED PLANT DEV CAMS - CN112778280, 2021, A Location in patent: Paragraph 0095; 0096
[7]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[8]Current Patent Assignee: UNIVERSITY OF KANSAS - US4215062, 1980, A
[9]Current Patent Assignee: KOREA RESEARCH INSTITUTE OF BIOSCIENCE AND BIOTECHNOLOGY - KR101484086, 2015, B1 Location in patent: Paragraph 0107 - 0109
[10]Li, Ruihong; Li, Wei; You, Yutong; Guo, Xiucai; Peng, Ying; Zheng, Jiang [Chemical Research in Toxicology, 2019, vol. 32, # 6, p. 1281 - 1288]

5
[ 481-72-1 ]
[ 75694-01-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With thionyl chloride In dichloromethane; N,N-dimethyl-formamide for 3h; Heating;
90%	With thionyl chloride In N,N-dimethyl-formamide at 20℃;	41 Example 41. Preparation of intermediate 3-(chloromethyl)-1,8-dihydroxyanthracene-9,10-dione (6) Dissolve aloe-emodin (0.27g, 1.0mmol) in DMF (20mL), stir at room temperature for 12h, add 2mL thionyl chloride dropwise, TLC monitors the completion of the reaction, add 60mL ice water and stir.An orange precipitate was obtained. The sediment is filtered,Washing and drying gave a reddish brown solid (90% yield).
90%	With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 12h;

83%	With thionyl chloride In N,N-dimethyl-formamide at 20℃;	Synthesis of 3-(Chloromethyl)-1,8-dihydroxyanthracene-9,10-dione (25) Compound 24 (0.5 g, 1.9 mmol) was added into a 20 ml vial followed by anhydrous DMF (20 ml). Then, 2 ml of thionyl chloride was slowly added under stirring at room temperature and the reaction was stirred overnight. At the consumption of the starting material, the solvent was removed in vacuo and the mixture was diluted with water and extracted with DCM (5 ml, ×3). The combined organic layer was washed with water (50 ml) and brine (50 ml) successively and dried over anhydrous sodium sulfate. The solvent was removed, and the crude product was purified by silica-gel column chromatography (DCM only). The desired product was isolated as a yellow solid (0.44 g). Yield: 83%. 1H NMR (Chloroform-d) δ 12.10 (s, 1H), 12.04 (s, 1H), 7.90-7.84 (m, 1H), 7.86 (s, 1H), 7.73 (t, J = 8.0 Hz, 1H), 7.40-7.31 (m, 2H), 4.64 (s, 2H). 13C NMR (Chloroform-d) δ 192.6, 181.3, 162.8, 162.6, 147.1, 137.4, 134.0, 133.4, 124.8, 123.7, 120.2, 119.8, 115.7, 115.4, 44.6. HRMS (ESI)m/z: Calculated for C15H10O4Cl [M + H]+ 289.0262; Found 289.0262.
61%	With thionyl chloride In N,N-dimethyl-formamide at 20℃;	1 Experimental Example 1 Preparation of Intermediate VI Add in a 150mL round bottom flask1,8-dihydroxy-3-hydroxymethylhydrazine(2.7 g, 10 mmol) and thionyl chloride(20mL, 275mmol),Using N,N-dimethylformamide (200 mL) as a solvent,Stirring reaction at room temperature,Thin layer chromatography was followed until the end of the reaction.Quenched with ice water,Filtered,washing,After recrystallization and other work-up, compound VI (1.76 g) is obtained.The yield was 61.0%.
61%	With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 8h;	1 Example 1, Preparation of Intermediate VIII Add 1,8-dihydroxy-3-hydroxymethylanthraquinone (2.7g, 10mmol) into a 150mL round bottom flaskAnd thionyl chloride (20mL, 275mmol),Use N,N-dimethylformamide (200mL) as solvent,Add and stir for 8h at room temperature,TLC traces to the end of the reaction.Quench with ice water, filter, wash,Intermediate VIII (1.76g) was obtained by post-treatment such as recrystallization;Yield: 61.0%.
61%	With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 28h; Cooling with ice;
55%	With thionyl chloride; N,N-dimethyl-formamide at 20℃; for 26h;	4.1.15 3-(Chloromethyl)-1,8-dihydroxyanthracene-9,10-dione (C1) 2 ml of thionyl chloride was slowly added into a solution of compound A1 (0.27 g, 1.0 mmol) in anhydrous DMF (20 mL) under stirring at room temperature for 26 h, monitored by TLC. After the completion of reaction, 60 mL of ice water was added under stirring to afford orange precipitate. The orange precipitate was filtered, washed and dried. Recrystallization of the orange precipitate from ethanol gave compound C1 as yellow needle, yield 55%; mp 177-178 °C; IR νmax cm-1: 3426, 3041, 1672, 1627, 1569, 1478, 1454, 1422, 1381, 1276; 1H NMR (CDCl3): δ = 4.62 (s, 2H, CH2), 7.31 (s, 1H, H-C(4)), 7.35 (d, 1H, J = 8.0 Hz, H-C(7)), 7.71 (dd, 1H, J1 = 7.5 Hz, J2 = 8.0 Hz, H-C(6)), 7.85 (s, 1H, H-C(2)), 7.86 (d, 1H, J = 7.5 Hz, H-C(5), 12.04 (s, 1H, HO), 12.07 (s, 1H, HO); ESI-MS m/z: 289.03 [M+H]+.
	Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 6 h / 20 °C 2: thionyl chloride / N,N-dimethyl-formamide / 26 h / 20 °C

Reference： [1]Krohn, Karsten; Baltus, Wolfgang [Liebigs Annalen der Chemie, 1982, # 8, p. 1579 - 1581]
[2]Current Patent Assignee: SICHUAN UNIVERSITY - CN111592479, 2020, A Location in patent: Paragraph 0277-0279
[3]Qiu, Xiang; Pei, Heying; Ni, Hengfan; Su, Zhengying; Li, Yong; Yang, Zhuang; Dou, Caixia; Chen, Lijuan; Wan, Li [Chemical Biology and Drug Design, 2021, vol. 97, # 2, p. 358 - 371]
[4]Agbowuro, Ayodeji A.; Anifowose, Abiodun; Lu, Wen; Tan, Chalet; Tripathi, Ravi; Wang, Binghe; Yang, Xiaoxiao [Medicinal Chemistry Research, 2020, vol. 29, # 7, p. 1199 - 1210]
[5]Current Patent Assignee: SOUTHWEST UNIVERSITY - CN109553579, 2019, A Location in patent: Paragraph 0038; 0039; 0040
[6]Current Patent Assignee: SOUTHWEST UNIVERSITY - CN112209881, 2021, A Location in patent: Paragraph 0044-0046
[7]Ansari, Mohammad Fawad; Ansari, Mohammad Fawad; Battini, Narsaiah; Gan, Lin-Ling; Liang, Xin-Yuan; Sui, Yan-Fei; Zhou, Cheng-He
[8]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[9]Shi, Da-Hua; Huang, Wei; Li, Chao; Liu, Yu-Wei; Wang, Shi-Fan [European Journal of Medicinal Chemistry, 2014, vol. 75, p. 289 - 296]

6
[ 65615-58-9 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium hydroxide In ethanol for 0.166667h; Heating;
94%	With sodium hydroxide for 24h; Ambient temperature;

Reference： [1]Benfaremo, Nicholas; Cava, Michael P. [Journal of Organic Chemistry, 1985, vol. 50, # 1, p. 139 - 141]
[2]Bloomer, James L.; Stagliano, Kenneth W.; Gazzillo, Joseph A. [Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7906 - 7912]

7
[ 72049-23-1 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol at 140 - 150℃; for 6h;

Reference： [1]Alexander, Jose; Bhatia, Ashok V.; Mitscher, Lester A.; Omoto, Shoji; Suzuki, Toshio [Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 20 - 24]

8
[ 481-72-1 ]
[ 77-78-1 ]
[ 50488-95-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In acetone Reflux;	Synthesis of 3-Hydroxymethyl-1,8-dimethoxy-anthracene-9,10-dione (2) To a stirred solution of AE (0.27 g, 1.0 mmol)and potassium carbonate (2.76 g, 20 mmol) in acetone at room temperature, a solution of dimethyl sulfate (2.0 mL, 20 mmol)in acetone (5.0 mL) was added dropwise, and the resulting mixture was heated at reflux. After the completion of the reaction(monitored by TLC), the solvent was removed under reduced pressure, and 5 mL of NaOH solution (2 mol/L) was added.The mixture was extracted with CH2Cl2, dried over MgSO4 and concentrated under vacuum to afford a crude product, whichwas purified with silica flash-chromatography (EA-PE, 1:2) to give a yellow solid compound (85%, mp 224-226°C).
78%	With potassium carbonate In acetone at 60℃; for 12h;	1 Example 1, Preparation of intermediate 3-(hydroxymethyl)-1,8-dimethoxyanthracene-9,10-dione Dissolve aloe-emodin (10.8g, 40mmol) in 300mL acetone,Add dimethyl sulfate (9.5mL, 100mmol), potassium carbonate (22.1g, 160mmol),Reflux at 60°C for 12h. After the reaction, the mixture was cooled to room temperature and filtered.The residue was washed with water and dried in the air to obtain yellow solid compound 2(Yield: 78%).
78%	With potassium carbonate In acetone at 56℃; for 12h;

65%	With potassium carbonate In acetone at 56℃; for 12h;	4.1.1 Synthesis of 3-(hydroxymethyl)-1,8-dimethoxyanthracene-9,10-dione (A2) Aloe-emodin (1 mmol, 0.27 g), dimethyl sulfate (10 mmol, 1 ml) and potassium carbonate (10 mmol, 1.38 g) in 200 ml of dry acetone were refluxed for 12 h at 56 °C till the reaction was accomplished. After the completion of reaction, the yielded mixture was cooled to room temperature and filtered. The filtrate was distilled to afford a yellow solid. Recrystallization of the yellow solid from acetone gave compound C11 as yellow needle, yield 65%; mp 223-225 °C; IR/cm-1: 3129, 2989, 1662, 1591, 1400, 752; 1H NMR (DMSO-d6): δ = 3.91 (s, 6H, 2CH3), 4.64 (d, J = 5.7 Hz, 2H, CH2O), 5.54 (t, J = 5.7 Hz, 1H, OH), 7.21 (1H, s, H-C(2)), 7.30 (1H, d, J = 8.2 Hz, H-C(7)), 7.58 (1H, s, H-C(4)), 7.61 (1H, d, J = 7.5 Hz, H-C(5)), 7.74 (1H, dd, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(6)); ESI-MS m/z: 299.10 [M+H]+
65%	With potassium carbonate In acetone at 56℃; for 12h;	6 Synthesis of 3-(hydroxymethyl)-1,8-dimethoxyanthracene-9,10-dione Aloe-emodin (1 mmol, 0.27 g), dimethyl sulfate (10 mmol, 1 mL) and potassium carbonate (10 mmol, 1.38 g) in 200 mL of dry acetone were refluxed for 12 h at 56 °C till the reaction was accomplished. After the completion of reaction, the yielded mixture was cooled to room temperature and filtered. The filtrate was distilled to afford a yellow solid. Recrystallization of the yellow solid from acetone gave compound B1 as yellow needle, yield 65%; m.p. 223-225 °C; IR/cm-1: 3129, 2989, 1662, 1591, 1400, 752; 1H NMR (d6-DMSO): δ = 3.91 (s, 6H, 2CH3), 4.64 (d, J = 5.7 Hz, 2H, CH2O), 5.54 (t, J = 5.7 Hz, 1H, OH), 7.21 (1H, s, H-C(2)), 7.30 (1H, d, J = 8.2 Hz, H-C(7)), 7.58 (1H, s, H-C(4)), 7.61 (1H, d, J = 7.5 Hz, H-C(5)), 7.74 (1H, dd, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(6)); HRMS (ESI): calcd for [M + H]+ (C17H15O5) m/z 299.0919, found 299.0924.
61.6%	With potassium carbonate In acetone Reflux;
55%	With potassium carbonate In 1,4-dioxane; acetone Heating; Time : 12 h;

Reference： [1]Chen, Chao; Cao, Tingting; Li, Yong; Hu, Yuegao; Yang, Hongjun; Yin, Shufan [Chemistry of Natural Compounds, 2020, vol. 56, # 1, p. 30 - 33][Khim. Prir. Soedin., 2020, vol. 56, # 1, p. 31 - 34,4]
[2]Current Patent Assignee: SICHUAN UNIVERSITY - CN111592479, 2020, A Location in patent: Paragraph 0155-0157
[3]Qiu, Xiang; Pei, Heying; Ni, Hengfan; Su, Zhengying; Li, Yong; Yang, Zhuang; Dou, Caixia; Chen, Lijuan; Wan, Li [Chemical Biology and Drug Design, 2021, vol. 97, # 2, p. 358 - 371]
[4]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[5]Shi, Da-Hua; Huang, Wei; Li, Chao; Liu, Yu-Wei; Wang, Shi-Fan [European Journal of Medicinal Chemistry, 2014, vol. 75, p. 289 - 296]
[6]Location in patent: experimental part Cui, Xing-Ri; Takahashi, Kazutoshi; Shimamura, Takeshi; Koyanagi, Jyunichi; Komada, Fusao; Saito, Setsuo [Chemical and Pharmaceutical Bulletin, 2008, vol. 56, # 4, p. 497 - 503]
[7]Alexander, Jose; Bhatia, Ashok V.; Mitscher, Lester A.; Omoto, Shoji; Suzuki, Toshio [Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 20 - 24]

Yield	Reaction Conditions	Operation in experiment
	With sodium peroxide; water at 80 - 85℃;
	With potassium hydroxide; air man ansaeuert die Fluessigkeit mit H₂SO₄ und der Loesung das Aloeemodin mit Benzol entzieht; die Benzolloesung schuettelt man mit waessr.Ammoniak und faellt aus der ammoniakalischen Loesung mit Salzsaeure das Aloeemodin aus;
	With hydrogenchloride bei Siedetemperatur,dann bei Zimmertemperatur;

	With sodium peroxide; water bei Siedetemperatur,dann bei Zimmertemperatur;
	With caro's acid
	With water; iron(III) chloride at 125℃;
	With hydrogenchloride; ethanol

Yield	Reaction Conditions	Operation in experiment
	With sodium peroxide; water at 80 - 85℃;
	With hydrogenchloride bei Siedetemperatur,dann bei Zimmertemperatur;
	With sodium peroxide; water bei Siedetemperatur,dann bei Zimmertemperatur;

11
Aloe-emodin 1-O-beta-D-glucopyranoside [ No CAS ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With acetate buffer; β-glucosidase In water at 37℃; for 16h;
	Enzymatic reaction;

Reference： [1]Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Park, Ji-Young; Harima, Shoichi; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 1, p. 41 - 50]
[2]Kageura, Tadashi; Matsuda, Hisashi; Morikawa, Toshio; Toguchida, Iwao; Harima, Shoichi; Oda, Mamiko; Yoshikawa, Masayuki [Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1887 - 1893]

12
[ 75-30-9 ]
[ 481-72-1 ]
[ 355022-16-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With caesium carbonate In acetone for 96h; Heating;

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

13
[ 481-74-3 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: Chrysophanol With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 6h; Heating; Stage #2: With water; calcium carbonate In 1,4-dioxane at 120℃; for 7h;
	Multi-step reaction with 2 steps 1: NBS; (PhCO₂)2 / CCl₄ / 6 h / Heating 2: 756 mg / H₂O; CaCO₃ / dioxane / 7 h / 120 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]
[2]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

14
[ 439290-04-7 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium <i>tert</i>-butylate; water In tetrahydrofuran; diethyl ether; dichloromethane at 20℃; for 12h;

Reference： [1]Uno, Hidemitsu; Masumoto, Akane; Honda, Erina; Nagamachi, Yumi; Yamaoka, Youtarou; Ono, Noboru [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2001, # 23, p. 3189 - 3197]

15
[ 75-30-9 ]
[ 481-72-1 ]
[ 355022-16-1 ]
3-isopropoxymethyl-1,8-diisopropoxyanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 82% 2: 7%	With caesium carbonate In acetone for 12h; Heating;

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

16
[ 72036-12-5 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
756 mg	With water; calcium carbonate In 1,4-dioxane at 120℃; for 7h;
	Multi-step reaction with 3 steps 1: 780 mg / H₂ / 10percent Pd/C / methanol / 1 h / 3000.3 Torr 2: NBS; (PhCO₂)2 / CCl₄ / 6 h / Heating 3: 756 mg / H₂O; CaCO₃ / dioxane / 7 h / 120 °C
	Multi-step reaction with 2 steps 1: acetic acid / 0.5 h / Heating 2: 100 percent / 2percent KOH / ethanol / 0.17 h / Heating

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[3]Benfaremo, Nicholas; Cava, Michael P. [Journal of Organic Chemistry, 1985, vol. 50, # 1, p. 139 - 141]

17
[ 481-72-1 ]
[ 64-19-7 ]
[ 481-74-3 ]
[ 65615-58-9 ]

Yield	Reaction Conditions	Operation in experiment
1: 25% 2: 52%	With tin(ll) chloride In hydrogenchloride at 120℃; for 1h;

Reference： [1]Kuhnert, Nikolai; Molod, Hoshiar Y. [Tetrahedron Letters, 2005, vol. 46, # 44, p. 7571 - 7573]

18
[ 1415-73-2 ]
[ 481-72-1 ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7571 - 7573

19
[ 481-72-1 ]
[ 355022-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 78 percent / pyridine / 5 h / 70 °C
	Multi-step reaction with 2 steps 1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2: 94 percent / pyridine / 3 h / 50 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

20
[ 481-72-1 ]
1-bromo-2-hydroxymethyl-4,5-diisopropoxyanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 32 percent / NaOAc; I₂; Br₂ / CCl₄; CHCl₃ / 3 h / Heating
	Multi-step reaction with 2 steps 1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2: 32 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 2 h / Heating

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

21
[ 481-72-1 ]
[ 355022-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 78 percent / pyridine / 5 h / 70 °C 3: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C
	Multi-step reaction with 4 steps 1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2: 94 percent / pyridine / 3 h / 50 °C 3: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4: 91 percent / KOH / methanol / 2 h / 70 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

22
[ 481-72-1 ]
[ 355022-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 78 percent / pyridine / 5 h / 70 °C 3: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C
	Multi-step reaction with 5 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

23
[ 481-72-1 ]
[ 355022-22-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 78 percent / pyridine / 5 h / 70 °C 3: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating
	Multi-step reaction with 3 steps 1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2: 94 percent / pyridine / 3 h / 50 °C 3: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

24
[ 481-72-1 ]
[ 355022-29-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C
	Multi-step reaction with 7 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

25
[ 481-72-1 ]
[ 355022-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2: 78 percent / pyridine / 5 h / 70 °C 3: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C
	Multi-step reaction with 6 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]
[2]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

26
[ 481-72-1 ]
(P)-4,5-dihydroxy-1-(2',4'-dimethoxy-6'0hydroxyphenyl)-2-methylanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 12 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr 12.1: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

27
[ 481-72-1 ]
13-bromo-1,3-dimethoxy-8,10-diisopropoxy-6H-anthraquinone[2,1-c]benzopyran-9,14-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 54 percent / H₂; Et₃N / 10percent Pd/C / methanol / 0.25 h / 2625.26 Torr

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

28
[ 481-72-1 ]
13-bromo-1,3-dimethoxy-8,10-diisopropoxy-9-hydroxy-6H-anthra[2,1-c]benzopyran-6,14-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / Et₃N; formic acid / 10percent Pd/C / dimethylformamide / 2.25 h / 50 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

29
[ 481-72-1 ]
(Sa)-13-bromo-1,3-dimethoxy-8,10-diisopropoxy-6H-anthraquinone[2,1-c]benzopyran-9,14-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

30
[ 481-72-1 ]
(R_a)-knipholone anthrone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 15 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr 12.1: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 13.1: 82 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 14.1: 41 percent / AlBr₃ / chlorobenzene / 20 - 80 °C 15.1: 64 percent / SnCl₂; HCl / acetic acid / 2 h / Heating

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

31
[ 481-72-1 ]
(Sa)-6'-O-methylknipholone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 13 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr 12.1: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 13.1: 82 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

32
[ 481-72-1 ]
(Ra)-4'-O-demethylknipholone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr 12.1: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 13.1: 82 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 14.1: 62 percent / AlBr₃ / chlorobenzene / 1.5 h / 80 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

33
[ 481-72-1 ]
(R_a)-knipholone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 14 steps 1.1: 82 percent / Cs₂CO₃ / acetone / 12 h / Heating 2.1: 78 percent / pyridine / 5 h / 70 °C 3.1: 89 percent / NaOAc; Br₂ / CCl₄; CHCl₃ / 3 h / Heating 4.1: 91 percent / aqueous NaOH / methanol / 2 h / 70 °C 5.1: 93 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C 6.1: 97 percent / amidosulfuric acid; NaClO₂; NaOAc / dioxane; H₂O; acetic acid / 1.5 h / 20 °C 7.1: 90 percent / 4-dimethylaminopyridine; dicyclohexylcarbodiimide / dimethylformamide; CH₂Cl₂ / 0.58 h / 0 - 20 °C 8.1: Pd(OAc)2; PPh₃; NaOAc / 2 h / 60 °C / 0.01 Torr 8.2: 36 percent / N,N-dimethyl-acetamide / 6 h / 120 - 130 °C 9.1: 65 percent / BH₃-THF complex; (S)-1-Me-3,3-diPh-tetrahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran / 1 h / 0 °C 10.1: polymer-bound PPh₃; (CBrCl₂)2 / CH₂Cl₂ / 0.17 h / 20 °C 11.1: 48 percent / H₂; NaOAc / 10percent Pd/C / 2 h / 2625.26 Torr 12.1: 89 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 13.1: 82 percent / TiCl₄ / CH₂Cl₂ / 2 h / -20 - 20 °C 14.1: 41 percent / AlBr₃ / chlorobenzene / 20 - 80 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk; Kraus, Juergen; Muehlbacher, Joerg; Peters, Karl; Peters, Eva-Maria; Brun, Reto; Bezabih, Merhatibeb; Abegaz, Berhanu M. [Journal of Organic Chemistry, 2002, vol. 67, # 16, p. 5595 - 5610]

34
[ 481-72-1 ]
1-(2-hydroxy-4,6-dimethoxy-phenyl)-4,5-diisopropoxy-2-methyl-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C 8.1: (S)-3,3-di-Ph-1-Me-perhydropyrrolo[1,2-c]oxazaborol-BH₃ / tetrahydrofuran / 1 h / 0 °C 9.1: (CBrCl₂)2; polymer-bound PPh₃ / CH₂Cl₂ / 0.17 h / 20 °C 9.2: 48 percent / H₂ / Pd/C / methanol

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

35
[ 481-72-1 ]
6'-O-methylknipholone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C 8.1: (S)-3,3-di-Ph-1-Me-perhydropyrrolo[1,2-c]oxazaborol-BH₃ / tetrahydrofuran / 1 h / 0 °C 9.1: (CBrCl₂)2; polymer-bound PPh₃ / CH₂Cl₂ / 0.17 h / 20 °C 9.2: 48 percent / H₂ / Pd/C / methanol 10.1: TiCl₄ / CH₂Cl₂ / -20 - 20 °C 10.2: TiCl₄ / -20 - 20 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

36
[ 481-72-1 ]
(+)-M-knipholone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 11 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C 8.1: (S)-3,3-di-Ph-1-Me-perhydropyrrolo[1,2-c]oxazaborol-BH₃ / tetrahydrofuran / 1 h / 0 °C 9.1: (CBrCl₂)2; polymer-bound PPh₃ / CH₂Cl₂ / 0.17 h / 20 °C 9.2: 48 percent / H₂ / Pd/C / methanol 10.1: TiCl₄ / CH₂Cl₂ / -20 - 20 °C 10.2: TiCl₄ / -20 - 20 °C 11.1: 41 percent / AlBr₃ / chlorobenzene / 2 h / 80 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

37
[ 481-72-1 ]
8-bromo-1-(2-hydroxy-4,6-dimethoxy-phenyl)-2-hydroxymethyl-4,5-diisopropoxy-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C 8.1: (S)-3,3-di-Ph-1-Me-perhydropyrrolo[1,2-c]oxazaborol-BH₃ / tetrahydrofuran / 1 h / 0 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

38
[ 481-72-1 ]
8-bromo-1-(2-hydroxy-4,6-dimethoxy-phenyl)-2-hydroxymethyl-4,5-diisopropoxy-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: 72 percent / Cs₂CO₃ / acetone / 96 h / Heating 2.1: 94 percent / pyridine / 3 h / 50 °C 3.1: 89 percent / Br₂; NaOAc / CHCl₃; CCl₄ / 3 h / 70 °C 4.1: 91 percent / KOH / methanol / 2 h / 70 °C 5.1: MnO₂ / CH₂Cl₂ / 6 h / 20 °C 5.2: NaClO₂; amidosulfuric acid; NaOAc / dioxane; H₂O; acetic acid / 20 °C 6.1: 90 percent / DCC; DMAP / CH₂Cl₂; dimethylformamide / 1 h / 0 - 20 °C 7.1: 68 percent / palladium(II) acetate; triphenylphosphine; sodium pivalate / N,N-dimethyl-acetamide / 4.5 h / 130 °C 8.1: (R)-3,3-di-Ph-1-Me-perhydropyrrolo[1,2-c]oxazaborol-BH₃ / tetrahydrofuran / 1 h / 0 °C

Reference： [1]Bringmann, Gerhard; Menche, Dirk [Angewandte Chemie - International Edition, 2001, vol. 40, # 9, p. 1687 - 1690]

39
[ 481-72-1 ]
[ 14963-97-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: H₃BO₃ / 6 h / Heating 2: Ag₂O / dimethylformamide 3: KMnO₄, KOH / H₂O / Heating

Reference： [1]Alexander, Jose; Bhatia, Ashok V.; Mitscher, Lester A.; Omoto, Shoji; Suzuki, Toshio [Journal of Organic Chemistry, 1980, vol. 45, # 1, p. 20 - 24]

Yield	Reaction Conditions	Operation in experiment
		100 kg of crude humid diacerein (equivalent to 62 kg of dry diacerein), are dissolved at a maximum pH between 7.0-7.2 in a mixture of 375.8 kg of water and 441.2 kg of acetone; 16.33 kg of triethylamine dissolved in 186.2 kg of acetone at a temperature of 23-25C for 6-8 hours are required. when diacerein has dissolved completely, 10 extractions are performed with 100 liters of toluene, using 10 liters in every extraction. After that, the water phase is adjusted to a pH of about 2.8 with 80% phosphoric acid and a 91-92.5% weight/weight yield, 8 ppm of aloe-emodin, 23 ppm of chromium, 99.24% purity and a 98.55% concentration is obtained.
		In the same procedure of example 1, after the dissolution, 10 extractions with 100 liters of ethyl acetate, using 10 liters in every extraction are performed; after crystallization at a pH of about 2.2, using 80% phosphoric acid, a 88-90% weight/weight yield, 10 ppm of aloe-emodin, 25 ppm of chromium, a purity of 99.16% and a concentration of 98.96% are obtained.
		In the same procedure of example 1, after the dissolution, 10 extractions with 100 liters of toluene, using 10 liters in every extraction are performed; after crystallization at a pH of about 2.8, using 10% sulphuric acid, a 90-93% weight/weight yield, 7 ppm of aloe-emodin, 20 ppm of chromium, a purity of 99.31% and a concentration of 99.44% are obtained.

		In the same procedure of example 1, after the dissolution, 10 extractions with 100 liters of isobutyl acetate, using 10 liters in every extraction are performed; after crystallization at a pH of about 2.5, using 10% sulphuric acid, a 92-93% weight/weight yield, 9 ppm of aloe-emodin, 23 ppm of chromium, a purity of 99.24% and a concentration of 98.55% are obtained.
		In the same procedure of example 1, after the dissolution, 10 extractions with 100 liters of xylene, using 10 liters in every extraction are performed; after crystallization at a pH of about 2.7, using 10% sulphuric acid, a 91-93% weight/weight yield, 7 ppm of aloe-emodin, 21 ppm of chromium, a purity of 99.31% and a concentration of 99.44% are obtained.
		In the same procedure of example 1, after the dissolution, 10 extractions with 100 liters of xylene, using 10 liters in every extraction are performed; after crystallization at a pH of about 3.0, using 30% phosphoric acid, a 90-92% weight/weight yield, 8 ppm of aloe-emodin, 24 ppm of chromium, a purity of 98.76% and a concentration of 98.99% are obtained.

41
[ 481-72-1 ]
[ 154658-30-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: aloe emodin With TEMPOL; anhydrous sodium carbonate In dichloromethane at 37℃; for 0.5h; Stage #2: With trichloroisocyanuric acid In dichloromethane	4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (2) A mixture of aloe emodin (540 mg, 2.00 mmol), 4-hydroxy-TEMPO (18 mg, 0.10 mmol) andanhydroussodium carbonate (180 mg, 1.70 mmol) was stirred in dichloromethane (70 mL) at 37 °C for 30 min, urea trichloroisocyanate (540 mg, 2.32 mmol) was added to continue reacting. The reaction process was detected by TLC (dichloromethane/petroleum ether = 5/1, v/v, Rf= 0.84). When the reaction was completed, the filtrate was washed with water (350 mL), the organic layer was dried by anhydrous sodium sulfate and removed under reduced pressure to afford yellow solid (380 mg, 1.41 mmol) with the yield of70%; mp: 205-207 °C.
70%	Stage #1: aloe emodin With TEMPOL; anhydrous sodium carbonate In dichloromethane at 37℃; for 0.5h; Stage #2: With trichloroisocyanuric acid In dichloromethane	4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (2) A mixture of aloe emodin (540 mg, 2.00 mmol), 4-hydroxy-TEMPO (18 mg, 0.10 mmol) andanhydroussodium carbonate (180 mg, 1.70 mmol) was stirred in dichloromethane (70 mL) at 37 °C for 30 min, urea trichloroisocyanate (540 mg, 2.32 mmol) was added to continue reacting. The reaction process was detected by TLC (dichloromethane/petroleum ether = 5/1, v/v, Rf= 0.84). When the reaction was completed, the filtrate was washed with water (350 mL), the organic layer was dried by anhydrous sodium sulfate and removed under reduced pressure to afford yellow solid (380 mg, 1.41 mmol) with the yield of70%; mp: 205-207 °C.
60%	With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;	4.1.6 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 0.33 g (1.50 mmol) of pyridinium chlorochromate (PCC) was added in 200 ml of dichloromethane containing 0.27 g of compound A1 (1.0 mmol). The yielded mixture was stirred at room temperature 6 h till the reaction was accomplished. After the completion of reaction, the reaction mixture was washed with water in the separatory funnel. The dichloromethane layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solutions were dried for eight hours over anhydrous sodium sulfate and then the dichloromethane was distilled off to afford a yellow solid. Recrystallization of the yellow solid from ethanol gave compound B1 as yellow needle, yield 60%; mp 208-210 °C; IR νmax cm-1: 3131, 1703, 1672, 1626, 1401, 1267; 1H NMR (DMSO-d6): δ = 7.44 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.78 (s, 1H, H-C(1)), 7.84 (s, 1H, H-C(3)), 7.87 (dd, 1H, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(7)), 8.15 (d, 1H, J = 7.5 Hz, H-C(8)), 10.13 (s, 1H, CHO), 11.94 (s, 2H, OH); ESI-MS m/z: 269.04 [M+H]+.

60%	With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;	1 Synthesis of 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde 0.33 g (1.50 mmol) of pyridinium chlorochromate (PCC) was added in 200 mL of dichloromethane containing 0.27 g of compound 1 (1.0 mmol). The yielded mixture was stirred at room temperature 6 h until the reaction was accomplished. After the completion of reaction, the reaction mixture was washed with water in the separatory funnel. The dichloromethane layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined dichloromethane solutions were dried for 8 h over anhydrous sodium sulfate and then the dichloromethane was distilled off to afford a yellow solid. Recrystallization of the yellow solid from ethanol gave compound A1 as yellow needle, yield 60%; m.p. 208-210 °C; IR νmax cm-1: 3131, 1703, 1672, 1626, 1401, 1267; 1H NMR (d6-DMSO): δ = 7.44 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.78 (s, 1H, H-C(1)), 7.84(s, 1H, H-C(3)), 7.87 (dd, 1H, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(7)), 8.15 (d, 1H, J = 7.5 Hz, H-C(8)), 10.13 (s, 1H, CHO), 11.94 (s, 2H, OH); HRMS (ESI): calcd for [M + H]+ (C15H9O5) m/z 269.0450, found 269.0453.
60.7%	With pyridinium chlorochromate In propan-2-one for 24h; Reflux;	The general procedures for the synthesis of 4,5-disubstituted-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (5-8) Aloe-emodin or 4, 5-alkoxy substituted aloe-emodin in acetone was added to a 250 mL flask and stirred. Silica supported PCC (20 g) was added to the above solution. The mixture was stirred under reflux for about 24 h, the reaction process was monitored by TLC (EtOAc/PE (60-90oC) = 1:3). When no starting material could be detected, the reaction mixture was filtered and washed with acetone. Solvent of the combined organic phases was removed under reduced pressure to get crude product, which was purified by column chromatography with ethyl acetate in petroleum ether.
56%	With pyridinium chlorochromate In dichloromethane at 20℃; for 6h;
56%	With pyridinium chlorochromate In dichloromethane at 20℃;	General procedure for synthesis of 2 To the stirring solution of 1.62 g of aloe emodin (1) dissolved in 200 ml of dichloromethane, about 2.90 g of pyridiniumchlorochromate (PCC) was added and kept for 6 h at room temperature. The process of reaction was monitored using TLC until the reaction was completed. After the completion of reaction, the reaction mixture was workup with water: DCM in the separating funnel and the organic layer was separated and further extracted twice with DCM. The combined DCM layer was dried with anhydrous sodium sulfate for 8 h and the DCM was distilled off to get the yellow solid. To obtain the pure compound (2), the yellow solid was recrystallized with methanol which afford pure compound (2) as yellow needle.NMR data of compound 2 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (2) : Yield 56%; mp 220-224°C; IR (KBr) νmax: 3131, 1703, 1672, 1626,1401, 1267 cm-1; 1H NMR (400 MHz, DMSO-d6): δ 11.95 (2H, s), 10.13 (1H, s), 8.14 (1H, d, J = 1.5 Hz), 7.88-7.82 (2H, m), 7.79- 7.75 (1H, m), 7.43 (1H, dd, J = 1.1, 8.3 Hz) ; 13C NMR (101 MHz, DMSO-d6) : δ 192.21, 191.35, 180.98, 161.36, 161.36, 141.39, 137.57, 134.29, 133.21, 124.59, 124.21, 119.58, 119.39, 118.02, 116.27 ppm ; HRMS-ESI (m/z) : (M+H)+ calculated for C15H9O5 ; 269.0450, found 269.0457.
56%	With pyridinium chlorochromate In dichloromethane at 20℃;	General procedure for synthesis of 2 To the stirring solution of 1.62 g of aloe emodin (1) dissolved in 200 ml of dichloromethane, about 2.90 g of pyridiniumchlorochromate (PCC) was added and kept for 6 h at room temperature. The process of reaction was monitored using TLC until the reaction was completed. After the completion of reaction, the reaction mixture was workup with water: DCM in the separating funnel and the organic layer was separated and further extracted twice with DCM. The combined DCM layer was dried with anhydrous sodium sulfate for 8 h and the DCM was distilled off to get the yellow solid. To obtain the pure compound (2), the yellow solid was recrystallized with methanol which afford pure compound (2) as yellow needle.NMR data of compound 2 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde (2) : Yield 56%; mp 220-224°C; IR (KBr) νmax: 3131, 1703, 1672, 1626,1401, 1267 cm-1; 1H NMR (400 MHz, DMSO-d6): δ 11.95 (2H, s), 10.13 (1H, s), 8.14 (1H, d, J = 1.5 Hz), 7.88-7.82 (2H, m), 7.79- 7.75 (1H, m), 7.43 (1H, dd, J = 1.1, 8.3 Hz) ; 13C NMR (101 MHz, DMSO-d6) : δ 192.21, 191.35, 180.98, 161.36, 161.36, 141.39, 137.57, 134.29, 133.21, 124.59, 124.21, 119.58, 119.39, 118.02, 116.27 ppm ; HRMS-ESI (m/z) : (M+H)+ calculated for C15H9O5 ; 269.0450, found 269.0457.
	With triethylamine In dimethyl sulfoxide	6.1 1 1 9,10-Dihydro-4,5-dihydroxy-9,10-dioxoanthracene-2-aldehyde To aloe-emodin (5.0 g) in dry dimethyl sulphoxide (55 ml) and triethylamine (77 ml) was added a solution/suspension of sulphur trioxide-pyridine complex (29.4 g) in dry dimethyl sulphoxide (100 ml), dropwise with stirring, over 15 minutes. The addition was slightly exothermic and gave a dark brown solution, which was stirred at room temperature for 2-3 hours, then poured onto dilute hydrochloric acid (1000 ml, 0.5M), stirred for 15 minutes, then left to stand for 15 minutes. The suspension was filtered (slow), washed with water (400 ml) and pulled dry to leave a brown solid. Dried at 50° C. in a vacuum oven, m.p. 198°-200° C.
	Stage #1: aloe emodin With 1,4-diaza-bicyclo[2.2.2]octane In 1,4-dioxane at 20℃; for 0.0833333h; Autoclave; Stage #2: With oxygen In 1,4-dioxane at 90℃; for 8h; Autoclave;	1 Example 1 :Process of preparation of 4,5-Dihydroxy-9,10-dioxo-9,10-dihydro-anthracene-2- carbaldehyde from 1 ,8-Dihydroxy-3-hydroxymethyl-anthraquinone through VO(acac)2- DABCO/ 02 oxidation in 1 ,4 dioxane as solventA par autoclave reactor was charged with 200 ml of 1 ,4 Dioxane to that aloe-emodin (85% purity) (3 g) , VO (acac)2 (0.150 g), DABCO (0.200 g) were added and stirred at room temperature for 15 min. Reactor was purged with oxygen gas for 5 min and then 1 bar oxygen pressure was maintained in reactor. The resulting mixture was stirred at 90 °C for 8 h. Reaction was monitored by TLC (1 : 1 , hexane/ethyl acetate). After complete disappearing of starting material (normally after 8hr), reaction mixture was cooled to RT and filtered to remove insoluble material. Filtrate was then poured in 1 L of ice cool water to obtain the product. After filtering and washing with water (200 ml), the collected brown solid was dried at 45° C. in vacuo. Isolated yield: 2 g (79%); Melting point: 202 - 205 °C (Literature melting point 200 °C; USP. 5,480,873); Compound I: 1H NMR (200MHZ, DMSO4 d6): δ 7.38-8.09 (m, Ar), 10.10(s, Ar-CHO), 1 1.98-1 1.95 (m, Ar-OH); IR Spectra (cm'1): 1699, 1673, 1630, 1265.Powder X-ray diffraction:
	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 30℃; for 4h;	4.1 1. Preparation of intermediate formula II Dimethyl sulfoxide (0.65 Kg) was added to the reactor.IBX (84.0g, 0.3mol),Aloe emodin (27.0g, 0.1mol) is stirred,Warm up to 30 ° C,Stir for 4 hours,Take a small amount of the reaction solution for HPLC detection.Aloe-emodin retention is 2.3%,Cool down to 25 ° C,Put 0.65L of water at a constant rate,Warming up to 35 ° C,Stir for 3.5 hours.The reaction solution is filtered,The filter cake was washed once with ethanol (0.35Kg),The filter cake was blast dried at 60 ° C for 10 hours.50.8 g of crude product (yellow) was obtained.The next step was directly carried out without purification.
181 g	With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In 1-methyl-pyrrolidin-2-one at 70℃; for 2h;	1; 2 Example one Add 2kg of N-methylpyrrolidone into the reaction flask,200g aloe-emodin, heated to 70, added 230g IBX,Then it was stirred and incubated for 2h; after the reaction, the temperature was lowered to room temperature,After stirring for 1h, filter with suction, rinse the filter cake with 150g ethanol and drain it.Vacuum drying at 80°C for 12 hours to obtain 181 g of rhubarb aldehyde;

Reference： [1]Deng, Zhao; Sun, Hang; Bheemanaboina, Rammohan R. Yadav; Luo, Yan; Zhou, Cheng-He [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 64]
[2]Deng, Zhao; Sun, Hang; Bheemanaboina, Rammohan R. Yadav; Luo, Yan; Zhou, Cheng-He [Bioorganic and Medicinal Chemistry Letters, 2022, vol. 64]
[3]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[4]Shi, Da-Hua; Huang, Wei; Li, Chao; Liu, Yu-Wei; Wang, Shi-Fan [European Journal of Medicinal Chemistry, 2014, vol. 75, p. 289 - 296]
[5]Liu, Jinbing; Wu, Fengyan; Chen, Changhong [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5142 - 5146]
[6]Bathula, Surendar Reddy; Bathula, Surendar Reddy; Dutta, Hashnu; Kumar, Guddeti Dileep; Siva, Bandi; Suresh Babu, K.; Vadlamudi, Sravanthi
[7]Ashwini, K.; Dileep Kumar, G.; Ramalingam, V.; Sai Balaji, A.; Siva, Bandi; Suresh Babu, K.; Vinod Kumar, J. [Natural Product Research, 2021]
[8]Ashwini, K.; Dileep Kumar, G.; Ramalingam, V.; Sai Balaji, A.; Siva, Bandi; Suresh Babu, K.; Vinod Kumar, J. [Natural Product Research, 2021]
[9]Current Patent Assignee: SHERWIN-WILLIAMS CO - US5480873, 1996, A
[10]Current Patent Assignee: LUPIN LIMITED - WO2011/30350, 2011, A1 Location in patent: Page/Page column 16-17
[11]Current Patent Assignee: ANHUI UNIVERSITY OF CHINESE MEDICINE; HEFEI YUANZHI PHARMACEUTICAL R D - CN108218701, 2018, A Location in patent: Paragraph 0032-0034; 0043-0045; 0054-0056; 0065; 0066; 0067
[12]Current Patent Assignee: JIANGSU KAIDIEN MEDICINE TECHNOLOGY CO LTD - CN111423325, 2020, A Location in patent: Paragraph 0023; 0024-0027

42
[ 481-72-1 ]
[ 478-43-3 ]

Yield	Reaction Conditions	Operation in experiment
93%	With oxygen at 120℃; for 14h; Green chemistry;
85%	With sulfuric acid; sodium nitrite at 120℃; for 3h;	3 Example 3; Oxidizing medium was prepared by dissolving sodium nitrite (255 g) in sulphuric acid (1.2 I). The oxidizing medium was heated to 1200C and then aloe-emodin (100 g) was added slowly thereto. After completion of the oxidation reaction (3 hours), the reaction mixture was poured into distilled water (7.2 I) at 2°C to precipitate rhein, and rhein is filtered and dried. Rhein having a degree of purity of 90 - 95 % was obtained in a yield of more than 85 %.
62%	With water; pyridinium chlorochromate In N,N-dimethyl-formamide at 20℃; for 24h;	4.1.12 4,5-Dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid (B7) A mixture of compound A1 (1 mmol, 0.27 g), PCC (2 mmol, 0.45 g), DMF (100 ml) and 2 mL of water were stirred at room temperature for 24 h, monitored by TLC. After the completion of reaction, 100 mL of ice water was added under stirring to afford orange precipitate. The orange precipitate was filtered, washed and dried. Recrystallization of the orange precipitate from ethanol gave compound B7 as brown acicular crystals, yield 62%; mp 310-313 °C; IR νmax cm-1: 3432, 3059, 2930, 1695, 1628, 1270, 1192, 757; 1H NMR (DMSO-d6): δ = 7.58 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.85 (s, 1H, H-C(1)), 7.97 (dd, 1H, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(7)), 8.01 (s, 1H, H-C(3)), 8.45 (d, 1H, J = 7.5 Hz, H-C(8)), 11.87 (s, 1H, HO-C(1)), 11.94 (s, 1H, HO-C(8)), 13.90 (s, 1H, COOH); ESI-MS m/z: 285.04 [M+H]+.

62%	With pyridinium chlorochromate In water; N,N-dimethyl-formamide at 20℃; for 24h;	4 Synthesis of 4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracene-2-carboxylic acid A mixture of compound 1 (1 mmol, 0.27 g), PCC (2 mmol, 0.45 g), DMF (100 ml) and 2 mL of water were stirred at room temperature for 24 h, monitored by TLC. After the completion of reaction, 100 mL of ice water was added under stirring to afford orange precipitate. The orange precipitate was filtered, washed and dried. Recrystallization of the orange precipitate from ethanol gave compound A4 as brown acicular crystals, yield 62%; m.p. 310-313 °C; IR νmax cm-1: 3432, 3059, 2930, 1695, 1628, 1270, 1192, 757; 1H NMR (d6-DMSO): δ = 7.58 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.85 (s, 1H, H-C(1)), 7.97 (dd, 1H, J1 = 8.2 Hz, J2 = 7.5 Hz, H-C(7)), 8.01 (s, 1H, H-C(3)), 8.45 (d, 1H, J = 7.5 Hz, H-C(8)), 11.87 (s, 1H, HO-C(1)), 11.94 (s, 1H, HO-C(8)), 13.90 (s, 1H, COOH); HRMS (ESI): calcd for [M + H]+ (C15H9O6) m/z 285.0399, found 285.0403.
	Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With dihydrogen peroxide; potassium hydroxide In 1,2-dimethoxyethane; water at 60 - 65℃; Stage #2: With hydrogenchloride In 1,2-dimethoxyethane; water at 55 - 60℃;	2; 3 Example 2:Into a round bottom flask equipped with a mechanical stirrer and two addition funnels were poured, 40Og of KOH 25% (w/w) and 264g of DME (dimethoxyethane). The mixture was heated to 60 ° C. 4Og aloe-emodin (87%) (Laboratoire Medidom, Switzerland) was added, whereby a deep red solution was formed.Potassium hydroxide 50 % (317g) and hydrogen peroxide 50% (317g, 264 ml) were added simultaneously over 4 hours maintaining the temperature between 63 0C - 65 0C. The reaction was followed by HPLC. When the reaction was complete, hydrochloric acid 37% (380 ml) was added over 1.5 - 2 hours until pH 2.0, maintaining the temperature between 55 0C - 60 0C, whereby a yellow / orange solid was formed. The suspension was cooled to 35 0C - 40 0C, and then filtered and washed with water (28Og).33 g of crude rhein was obtained as an orange solid after drying at 70 0C, with a purity of 92%, yield 83%. The rhein thus obtained had aloe-emodin content <0.25% determined by HPLC.Example 3: Purification of rheinRhein obtained according to Example 2 was purified by crystallization using N,N-dimethylacetamide (DMA) (8 parts). Crude rhein was dissolved at 80 0C - 100 0C and then cooled at 15 0C - 20 0C. The product was refluxed in acetone (5 - 10 parts) to minimize the DMA content. The purified rhein had a purity of 98-100%, and the overall yield was higher than 75%
	Multi-step reaction with 2 steps 1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 4 h / 30 °C 2: sodium dihydrogenphosphate; sodium chlorite / dimethyl sulfoxide; water / 4.5 h / 5 - 25 °C

Reference： [1]Liu, Kai-Jian; Jiang, Si; Lu, Ling-Hui; Tang, Ling-Li; Tang, Shan-Shan; Tang, Hai-Shan; Tang, Zilong; He, Wei-Min; Xu, Xinhua [Green Chemistry, 2018, vol. 20, # 13, p. 3038 - 3043]
[2]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2006/51400, 2006, A1 Location in patent: Page/Page column 18
[3]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]
[4]Shi, Da-Hua; Huang, Wei; Li, Chao; Liu, Yu-Wei; Wang, Shi-Fan [European Journal of Medicinal Chemistry, 2014, vol. 75, p. 289 - 296]
[5]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2009/106908, 2009, A1 Location in patent: Page/Page column 12-13
[6]Current Patent Assignee: ANHUI UNIVERSITY OF CHINESE MEDICINE; HEFEI YUANZHI PHARMACEUTICAL R D - CN108218701, 2018, A

43
[ 452311-56-7 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: aloin With hydrogenchloride In water at 20 - 80℃; for 1.41667h; Stage #2: With oxygen; copper(l) chloride In water at 90℃; for 7h;	1 (I) 1L of HCI 3M was poured into a reaction flask and 7Og of aloin 30 (Laboratoire Medidom, Switzerland) (31% of aloin) was added over 5 minutes at room temperature (20-25 0C) with vigorous stirring. The mixture was stirred for 20 minutes and then was heated for one hour at 80 0C. 3.5 g copper (I) chloride was added and a gas diffuser was introduced into the solution. Oxygen gas was introduced at a flow rate of 30 L/h. The mixture was heated at 90 0C for 7 hours with continuous oxygen gas flow and stirring. A dark brown solid was formed.The oxygen gas flow was stopped and the gas diffuser was removed. The resulting suspension was cooled at room temperature overnight. The solid product was filtered and washed with 25 - 30 ml of HCI 3M (the mother liqueurs were retained). The dark brown solid product residue was washed with water (200 - 300 ml). 33.6g of brown solid product residue was obtained, containing 30.0% of Aloe- emodin. 72% yield.The mother liqueurs were used in four successive operations:(2) The mother liqueurs of the 1st oxidation were poured into the flask and 7Og aloin 30 (31% aloin) added as in (I) above. The oxidation was carried out as in (I). 37.9 g of brown solid was obtained, containing 27.0% of aloe-emodin. 73% yield.(3) The mother liqueurs of the 2nd oxidation were poured into the flask and 7Og aloin 30 (31% aloin) added as in (I) above. The oxidation was carried out as in (I).39.0 g of brown solid was obtained, containing 25.3% of aloe-emodin. 70.4% yield.(4) The mother liqueurs of the 3rd oxidation were poured into the flask and 7Og aloin 30 (31% aloin) added as in (I) above. The oxidation was carried out as in (I). 44.3 g of brown solid was obtained, containing 21.0% of aloe-emodin. 66.4% yield.(5) The mother liqueurs of the 4th oxidation were poured into the flask and 7Og aloin 30 (31% aloin) added as in (I) above. The oxidation was carried out as in (I). 40.0 g of brown solid was obtained, containing 21.4% of aloe-emodin. 61.1% yield.Extraction (Soxhlet type) The extractor body was prepared and the pooled solid residues (194g) were added. Toluene (140Og) was added into the flask and the system was refluxed for 16-20 hours. An orange solid was formed. The mixture was cooled at room temperature and the solid filtered and washed with toluene (100g).55.3g of aloe-emodin was obtained as an orange solid, yield 92%, aloe-emodin purity 80%.
75%	With oxygen; nitric acid In ethylene glycol at 120℃; for 6.33333h;	1 Example 1; Crude Aloin (72 g containing 39 % pure aloin) was dissolved in ethylene glycol (250 ml) . The solution was poured in a one-liter reactor and warmed at 1200C under nitrogen atmosphere. When the temperature of 120°C was reached, HNO3(7.58 g) diluted in ethylene glycol (50 ml) was added during 20 minutes. At this time, oxygen gas was introduced at a flow rate of 4 L/min by means of a sparger into the reactor. Samples were withdrawn every hour from reactor and analyzed by HPLC to determine the completion of the reaction. After 6 hours, the reaction was completed. Under these conditions, the conversion rate from aloin to aloe- emodin was 61 %.Isolation of aloe-emodin was then carried out by successively pouring the reaction mixture into water, extracting aloe-emodin with toluene or dichloromethane, evaporating toluene or dichloromethane, drying aloe-emodin (purity: 50%), precipitating aloe-emodin in ethanol, filtering aloe-emodin and drying aloe-emodin to obtain aloe-emodin 95 - 98 % pure. The yield was in a range of 75% - 95%.
	With oxygen; nitric acid In ethylene glycol at 120℃; for 0.333333 - 6.33333h;	The heated aloin-containing solution used in this study has been prepared by dissolving 72 g crude aloin containing 39 % pure aloin in 250 ml ethylene glycol, pouring the solution into a one-liter reactor, warming it to 12O0C in a nitrogen atmosphere and adding over 20 minutes 7.58 g HNO3 diluted in 50 ml ethylene glycol .Oxygen gas at various flow rates was introduced into said heated aloin- containing solution and samples were withdrawn every hour from the reaction mixture and analyzed by HPLC.The results are summarized in Table 1 below.; From Table 1 , it can be seen that in the above specific conditions, the maximum yield of oxidation of aloin into aloe-emodin occurs after 5 - 6 hours if oxygen is introduced at a flow rate ranging from 2 to 4 [L/min].

	With oxygen; nitric acid In ethylene glycol at 105℃; for 5.25h;	2 Example 2; Under nitrogen atmosphere, crude Aloin (3.24Kg, containing 36% pure aloin) was dissolved in ethylene glycol (13.5 I). Under continuous agitation 17Og of nitric acid (dissolved in ethylene glycol) were added over 5 minutes. The solution warmed to a temperature of 1050C. At this time nitrogen was washed out by the introduction of oxygen flow for 10 minutes. The reactor was then pressurized by the introduction of oxygen up to a pressure of 1.5 bars absolute pressure. The oxygen pressure was maintained at 1.5 bars absolute pressure for 5 hours. The reactor was then depressurized to ambient pressure and cooled to room temperature. Under these conditions, the conversion rate from aloin to aloe- emodin was 80%.Isolation of aloe-emodin was then carried out. The reaction mixture containing aloe-emodin in suspension was passed through a stainless steel filter press under pressure (8 bars absolute for 1 hour). The filter cake was then washed with half volume (7 I) of ethylene glycol under pressure (8 bars absolute for 7-8 hours), followed by purified water (8 bars absolute pressure for 2 hours), glycine buffer (0.1 M at pH 10) for 20 min at 8 bars absolute pressure, and purified water (10 minutes at 8 bars absolute pressure). The filter cake was then partially dried by blowing with nitrogen at 11 bars absolute pressure.Methylene chloride was then passed through the filter cake in a continuous manner to extract aloe-emodin. The methylene chloride solution was added to an aqueous solution buffered with glycine 0.1 M at pH 10, and the liquids separated using a liquid-liquid centrifuge. Buffer solution was continuously recirculated until saturation, after which new buffer was constantly added and saturated buffer constantly washed out to maintain a steady concentration in the reaction vessel. The methylene chloride solution, still containing aloe-emodin, was then added to an aqueous solution containing NaOH 1M and the liquids separated using a liquid-liquid centrifuge. NaOH solution containing aloe-emodin was continuously recirculated until saturation, after saturation new NaOH 1M solution was constantly added and NaOH solution saturated with aloe-emodin EPO constantly washed out and collected elsewhere to maintain a steady concentration in the reaction vessel.The solution of aloe-emodin in NaOH was then precipitated by the addition of hydrochloric acid. Fine orange needles of aloe-emodin were precipitated on lowering the pH to below 1. The precipitate was then filtered, washed with purified water and dried with hot nitrogen. The aloe-emodin obtained had a purity of 99%.
8.6 mg	With iron(III) chloride In water for 0.5h; Reflux;	Preparation of AE: 30.0 mg of AL was suspended in 50 mL aqueousFeCl3 (15%) and boiled under refllux for 30 min. After cooling, the solutionwas extracted with ethyl acetate (3 × 20 mL), and the organiclayers were combined and evaporated to dryness, yielding 11.3 mg AE.The substance was further purified by sublimation at 210 C to give 8.6mg of AE crystals.
8.6 mg	With iron(III) chloride In water for 0.5h; Reflux;	Preparation of AE: 30.0 mg of AL was suspended in 50 mL aqueousFeCl3 (15%) and boiled under refllux for 30 min. After cooling, the solutionwas extracted with ethyl acetate (3 × 20 mL), and the organiclayers were combined and evaporated to dryness, yielding 11.3 mg AE.The substance was further purified by sublimation at 210 C to give 8.6mg of AE crystals.

Reference： [1]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2009/106910, 2009, A1 Location in patent: Page/Page column 7-8
[2]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2006/51400, 2006, A1 Location in patent: Page/Page column 16
[3]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2006/51400, 2006, A1 Location in patent: Page/Page column 9
[4]Current Patent Assignee: LABORATORIE MEDIDOM SA - WO2006/51400, 2006, A1 Location in patent: Page/Page column 17-18
[5]Adomako-Bonsu, Amma G.; Maser, Edmund; Thiele, Solveig; Westermann, Magdalena; Çiçek, Serhat Sezai; Martin, Hans-Jörg [Chemico-Biological Interactions, 2022, vol. 354]
[6]Adomako-Bonsu, Amma G.; Maser, Edmund; Thiele, Solveig; Westermann, Magdalena; Çiçek, Serhat Sezai; Martin, Hans-Jörg [Chemico-Biological Interactions, 2022, vol. 354]

44
[ 481-72-1 ]
[ 100-44-7 ]
[ 1204745-87-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 50 - 80℃;	1 Example 1 Preparation of 1,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone (Dibenzyl Aloe-emodin); 483 g (3.5 moles) of potassium carbonate, 16 g (0.1 moles) of potassium iodide and 16 g (0.05 moles) of tetrabutylammonium bromide are added to a solution of 270 g (1 mole) of 1,8-dihydroxy-3-(hydroxymethyl)anthraquinone (aloe-emodin) in 3500 ml of DMF at 60° C.; the reaction mixture is heated at 80° C. for 1 h. It is cooled to 50° C. and 443 g (3.5 moles) of benzyl chloride are added dropwise in approximately one hour. At the end of the dripping, the reaction mixture is brought back to 80° C. and left at that temperature under stirring for 45-60 minutes. It is then cooled to 50° C. and 200 ml of methyl alcohol are added. It is cooled to 20-25° C. and the inorganic salts are removed by filtering. The organic solvent is distilled at 60-70° C. at reduced pressure and the residue is dissolved in 3200 ml of tetrahydrofuran at 60° C. Maintaining the temperature at 50-60° C., the organic phase is washed twice with 1200 ml of 2.5 molar aqueous sodium hydroxide and once with 1000 ml of a saturated solution of sodium chloride in water. The organic phase is concentrated at reduced pressure at 60° C. and the residue is recovered with 2700 ml of ethyl acetate. The suspension thus obtained is concentrated to approximately of the initial volume by distillation of the solvent at reduced pressure. It is gradually cooled to 0-4° C. and kept at that temperature for 1 hour. The solid is filtered and washed with ethyl acetate (100 ml×2). The damp product is dried at 45° C. at reduced pressure for 12-14 hours, providing 334 g (yield 74%) of dibenzyl aloe-emodin having a purity of 98% (HPLC).melting point: 170-171° C.IR cm-1: 1655, 1612, 1232
	Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With potassium carbonate In N,N-dimethyl-formamide at 60 - 80℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 50 - 80℃; for 1.75 - 2h;	1 Example 1; Preparation of l,8-dibenzyloxy-3-(hydroxymethyl)anthraquinone (dibenzyl aloe-emodin); 483 g (3.5 moles) of potassium carbonate, 16 g (0.1 moles) of potassium iodide and 16 g (0.05 moles) of tetrabutylammonium bromide are added to a solution of 270 g (1 mole) of l,8-dihydroxy-3-(hydroxymethyl)anthraquinone (aloe-emodin) in 3500 ml of DMF at 600C; the reaction mixture is heated at 800C for Ih. It is cooled to 500C and 443 g (3.5 moles) of benzyl chloride are added dropwise in approximately one hour. At the end of the dripping, the reaction mixture is brought back to 800C and left at that temperature under stirring for 45-60 minutes. It is then cooled to 500C and 200 ml of methyl alcohol are added. It is cooled to 20-250C and the inorganic salts are removed by filtering. The organic solvent is distilled at 60-700C at reduced pressure and the residue is dissolved in 3200 ml of tetrahydrofuran at 600C. Maintaining the temperature at 50-600C, the organic phase is washed twice with 1200 ml of 2.5 molar aqueous sodium hydroxide and once with 1000 ml of a saturated solution of sodium chloride in water. The organic phase is concentrated at reduced pressure at 600C and the residue is recovered with 2700 ml of ethyl acetate. The suspension thus obtained is concentrated to approximately 1/3 of the initial volume by distillation of the solvent at reduced pressure. It is gradually cooled to 0-40C and kept at that temperature for 1 hour. The solid is filtered and washed with ethyl acetate (100 ml x 2). The damp product is dried at 45°C at reduced pressure for 12-14 hours, providing 334 g (yield 74%) of dibenzyl aloe-emodin having a purity of 98% (HPLC). melting point: 170-1710C IR Cm-1I lOSS5 IOn, 1232

Reference： [1]Current Patent Assignee: P&R SPA - US2011/15269, 2011, A1 Location in patent: Page/Page column 2-3
[2]Current Patent Assignee: P&R SPA - WO2009/90483, 2009, A1 Location in patent: Page/Page column 7-8

45
[ 481-72-1 ]
[ 179913-39-4 ]
[ 1309862-14-3 ]
[ 1309862-16-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 30% 2: 11%	Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione; 1,4-di-O-acetyl-3-azido-2,3,6-trideoxy-L-arabino-hexopyranose In tetrahydrofuran at 20℃; for 0.333333h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 0℃; for 40h; Inert atmosphere; Stage #3: With triethylamine In tetrahydrofuran Inert atmosphere;
50 % de	In tetrahydrofuran at 0℃; Molecular sieve; Inert atmosphere;	4 AEGs 13a and 14a: Acosamine glycosyl donor D-l (295.0 mg, 1.15 mmol) and AE (283.4 mg, 1.05 mmol) in dry THF (6.0 ml) were added flame dried molecular sieves (4 A, 400 mg) and stirred under argon atmosphere at ambient temperature for 20 min. The reaction mixture was then cooled to 0°C, added trimethylsilyl trifluoromethanesulfonate (60 /L, 0.33mmol). Reaction progress was monitored by TLC (70% petroleum ether, 30% ethyl acetate) and indicated the formation of an anomeric mixture of products (a-anomer 13a Rf=0.71, (β-anomer 14a Rf=0.57). Upon completion (40h at 0°C) the reaction was quenched by trimethylamine (60 L) and the crude was filtered through a small plug of celite. The products were isolated by reverse-phase HPLC using a Phenomenex Luna axia 5 μτΛ C-18 (250 mm x 21.20 mm) column at a flow rate of 20.0 mL/min. The HPLC solvents were A: H20 (0.1% TFA) and B: ACN (0.1% TFA). The elution gradient was 80%B for 2 min followed by 80-100%B over 20 min and product elution was monitored at 256 nm by a UV detector. The product retention times were 9.4 minutes for the (a-anomer 13a and 8.8 minutes for the β-anomer 14a. Fractions containing the pure product were concentrated under reduced pressure to yield a-anomer 13 a (162.4mg, 0.35mmol), β-anomer 14a (66.3mg, 0.14mmol) and a mixture of both anomers (229.9mg, 0.49mmol). The total isolated yield of the reaction was 43% with an α:β ratio of 1 :3 as indicated by HPLC. NMR (500 MHz, CDC13) for AEG 13a δ: 12.01(s, IH, OH), 1 1.99(s, IH, OH) 7.77(d, J=7.5 Hz, IH, H-5'), 7.67(s, IH, H-4), 7.62(t, J=7.8 Hz, IH, H-6), 7.22(m, 2H, H-2, H-7'), 4.93(bd, J=3.2 Hz, IH, H-1), 4.68(d, J=13.6 Hz, IH, H-15'), 4.64(dd, J/=J2=9.8 Hz, IH, H-4), 4.48(d, J=13.7 Hz, IH, H-15'), 3.87(ddd, Ji=4.9, J2=9.9 J3=12.3 Hz, IH, H-3), 3.75(dq, Ji=6.3, J2=9.6 Ηζ,ΙΗ, H-5), 2.22(bdd, J.=4.9, J2=13.3 Hz, IH, H-2eq), 2.06(s, 3H, COCH3), 1.74(dd, J,=3.5, J2=12.9 Hz, IH, H-2ax), 1.1 l(d, J=6.3 Hz, 3H, H-6). 13C NMR (125.7 MHz, CDC13) for AEG 13a δ: 192.1 (C-9), 181.1(C-10'), 169.6 (COCH3), 162.3, 162.1, 147.6(C-3), 136.8(C-6'), 133.2, 133.0, 124.3, 121.7, 1 19.6, 117.9, 1 15.2, 1 14.5, 95.7 (C-l), 74.8, 67.3, 65.9, 57.0, 34.5(C-2), 20.6(COCHj), 16.9(C-6). Positive HRESIMS, m/z calcd 490.1226 for C23H2iN308Na, found 490.1231 [M+Na]+.'HNMR (500 MHz, CDC13) for AEG 14a δ: 11.94(s, IH, OH), 1 1.93(s, IH, OH) 7.72(d, J=7.4 Hz, IH, H-5'), 7.64(s, IH, H-4'), 7.59(t, J=7.9 Hz, IH, H-6'), 7.20(m, 2H, H-2', H-7'), 4.88(d, J=13.7 Hz, IH, H-15'), 4.63(dd, J.= J2=9.6 Hz, IH, H-4), 4.58(d, J=13.7 Hz, IH, H-15'), 4.56(dd, Ji =1.8, J2=9.7 Hz, IH, H-1), 3.48(ddd, J,=5.0, J2=9.8, J3=12.8 Hz, IH, H-3), 3.40(dq, J,=6.2, J2=9.5 Hz, IH, H-5), 2.27(ddd, Ji=1.4, J2=4.8, J3=12.9 Hz, IH, H-2eq), 2.06(s, 3H, OCH3), 1.72(ddd, J,= J2=9.7, J3=12.7 Hz, IH, H-2ax), 1.18(d, J,=6.2 Hz, 3H, H-6). 13C NMR (100.6 MHz, CDC13) for AEG 14a δ: 193.3(C-9'), 182.3(C-10'), 170.7 (COCH3), 163.5, 163.2, 148.9(C-3'), 137.9(C-6'), 134.3, 134.2, 125.4, 122.9, 120.8, 119.1, 1 16.5, 115.7, 99.5(C-1), 75.6, 71.7, 69.9, 60.4, 36.8(C-2), 21.6(COCHj), 18.2(C-6). Positive HRESIMS, m/z calcd 490.1226 for C23H21N308Na, found 490.1224 [M+Na]+.

Reference： [1]Breiner-Goldstein, Elinor; Evron, Zoharia; Frenkel, Michael; Cohen, Keren; Meiron, Keren Nir; Peer, Dan; Roichman, Yael; Flescher, Eliezer; Fridman, Micha [ACS Medicinal Chemistry Letters, 2011, vol. 2, # 7, p. 528 - 531]
[2]Current Patent Assignee: TEL AVIV UNIVERSITY - WO2011/89602, 2011, A2 Location in patent: Page/Page column 45-46

46
[ 481-72-1 ]
phenyl-4-O-benzoyl-3-deoxy-3-azido-2-deoxy-thio-β-L-xylopyranose [ No CAS ]
C₂₇H₂₁N₃O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃; for 16h; Inert atmosphere; Molecular sieve;	3 Compounds 1 la and 1 lb: Compound lOf, (150 mg, 422 μηιο) with Aloe emodin (137mg, 506 μιηο), and 2,6-di-tert-butyl-4-methyl pyridine (346 mg, 1.67 mmol) were dissolved in dry dichloromethane (5 mL), under argon, and stirred for 40 min with freshly flame dried molecular sieves (200 mg). Silver hexafluorophosphate (533mg, 2.54mmol) was then added and the reaction was stirred at ambient temperature for 16h. The reaction was monitored by TLC (90% acetone, 10% methanol) product Rf=0.21). Upon termination, the mixture was washed through a celite plug, concentrated and loaded on a silica-gel column. The crude was eluted with 90% acetone, 10% methanol and the products were obtain as a mixture of anomers 1 la and 1 lb (80 mg, 156 μϖιο, 37%).

Reference： [1]Current Patent Assignee: TEL AVIV UNIVERSITY - WO2011/89602, 2011, A2 Location in patent: Page/Page column 42

47
Acetic acid (2S,3R,4R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester [ No CAS ]
[ 481-72-1 ]
[ 1309862-18-7 ]
[ 1309862-20-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 21% 2: 34%	Stage #1: Acetic acid (2S,3R,4R)-6-acetoxy-4-azido-2-methyl-tetrahydro-pyran-3-yl ester; 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In tetrahydrofuran at 20℃; for 0.333333h; Molecular sieve; Inert atmosphere; Stage #2: With trimethylsilyl trifluoromethanesulfonate In tetrahydrofuran at 0℃; for 18h; Inert atmosphere; Stage #3: With triethylamine In tetrahydrofuran Inert atmosphere;
	In tetrahydrofuran at 0℃; Molecular sieve; Inert atmosphere;	4 AEGs 15a and 16a: Ristosamine glycosyl donor D-2 (295.0 mg, 1.15 mmol) and AE (283.4 mg, 1.05 mmol) in dry THF (6.0 ml) were added flame dried molecular sieves (4 A, 400 mg) and stirred under argon atmosphere at ambient temperature for 20 min. The reaction mixture was then cooled to 0°C, added trimethylsilyl trifluoromethanesulfonate (60 L, 0.33mmol). Reaction progress was monitored by TLC (70% petroleum ether, 30% ethyl acetate) and indicated the formation of an anomeric mixture of products (a-anomer 15a Rf=0.51, β-anomer 16a Rf=0.69). Upon completion (18h at 0°C) the reaction was quenched by trimethylamine (60 / L) and the crude was filtered through a small plug of celite. The products were isolated by reverse-phase HPLC using a Phenomenex Luna axia 5 μτα C-18 (250 mm x 21.20 mm) column at a flow rate of 20.0 mL/min. The HPLC solvents were A: H20 (0.1% TFA) and B: ACN (0.1% TFA). The elution gradient was 80%B for 2 min followed by 80-100%B over 20 min and product elution was monitored at 256 nm by a UV detector. The product retention times were 8.1 minutes for the a-anomer 15a and 9.4 minutes for the β-anomer 16a. Fractions containing the pure product were concentrated under reduced pressure to yield the pure cc- anomer 15a (113.4mg, 0.24mmol), the pure β-anomer 16a (182.7mg, 0.39mmol) and a mixture of both anomers (373. lmg, 0.80mmol). The total isolated yield of the reaction was 69 % with an α:β ratio of 1 :1 as indicated HPLC. NMR (500 MHz, CDC13) for AEG 15a δ: 12.02(s, IH, OH), 12.01(s, IH, OH) 7.78(d, J=7.4 Hz, IH, H-5'), 7.74(s, IH, H-4'), 7.62(t, J=8.0 Hz, IH, H-6'), 7.32(s, IH, H-2'), 7.24(d, J=8.4 Hz, IH, H-7'), 4.85(d, J=4.0 Hz, IH, H-1) , 4.77(d, J=14.0 Hz, IH, H-15'), 4.62(dd, J.=3.5, J2=9.6 Hz, IH, H-4), 4.53(d, J=14.0 Hz,IH, H-15'), 4.17(dq, J,=6.3, J2=9.5, IH, H-5), 4.12(ddd, J,= J2= J3=3.5 Hz, IH, H-3), 2.20(bdd, Ji=3.0, J2=14.9 Hz, IH, H-2eq), 2.07(s, 3H, OCH3), 2.05(ddd, J,= J2=4.2, J3=14.7 Hz, IH, H-2ax), 1.1 l(d, J=6.3 Hz, 3H, H-6). 13C NMR (100.6 MHz, CDC13) for AEG 15a δ: 193.4(C-9'), 182.4(C-10'), 170.9 (COCH3), 163.6, 163.3, 149.5(C-3'), 137.9(C-6'), 134.4 (C- i r, C-14'), 125.4, 122.9, 120.8, 119.2, 1 16.6, 1 15.7, 95.9(C-1), 74.5, 68.7, 63.0, 56.3, 30.4(C-2) , 21.5(COCH5), 18.0(C-6). Positive HRESIMS, m/z calcd 490.1226 for C23H2iN308Na, found 490.1226 [M+Na]+.'H NMR (500 MHz, CDC13) for AEG 16a δ: 12.01(s, IH, OH),I I .99(s, 1Η, OH) 7.77(d, J=7.5 Hz, IH, H-5'), 7.70(s, IH, H-4'), 7.63(t, J=8.0 Hz, IH, H-6') 7.23(d, J=7.9 Hz, IH, H-7'), 7.19(s, IH, H-2'), 4.89(d, J-13.6 Hz, IH, H-15'), 4.77(dd, J,=2.0, J2=8.9 Hz, IH, H-1), 4.64(dd, Ji=3.4, J2=9.2 Hz, IH, H-4), 4.58(d, J=13.6 Hz, IH, H-15'), 4.15(ddd, J J2= J3=3.5 Hz, IH, H-3), 3.93(dq, Ji=6.3, J2=9.2 Hz, IH, H-5), 2.08(ddd, J,=2.2, J2=4.0, J3=12.0 Hz, IH, H-2eq), 2.07(s, 3H, OCH3), 1.87(ddd, J,=3.4, J2=9.0, J3=12.4 Hz, IH, H-2ax), 1.19(d, J=6.4 Hz, 3H, H-6) 13C NMR (125.7 MHz, CDC13) for AEG 16a δ: 192.2(C- 9'), 181.2(C-10'), 169.6 (COCH3), 162.3, 162.0, 148.0(C-3'), 136.7(C-6'), 133.1(C-1 1', C-14'), 124.2, 121.8, 1 19.6, 1 18.0, 115.4, 114.5, 96.7(C-1), 73.8, 68.7, 67.8, 57.1 , 34.8(C-2), 20.2(COCH3), 17.3(C-6). Positive HRESIMS, m/z calcd 490.1226 for C23H2iN308Na, found 490.1225 [M+Na]+.

Reference： [1]Breiner-Goldstein, Elinor; Evron, Zoharia; Frenkel, Michael; Cohen, Keren; Meiron, Keren Nir; Peer, Dan; Roichman, Yael; Flescher, Eliezer; Fridman, Micha [ACS Medicinal Chemistry Letters, 2011, vol. 2, # 7, p. 528 - 531]
[2]Current Patent Assignee: TEL AVIV UNIVERSITY - WO2011/89602, 2011, A2 Location in patent: Page/Page column 46-48

48
[ 481-72-1 ]
[ 98-59-9 ]
[ 1425440-98-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In acetone at 60℃; for 6h;	4.1.5 Synthesis of 3-(hydroxymethyl)-9,10-dioxo-9,10-dihydroanthracene-1,8-diyl bis(4-methylbenzenesulfonate) (A6) Tosyl chloride (2 mmol, 0.38 g), anhydrous K2CO3 (0.5 g) and aloe-emodin A1 (1 mmol, 0.27 g) were added into dry acetone (15 ml). The mixture was stirred at 60 °C for 6 h, monitored by TLC. After the completion of reaction, the reaction mixture was poured into ice water and pale yellow solid was separated. Recrystallization of the pale yellow solid from acetone gave compound A6 as pale yellow granular crystals, yield 70%; mp 206-208 °C; IR νmax cm-1: 3482, 3071, 2924, 2363, 1925, 1683, 1597, 1493, 1448, 1365, 1319, 1250; 1H NMR (DMSO-d6): δ = 2.39 (s, 6H, 2CH3); 4.66 (s, 2H, CH2); 5.67 (s, 1H, OH); 7.42 (d, 1H, J = 8.0 Hz, H-C(7)), 7.43 (s, 1H, H-C(4)), 7.70 (d, 1H, J = 8.0 Hz, H-C(2)), 7.57 (d, 4H, J = 8.0 Hz, H on the ring of tosyl C(3, 5)), 7.88 (d, 4H, J = 8.0 Hz, H on the ring of tosyl C(2, 6)), 8.07 (dd, 1H, J1 = 8.0 Hz, J2 = 8.0 Hz, H-C(6)), 8.13 (d, 1H, J = 8.0 Hz, H-C(5)); ESI-MS m/z: 579.08 [M+H]+.

Reference： [1]Shi, Da-Hua; Huang, Wei; Li, Chao; Wang, Ling-Ting; Wang, Shi-Fan [Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 5, p. 1064 - 1073]

49
[ 481-72-1 ]
[ 65-85-0 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: benzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

50
[ 107-93-7 ]
[ 481-72-1 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-but-2-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-but-2-enoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

51
[ 481-72-1 ]
[ 501-52-0 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3-phenylpropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-Phenylpropionic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

52
[ 481-72-1 ]
[ 621-82-9 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl cinnamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Cinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

53
[ 481-72-1 ]
[ 100-09-4 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-4-methoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-methoxybenzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

54
[ 481-72-1 ]
[ 943-89-5 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(4-methoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-3-(4-methoxyphenyl)acrylic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

55
[ 481-72-1 ]
[ 27542-85-4 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(4-acetoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-acetoxycinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

56
[ 2345-34-8 ]
[ 481-72-1 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 4-acetoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-acetyloxy-benzoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

57
[ 481-72-1 ]
[ 93-07-2 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3,4-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Veratric acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

58
[ 481-72-1 ]
[ 118-41-2 ]
(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3,4,5-trimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: Eudesmic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

59
[ 481-72-1 ]
[ 14737-89-4 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(3,4-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-dimethoxy-trans-cinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

60
[ 481-72-1 ]
(E)-3,4,5-trimethoxy-cinnamic acid [ No CAS ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3-(3,4,5-trimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-3,4,5-trimethoxy-cinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

61
[ 481-72-1 ]
[ 20767-04-8 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3-(3,5-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 269 - 276

62
[ 481-72-1 ]
[ 16909-09-4 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3-(2,4-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (E)-3-(2,4-dimethoxyphenyl)-2-propenoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

63
[ 481-72-1 ]
[ 7345-82-6 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(2,3-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2,3-dimethoxycinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

64
[ 481-72-1 ]
[ 38489-74-6 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl-3-(2,5-dimethoxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: trans-2,5-dimethoxycinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

65
[ 481-72-1 ]
[ 2373-80-0 ]
(E)-(1,8-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-3-yl)methyl 3-(3,4-methylenedioxyphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,4-methylenedioxy-trans-cinnamic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione In dichloromethane at 20℃;	General procedure for synthesis of ester derivatives of aloe-emodin General procedure: Substituted benzoic acids or cinnamic acids (0.1 mmol) in dry CH2Cl2 (0.2 mL) were treated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI, 20.6 mg, 0.1 mmol) and DMAP (1.0 mg, 0.006 mmol). The mixtures were stirred at room temperature for 5 min. Aloe-emodin (2, 5.4 mg, 0.02 mmol) was added, and stirring was continued at room temperature until the starting compound was consumed. The resulting solution was diluted with EtOAc (10 mL) and concentrated on a rotary evaporator. The final benzoate and cinnamate derivatives of aloe-emodin were purifiedby using preparative TLC (silica gel, 500 m; hexane/EtOAc, 4:1).

Reference： [1]Dai, Yumin; Harinantenaina, Liva; Bowman, Jessica D.; Da Fonseca, Isabel Osorio; Brodie, Peggy J.; Goetz, Michael; Cassera, Maria B.; Kingston, David G.I. [Bioorganic and Medicinal Chemistry, 2014, vol. 22, # 1, p. 269 - 276]

66
[ 481-72-1 ]
uridine-5′-diphosphoglucuronic acid [ No CAS ]
aloe-emodin-1-O-β-D-glucuronide [ No CAS ]
[ 1258865-27-8 ]

Yield	Reaction Conditions	Operation in experiment
	With recombinant human UGT 1A₉ isoform at 37℃; for 4h; Enzymatic reaction;	Isolation of anthraquinone glucuronides General procedure: The glucuronides of aloe-emodin (AEG1, AEG2), emodin (EG3), chrysophanol (CG1, CG2) and physcion (PG1, PG2) were prepared from scale-up reaction. The reaction system consisted of 0.2mg/mL aloe-emodin or emodin, or 0.05mg/mL chrysophanol or physcion, 0.2mgprotein/mL RLMs, 1mM UDPGA, in a final volume of 100mL (aloe-emodin or emodin) or 20mL (chrysophanol or physcion) and was incubated at 37°C for 4h. The reactions were stopped and samples were prepared in the same manner as described above before being injected to a semi-preparative HPLC-UV instrument. Samples were eluted using an Agilent Zobrax SB-C18 column (5μm, 250mm×9.4mm). The mobile phases consisted of 0.1% aqueous formic acid (A) and acetonitrile (B) and eluted isocratically at 2.5mL/min as follows: AEG1 and AEG2 45% B, EG3 55% B, CG1 and CG2 62% B, PG1 and PG2 68% B. The eluent containing each metabolite was collected, evaporated under nitrogen to remove acetonitrile followed by freeze drying.

Reference： [1]Wu, Wenjin; Hu, Nan; Zhang, Qingwen; Li, Yaping; Li, Peng; Yan, Ru; Wang, Yitao [Chemico-Biological Interactions, 2014, vol. 219, p. 18 - 27]

67
[ 481-72-1 ]
[ 17178-10-8 ]
3-(hydroxymethyl)-1,8-bis(2-methoxyethoxy)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.7%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h;	The general procedures for the synthesis of 1, 8-alkoxy substituted aloe-emodin (1-4) B Procedure: 6g (0.15mol) of sodium hydroxide was dissolved in 20 mL of water and cooled to room temperature. 2-Methoxyethanol (15.22g, 0.2mol) was added to the solution and stirred for 30 min at 0oC. Tosyl chloride (19.1g, 0.1mol) in 25 mL of dry THF was added to the reaction mixture by dropwise, then the mixture was stirred for 5h at 0oC.The appearing precipitate was filtered and washed with ether, the filtrate was extracted by ether (2×20 mL). The combined organic phases were washed with brine and dried by anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to get 2-methoxyethyl 4-methylbenzenesulfonate. 2-Methoxyethyl 4-methylbenzenesulfonate (2.3g, 0.01mol) in 30mL of dry DMF was added to a 50 mL dry flask. Aloe-emodin (2.7g, 0.01mol) and anhydrous potassium carbonate (6.9 g, 0.05 mol) were added to the solution and stirred for 16h at 80oC. The reaction mixture was cooled to room temperature and poured into 80mL of water. The mixture was extracted with DCM (3×30mL). The combined organic phases were washed with brine and dried by anhydrous sodium sulfate, the solvent was evaporated under reduced pressure to get crude product, which was purified by column chromatography with ethyl acetate in petroleum ether.

Reference： [1]Liu, Jinbing; Wu, Fengyan; Chen, Changhong [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5142 - 5146]

68
[ 481-72-1 ]
1,8-bis(allyloxy)-3-(hydroxymethyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.7%	With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 20h;	The general procedures for the synthesis of 1, 8-alkoxy substituted aloe-emodin (1-4) General procedure: A Procedure: 1.08g (4 mmol) of aloe-emodin was dissolved in 50mL of dry DMF and added to a 100 mL dry flask. 9.6 mmol of halohydrocarbon was added to the mixture. Under intensive stirring conditions, anhydrous potassium (16 mmol) carbonate was added to the above reaction mixture and warm up to 55oC. The reaction mixture was stirred at the temperature for further about 20h, and the reaction process was monitored by TLC (EtOAc/PE (60-90oC) = 1:2). When no starting material could be detected, the reaction mixture was cooled to room temperature. The solution was poured into water (40 mL). The water layer was extracted by ethyl acetate (3 × 30 mL), the organic layer was merged and washed with water (3 × 30mL). The organic layer was dried with anhydrous sodium sulfate and evaporated under reduced pressure to get the crude product, which was purified by column chromatography with ethyl acetate in petroleum ether.

Reference： [1]Liu, Jinbing; Wu, Fengyan; Chen, Changhong [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5142 - 5146]

69
[ 481-72-1 ]
[ 50488-95-4 ]

Yield	Reaction Conditions	Operation in experiment
53.1%	With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 20h;	The general procedures for the synthesis of 1, 8-alkoxy substituted aloe-emodin (1-4) General procedure: A Procedure: 1.08g (4 mmol) of aloe-emodin was dissolved in 50mL of dry DMF and added to a 100 mL dry flask. 9.6 mmol of halohydrocarbon was added to the mixture. Under intensive stirring conditions, anhydrous potassium (16 mmol) carbonate was added to the above reaction mixture and warm up to 55oC. The reaction mixture was stirred at the temperature for further about 20h, and the reaction process was monitored by TLC (EtOAc/PE (60-90oC) = 1:2). When no starting material could be detected, the reaction mixture was cooled to room temperature. The solution was poured into water (40 mL). The water layer was extracted by ethyl acetate (3 × 30 mL), the organic layer was merged and washed with water (3 × 30mL). The organic layer was dried with anhydrous sodium sulfate and evaporated under reduced pressure to get the crude product, which was purified by column chromatography with ethyl acetate in petroleum ether.

Reference： [1]Liu, Jinbing; Wu, Fengyan; Chen, Changhong [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5142 - 5146]

70
[ 481-72-1 ]
1,8-dibutoxy-3-(hydroxymethyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
9.3%	With potassium carbonate In N,N-dimethyl-formamide at 55℃; for 20h;	The general procedures for the synthesis of 1, 8-alkoxy substituted aloe-emodin (1-4) General procedure: A Procedure: 1.08g (4 mmol) of aloe-emodin was dissolved in 50mL of dry DMF and added to a 100 mL dry flask. 9.6 mmol of halohydrocarbon was added to the mixture. Under intensive stirring conditions, anhydrous potassium (16 mmol) carbonate was added to the above reaction mixture and warm up to 55oC. The reaction mixture was stirred at the temperature for further about 20h, and the reaction process was monitored by TLC (EtOAc/PE (60-90oC) = 1:2). When no starting material could be detected, the reaction mixture was cooled to room temperature. The solution was poured into water (40 mL). The water layer was extracted by ethyl acetate (3 × 30 mL), the organic layer was merged and washed with water (3 × 30mL). The organic layer was dried with anhydrous sodium sulfate and evaporated under reduced pressure to get the crude product, which was purified by column chromatography with ethyl acetate in petroleum ether.

Reference： [1]Liu, Jinbing; Wu, Fengyan; Chen, Changhong [Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 22, p. 5142 - 5146]

71
[ 481-72-1 ]
[ 13739-02-1 ]

Reference： [1]Patent: CN108218701,2018,A

72
[ 518-82-1 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: pyridine / 4 h / 70 °C 2: acetic anhydride; acetic acid; chromium(VI) oxide / 24 h / 70 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 4: potassium hydroxide / 0.75 h / 70 °C 5: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction
	Multi-step reaction with 7 steps 1: pyridine / 4 h / 70 °C 2: acetic anhydride; acetic acid; chromium(VI) oxide / 24 h / 70 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 4: potassium hydroxide / 0.75 h / 70 °C 5: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction 6: acetic acid; lead(IV) tetraacetate / 0.33 h / 0 °C 7: [⁽²⁾H₆]acetone / 18 h
	Multi-step reaction with 6 steps 1: pyridine / 70 °C 2: acetic anhydride; chromium(VI) oxide; acetic acid / 70 °C 3: dimethylsulfide borane complex / 0 °C 4: potassium hydroxide / 70 °C 5: β-D-glucose; nicotinamide adenine dinucleotide phosphate; sodium dithionite; glucose dehydrogenase; Talaromyces islandicus anthrol reductase / aq. phosphate buffer; dimethyl sulfoxide / 14 h / pH 7 / Inert atmosphere; Enzymatic reaction 6: acetic acid; lead(IV) tetraacetate / 0 - 20 °C

Multi-step reaction with 6 steps 1: pyridine / 70 °C 2: acetic anhydride; chromium(VI) oxide; acetic acid / 70 °C 3: dimethylsulfide borane complex / tetrahydrofuran / 0 °C 4: potassium hydroxide / 70 °C 5: NADP; D-glucose; glucose dehydrogenase; ethylenediaminetetraacetic acid; dithiothreitol; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 12 h / 30 °C / pH 7 / Enzymatic reaction 6: sulfuric acid / methanol / 12 h / 70 °C

Reference： [1]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[2]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[3]Mondal, Amit; Singh, Shailesh Kumar; Manna, Tanaya; Husain, Syed Masood [Chemical Communications, 2020, vol. 56, # 22, p. 3337 - 3340]
[4]Das, Kiran; De, Arijit; Husain, Syed Masood; Maity, Biswanath; Mondal, Amit; Rajput, Anshul [New Journal of Chemistry, 2022, vol. 46, # 7, p. 3087 - 3090]

73
[ 6030-60-0 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: acetic anhydride; acetic acid; chromium(VI) oxide / 24 h / 70 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 3: potassium hydroxide / 0.75 h / 70 °C 4: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction
	Multi-step reaction with 6 steps 1: acetic anhydride; acetic acid; chromium(VI) oxide / 24 h / 70 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 3: potassium hydroxide / 0.75 h / 70 °C 4: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction 5: acetic acid; lead(IV) tetraacetate / 0.33 h / 0 °C 6: [⁽²⁾H₆]acetone / 18 h
	Multi-step reaction with 5 steps 1: acetic anhydride; chromium(VI) oxide; acetic acid / 70 °C 2: dimethylsulfide borane complex / 0 °C 3: potassium hydroxide / 70 °C 4: β-D-glucose; nicotinamide adenine dinucleotide phosphate; sodium dithionite; glucose dehydrogenase; Talaromyces islandicus anthrol reductase / aq. phosphate buffer; dimethyl sulfoxide / 14 h / pH 7 / Inert atmosphere; Enzymatic reaction 5: acetic acid; lead(IV) tetraacetate / 0 - 20 °C

Multi-step reaction with 5 steps 1: acetic anhydride; chromium(VI) oxide; acetic acid / 70 °C 2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C 3: potassium hydroxide / 70 °C 4: NADP; D-glucose; glucose dehydrogenase; ethylenediaminetetraacetic acid; dithiothreitol; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 12 h / 30 °C / pH 7 / Enzymatic reaction 5: sulfuric acid / methanol / 12 h / 70 °C

Reference： [1]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[2]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[3]Mondal, Amit; Singh, Shailesh Kumar; Manna, Tanaya; Husain, Syed Masood [Chemical Communications, 2020, vol. 56, # 22, p. 3337 - 3340]
[4]Das, Kiran; De, Arijit; Husain, Syed Masood; Maity, Biswanath; Mondal, Amit; Rajput, Anshul [New Journal of Chemistry, 2022, vol. 46, # 7, p. 3087 - 3090]

74
[ 61350-19-4 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 2: potassium hydroxide / 0.75 h / 70 °C 3: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction
	Multi-step reaction with 5 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 0.25 h / 0 °C 2: potassium hydroxide / 0.75 h / 70 °C 3: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction 4: acetic acid; lead(IV) tetraacetate / 0.33 h / 0 °C 5: [⁽²⁾H₆]acetone / 18 h
	Multi-step reaction with 4 steps 1: dimethylsulfide borane complex / 0 °C 2: potassium hydroxide / 70 °C 3: β-D-glucose; nicotinamide adenine dinucleotide phosphate; sodium dithionite; glucose dehydrogenase; Talaromyces islandicus anthrol reductase / aq. phosphate buffer; dimethyl sulfoxide / 14 h / pH 7 / Inert atmosphere; Enzymatic reaction 4: acetic acid; lead(IV) tetraacetate / 0 - 20 °C

Multi-step reaction with 4 steps 1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C 2: potassium hydroxide / 70 °C 3: NADP; D-glucose; glucose dehydrogenase; ethylenediaminetetraacetic acid; dithiothreitol; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 12 h / 30 °C / pH 7 / Enzymatic reaction 4: sulfuric acid / methanol / 12 h / 70 °C

Reference： [1]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[2]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[3]Mondal, Amit; Singh, Shailesh Kumar; Manna, Tanaya; Husain, Syed Masood [Chemical Communications, 2020, vol. 56, # 22, p. 3337 - 3340]
[4]Das, Kiran; De, Arijit; Husain, Syed Masood; Maity, Biswanath; Mondal, Amit; Rajput, Anshul [New Journal of Chemistry, 2022, vol. 46, # 7, p. 3087 - 3090]

75
[ 195454-66-1 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium hydroxide / 0.75 h / 70 °C 2: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction
	Multi-step reaction with 4 steps 1: potassium hydroxide / 0.75 h / 70 °C 2: β-D-glucose; NADPH; glucose dehydrogenase; polyhydroxyanthracene reductase from Cochliobolus lunatus; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 24 h / Inert atmosphere; Enzymatic reaction 3: acetic acid; lead(IV) tetraacetate / 0.33 h / 0 °C 4: [⁽²⁾H₆]acetone / 18 h
	Multi-step reaction with 3 steps 1: potassium hydroxide / 70 °C 2: β-D-glucose; nicotinamide adenine dinucleotide phosphate; sodium dithionite; glucose dehydrogenase; Talaromyces islandicus anthrol reductase / aq. phosphate buffer; dimethyl sulfoxide / 14 h / pH 7 / Inert atmosphere; Enzymatic reaction 3: acetic acid; lead(IV) tetraacetate / 0 - 20 °C

Multi-step reaction with 3 steps 1: potassium hydroxide / 70 °C 2: NADP; D-glucose; glucose dehydrogenase; ethylenediaminetetraacetic acid; dithiothreitol; sodium dithionite / aq. phosphate buffer; dimethyl sulfoxide / 12 h / 30 °C / pH 7 / Enzymatic reaction 3: sulfuric acid / methanol / 12 h / 70 °C

Reference： [1]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[2]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]
[3]Mondal, Amit; Singh, Shailesh Kumar; Manna, Tanaya; Husain, Syed Masood [Chemical Communications, 2020, vol. 56, # 22, p. 3337 - 3340]
[4]Das, Kiran; De, Arijit; Husain, Syed Masood; Maity, Biswanath; Mondal, Amit; Rajput, Anshul [New Journal of Chemistry, 2022, vol. 46, # 7, p. 3087 - 3090]

76
[ 481-73-2 ]
[ 481-72-1 ]
(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 79% 2: 10%	With glucose dehydrogenase; sodium dithionite; β-D-glucose; Talaromyces islandicus anthrol reductase; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; dimethyl sulfoxide for 14h; Inert atmosphere; Enzymatic reaction; stereoselective reaction;
1: 74% 2: 8%	With glucose dehydrogenase; sodium dithionite; β-D-glucose; polyhydroxyanthracene reductase from Cochliobolus lunatus; NADPH In aq. phosphate buffer; dimethyl sulfoxide for 24h; Inert atmosphere; Enzymatic reaction;

Reference： [1]Mondal, Amit; Singh, Shailesh Kumar; Manna, Tanaya; Husain, Syed Masood [Chemical Communications, 2020, vol. 56, # 22, p. 3337 - 3340]
[2]Mondal, Amit; Saha, Nirmal; Rajput, Anshul; Singh, Shailesh Kumar; Roy, Brindaban; Husain, Syed Masood [Organic and Biomolecular Chemistry, 2019, vol. 17, # 38, p. 8711 - 8715]

77
[ 133-89-1 ]
[ 481-72-1 ]
[ 50488-89-6 ]

Yield	Reaction Conditions	Operation in experiment
4.5 mg	With glycosyltransferases YojK bacillus licheniformi; magnesium chloride In dimethyl sulfoxide at 30℃; for 3h; Enzymatic reaction;

Reference： [1]Pandey, Ramesh Prasad; Bashyal, Puspalata; Parajuli, Prakash; Yamaguchi, Tokutaro; Sohng, Jae Kyung [Organic Letters, 2019, vol. 21, # 19, p. 8058 - 8064]

78
[ 1070-34-4 ]
[ 481-72-1 ]
C₂₁H₁₈O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.5922 g	With sulfuric acid; at 100℃; for 2h;	In a round-bottomed flask, 5 g of succinic anhydride and 8 ml of absolute ethanol were added, and the mixture was heated under reflux at 90 C for 3 h to recover excess ethanol to obtain a pale yellow oily substance, namely monoethyl succinate (6.5 g, 89%). The product was directly reacted without isolation.In a round-bottomed flask, 1 g of aloe-emodin and 6 g of the above monoethyl succinate were added, and 0.1 ml of sulfuric acid was slowly added dropwise, and the reaction was performed at 100 C. for 2 hours using a heating mantle.The product was dissolved in 15 ml of dichloromethane and sonicated for 5 min, then the insoluble matter was removed by suction filtration.The dichloride solution was extracted 4 times with 60 ml of a 2.5% sodium bicarbonate solution, and extracted twice with 30 mL of pure water, and the dichloromethane layer was taken.The dichloromethane was recovered to obtain a crude aloe-emodin succinyl ethyl ester.Separation by column chromatography, silica gel column chromatography with dichloromethane: ethyl acetate = 6: 1 as eluent, take the first large color band (can be analyzed by thin layer plate), and recover the solvent.Petroleum ether cleaning: Five times the volume of petroleum ether was added to the above product for cleaning and suction filtration. The filter cake was washed twice with petroleum ether to obtain pure aloe-emodin succinyl ethyl ester as a yellow powder (0.5922 g, 42.3%).

Reference： [1]Patent: CN110563587,2019,A .Location in patent: Paragraph 0054-0058

79
[ 6155-37-9 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
65%	With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; for 2h; Reflux;	Synthesis of 1,8-Dihydroxy-3-(hydroxymethyl)anthracene-9,10-dione (24) Into a 100 ml round-bottom flask, 0.1 g of 23 (0.34 mmol) was dissolved in 5 ml of THF. Then, 0.026 g of LiAlH4 was added at 0 °C and the mixture was stirred at reflux and stirring continued for about 2 h. At the consumption of the starting material, the mixture was cooled to 0 °C and acidified with dilute H2SO4 (1 ml). Then, the reaction mixture was extracted with DCM (50 ml) and washed with brine (100 ml) and dried over anhydrous sodium sulfate. The solvent was removed, and the crude product was purified by silica-gel column chromatography (DCM /MeOH, 150/1). The desired product was isolated as a yellow solid (0.066 g). Yield: 65%. 1H NMR (DMSO-d6) δ 11.93 (s, 1H), 11.87 (s, 1H), 7.78 (t, J = 7.9 Hz, 1H), 7.72-7.62 (m, 2H), 7.55 (s, 1H), 7.35 (dd, J = 8.4, 1.2 Hz, 1H), 7.25 (d, J = 1.5 Hz, 1H), 5.60 (s, 1H), 4.62 (s, 2H). 13C NMR (DMSO-d6) δ 192.0, 181.8, 162.0, 161.7, 154.1, 137.7, 133.7, 133.4, 124.8, 121.1, 119.7, 117.5, 116.2, 114.8, 62.5. HRMS (ESI) m/z: Calculated for C15H11O5 [M + H]+ 271.0599; Found 271.0601.

Reference： [1]Agbowuro, Ayodeji A.; Anifowose, Abiodun; Lu, Wen; Tan, Chalet; Tripathi, Ravi; Wang, Binghe; Yang, Xiaoxiao [Medicinal Chemistry Research, 2020, vol. 29, # 7, p. 1199 - 1210]

80
[ 481-72-1 ]
[ 106-96-7 ]
C₁₈H₁₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
331 mg	With potassium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 5h;	Synthesis of the anthraquinones E-1 (9) and AE-1 (10) Each of the compounds E (1.85 mmol) and AE (1.11 mmol) was dissolved in DMF (5 mL) in separate reaction flask with a magnetic stirrer at laboratory temperature. There after, 3-bromoprop-1-yne (8, 1.85 and 1.11 mmol) and K2CO3 (4.60 and 2.76 mmol) were put into reaction flasks of E and AE separately. Then, the reaction mixture was stirred at 60-70 °C for 5 h. The reaction flasks were cooled to laboratory temperature and extracted with EtOAc (3 × 25 mL). The organic phase was dried over anhydrous Na2SO4 and its solvent was removed in vacuo. The compounds E-1 and AE-1 were purified from the crude product mixtures E-1 (512 mg) and AE-1 (331 mg), respectively (Fig. S4A). Purification of the products were performed using the silica gel column (25 g) and the mobile phase of EtOAc:n-C6H12 (1:1; v:v).

Reference： [1]Gecibesler, Ibrahim Halil; Disli, Faruk; Bayindir, Sinan; Toprak, Mahmut; Tufekci, Ali Riza; Sahin Yaglıoglu, Ayse; Altun, Muhammed; Kocak, Alpaslan; Demirtas, Ibrahim; Adem, Sevki [Food Chemistry, 2021, vol. 342]

81
[ 481-72-1 ]
[ 20277-69-4 ]
1,8-dihydroxy-3-((methylsulfonyl)methyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With boron trifluoride diethyl etherate; acetic acid at 20℃;	5.2. General preparation of compounds (3a-i) General procedure: The respective benzyl alcohol (1.96 μmol) was dissolved in acetic acid (3 mL). BF3.OEt2 (3.5 mL, 3.528 μmol) was added to the reaction mixture at room temperature. Sodium methyl sulfinate (200 mg, 1.96 μmol) was added to the reaction mixture and stirred for 30 min. Reaction mixture completion was confirmed by the TLC. After completion of the reaction, the reaction mixture was quenched with NaHCO3 solution (10 mL). The organic compound was extracted with dichloromethane (20 mL) and water (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by the silica gel chromatography to give the compounds 3a-3i. Yield, IR, NMR, ESI MS (M+H) data, and CHNS/O elemental analysis (Perkin-Elmer 2400) data of each product are given below.

Reference： [1]Bollikolla, Hari Babu; Dasireddy, Chandra Rao; Kotra, Vijay; Ravi Kumar, Gollapudi; Varala, Ravi [Turkish Journal of Chemistry, 2020, vol. 44, # 5, p. 1386 - 1394]

82
[ 154658-30-7 ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate In ethyl acetate at 20℃; for 1h;	5.1. General preparation of compounds (1a-1i) General procedure: NaBH4 (4.76 μmol) was added to the ethyl alcohol (3 mL) and the reaction mixture was stirred at room temperature for 5 min. Respectively, aldehyde compound (4.76 μmol) was added to the reaction mixture and stirred continuously for 1 h. Reaction mixture completion was confirmed by the TLC. After completion of the reaction, the mixture was quenched with 10% HCl (3 mL) and ethanol was evaporated under reduced pressure. After the complete removal of ethanol, saturated sodium bisulfite (1 5 mL) was added. The organic compound was extracted with dichloromethane (20 mL) and water (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure; to give 1a-1i compounds. Yield, 1H NMR, ESI-MS (M+H) data of all compounds, and CHNS/O elemental analysis (Perkin-Elmer 2400, PerkinElmer Inc., Waltham, MA, USA) composition data of each product are given below.

Reference： [1]Bollikolla, Hari Babu; Dasireddy, Chandra Rao; Kotra, Vijay; Ravi Kumar, Gollapudi; Varala, Ravi [Turkish Journal of Chemistry, 2020, vol. 44, # 5, p. 1386 - 1394]

83
(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one [ No CAS ]
[ 481-72-1 ]
(−)-flavoskyrin C [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 58% 2: 18%	With oxygen In aq. phosphate buffer; acetonitrile at 10℃;

Reference： [1]Mondal, Amit; De, Arijit; Husain, Syed Masood [Organic Letters, 2020, vol. 22, # 21, p. 8511 - 8515]

84
[ 481-72-1 ]
C₁₅H₁₂O₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With oxygen; dioxygenase GedK from Aspergillus terreus AT₀₁; reductase GedF from Aspergillus terreus AT₀₁; NADPH In aq. buffer at 28℃; for 13h; Enzymatic reaction;

Reference： [1]Geng, Ce; Huang, Xuenian; Lu, Xuefeng; Qi, Feifei; Sun, Jia; Xue, Yingying; Zhang, Wei [Journal of the American Chemical Society, 2021, vol. 143, # 40, p. 16326 - 16331]

85
(R)-3,8,9,10-tetrahydroxy-6-(hydroxymethyl)-3,4-dihydroanthracen-1(2H)-one [ No CAS ]
[ 481-72-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid In methanol at 70℃; for 12h;

Reference： [1]Das, Kiran; De, Arijit; Husain, Syed Masood; Maity, Biswanath; Mondal, Amit; Rajput, Anshul [New Journal of Chemistry, 2022, vol. 46, # 7, p. 3087 - 3090]

86
[ 481-72-1 ]
1-(8-methyltosylaminoethynylnaphthyl) 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside [ No CAS ]
aloe-emodin-ω-O-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione With N,O-Bis(trimethylsilyl)trifluoroacetamide In dichloromethane at 60℃; Inert atmosphere; Stage #2: 1-(8-methyltosylaminoethynylnaphthyl) 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside With trimethylsilyl trifluoropmethanesulfonate In dichloromethane at 60℃; for 2h; Inert atmosphere; Molecular sieve;	1-(2-O-Benzoyl-3,4,6-tri-O-benzyl-b-D-glucopyranosyl)uracil (17) General procedure: To a stirred suspension of uracil (4 mg, 0.036 mmol) in dry dichloromethane(1 mL) was added BSTFA (40 mL, 0.15 mmol). The suspension wasthen heated to 60 C (by an oil bath) and the stirring was continued until aclear solution was obtained. The reaction mixture was then cooled to roomtemperature, to which the freshly activated powdered AW MS-300 as wellas 16 (50 mg, 0.056 mmol) were added sequentially at room temperatureunder N2 atmosphere. The resulting suspension was stirred at the sametemperature for 30 min before TMSOTf (2 mL, 0.011 mmol) was addedunder N2 atmosphere. The stirring was continued for another 2 h at 60 Cbefore Et3N was added to quench the reaction. Filtration was followed byconcentration in vacuo to provide a residue, which was further purified bysilica gel column chromatography (petroleum ether/ethyl acetate 1: 1) toprovide 17 (21 mg, 86%) as a white solid: [a]D25 31.2 (c 1.0, CHCl3);1H NMR (400 MHz, CDCl3) d 8.49 (d, J2.4 Hz, 1 H), 7.91 (dd, J1.2,8.4 Hz, 2 H), 7.53-7.49 (m, 1 H), 7.41-7.28 (m, 11 H), 7.19-7.10 (m, 2 H),7.14-7.07 (m, 5 H), 5.90 (d, J9.2 Hz, 1 H), 5.76 (dd, J2.0, 8.0 Hz, 1 H),5.37 (t, J9.2 Hz, 1 H), 4.85 (d, J10.8 Hz, 1 H), 4.78 (d, J10.8 Hz, 1 H),4.67 (d, J11.2 Hz, 1 H), 4.61 (d, J10.8 Hz, 1 H), 4.57 (d, J12.4 Hz,1 H), 4.52 (d, J12.4 Hz, 1 H), 4.00 (t, J8.8 Hz, 1 H), 3.87 (t, J9.2 Hz,1 H), 3.76-3.68 (m, 3 H); 13C NMR (100 MHz, CDCl3) d 165.4, 162.9,150.5, 139.7, 137.7, 137.6, 137.4, 133.7, 129.9, 128.6 (2C), 128.5, 128.4,128.1 (2C), 127.9, 127.8, 103.5, 82.7, 80.5, 77.9, 77.3, 75.5, 75.3, 73.5, 71.9,68.1; HRMS (ESI) m/z calcd for C38H36O8N2Na [MNa]: 671.2364;found: 671.2360.

Reference： [1]Zhou, Si-Yu; Liu, Hui-Juan; Zhang, Qing-Ju; Liao, Jin-Xi; Liu, De-Yong; Li, Ming-Dong; Sun, Jian-Song [Journal of Carbohydrate Chemistry, 2022, vol. 41, # 2-3, p. 181 - 206]

87
[ 481-72-1 ]
[ 100-39-0 ]
[ 1204745-87-8 ]

Yield	Reaction Conditions	Operation in experiment
61%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 5h;	4.2.3.9. 1,8-bis(benzyloxy)-3-(hydroxymethyl)anthracene-9,10-dione. Benzyl bromide (599 mg, 3.5 mmol) was added dropwise to a solution ofaloe-emodin (270 mg, 1 mmol), KI (17 mg, 0.1 mmol) and K2CO3 (483mg, 3.5 mmol) in dry DMF (3 mL) at 0 °C, and the reaction mixture was heated to 80 °C for 5 h. Upon completion, the reaction mixture was diluted with water and extracted three times with ethyl acetate. The organic layers were dried with dry Na2SO4 and filtered, and the filtrate was removed under reduced pressure. The residue was purified by column chromatography to give Compound 4.Yellow solid. Yield: 61%. mp: 183.6-184.7 °C; 1H NMR (600 MHz,CDCl3) δ 7.84 (dd, J = 7.7, 0.7 Hz, 1H), 7.74 (s, 1H), 7.66-7.62 (m, 4H),7.59 (dd, J = 8.2, 7.7 Hz, 1H), 7.43-7.38 (m, 5H), 7.35-7.31 (m, 3H),5.32 (s, 2H), 5.29 (s, 2H), 4.77 (d, J = 6.0 Hz, 2H), 2.09 (t, J = 6.0 Hz,1H); 13C NMR (150 MHz, CDCl3) δ 184.1, 182.2, 158.9, 158.4, 147.6,136.7, 136.6, 135.0, 135.0, 133.9, 128.7, 127.9, 126.9, 124.9, 123.8,120.4, 119.6, 117.6, 117.0, 71.3, 71.2, 64.5.

Reference： [1]Guo, Jing; Li, Lingyu; Li, Xiaoxue; Shang, Hai; Tian, Yu; Wang, Pengtao; Zou, Zhongmei [European Journal of Medicinal Chemistry, 2022, vol. 238]

88
[ 481-72-1 ]
[ 79-04-9 ]
(4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl 2-chloroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With 4-dimethylaminopyridine; triethylamine In dichloromethane at 20℃; for 8h;	4.2.1. (4,5-dihydroxy-9,10-dioxo-9,10-dihydroanthracen-2-yl)methyl 2-chloroacetate (1) Chloroacetyl chloride (633 mg, 5.6 mmol) was added dropwise to a solution of aloe-emodin (1.0 g, 3.7 mmol), 4-dimethylaminopyridine(49 mg, 0.4 mmol) and triethylamine (1.12 g, 11.1 mmol) in CH2Cl2(200 mL) at 0 °C. After stirring at room temperature for 8 h, the reaction mixture was quenched with water, and the aqueous layer was extracted three times with CH2Cl2. The organic layers were dried with dry Na2SO4 and filtered. The filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography to give Compound 1 (Yield: 69%).

Reference： [1]Guo, Jing; Li, Lingyu; Li, Xiaoxue; Shang, Hai; Tian, Yu; Wang, Pengtao; Zou, Zhongmei [European Journal of Medicinal Chemistry, 2022, vol. 238]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

CAS No. :	481-72-1	MDL No. :	MFCD00017373
Formula :	C₁₅H₁₀O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YDQWDHRMZQUTBA-UHFFFAOYSA-N
M.W :	270.24	Pubchem ID :	10207
Synonyms :	Rhabarberone;3-Hydroxymethylchrysazine;NSC 38628

Num. heavy atoms :	20
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	1
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	69.92
TPSA :	94.83 Å²

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-6.66 cm/s

Log Po/w (iLOGP) :	1.95
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.21
Log Po/w (MLOGP) :	0.1
Log Po/w (SILICOS-IT) :	2.42
Consensus Log Po/w :	1.5

[ CAS No. 481-72-1 ] {[proInfo.proName]}

Quality Control of [ 481-72-1 ]

Related Doc. of [ 481-72-1 ]

Product Details of [ 481-72-1 ]

Calculated chemistry of [ 481-72-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 481-72-1 ]

Application In Synthesis of [ 481-72-1 ]

[ 481-72-1 ] Synthesis Path-Upstream 1~1

[ 481-72-1 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.04
Solubility :	0.246 mg/ml ; 0.000912 mol/l
Class :	Soluble
Log S (Ali) :	-3.43
Solubility :	0.1 mg/ml ; 0.00037 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.92
Solubility :	0.0322 mg/ml ; 0.000119 mol/l
Class :	Soluble

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.6

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Yield	Reaction Conditions	Operation in experiment
85%	at 120℃; for 3 h;	Example 3; Oxidizing medium was prepared by dissolving sodium nitrite (255 g) in sulphuric acid (1.2 I). The oxidizing medium was heated to 120⁰C and then aloe-emodin (100 g) was added slowly thereto. After completion of the oxidation reaction (3 hours), the reaction mixture was poured into distilled water (7.2 I) at 2°C to precipitate rhein, and rhein is filtered and dried. Rhein having a degree of purity of 90 - 95 percent was obtained in a yield of more than 85 percent.
62%	With water; pyridinium chlorochromate In N,N-dimethyl-formamide at 20℃; for 24 h;	A mixture of compound A1 (1 mmol, 0.27 g), PCC (2 mmol, 0.45 g), DMF (100 ml) and 2 mL of water were stirred at room temperature for 24 h, monitored by TLC. After the completion of reaction, 100 mL of ice water was added under stirring to afford orange precipitate. The orange precipitate was filtered, washed and dried. Recrystallization of the orange precipitate from ethanol gave compound B7 as brown acicular crystals, yield 62percent; mp 310–313 °C; IR ν_max cm⁻¹: 3432, 3059, 2930, 1695, 1628, 1270, 1192, 757; ¹H NMR (DMSO-d₆): δ = 7.58 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.85 (s, 1H, H-C(1)), 7.97 (dd, 1H, J₁ = 8.2 Hz, J₂ = 7.5 Hz, H-C(7)), 8.01 (s, 1H, H-C(3)), 8.45 (d, 1H, J = 7.5 Hz, H-C(8)), 11.87 (s, 1H, HO-C(1)), 11.94 (s, 1H, HO-C(8)), 13.90 (s, 1H, COOH); ESI-MS m/z: 285.04 [M+H]⁺.
62%	With pyridinium chlorochromate In water; N,N-dimethyl-formamide at 20℃; for 24 h;	A mixture of compound 1 (1 mmol, 0.27 g), PCC (2 mmol, 0.45 g), DMF (100 ml) and 2 mL of water were stirred at room temperature for 24 h, monitored by TLC. After the completion of reaction, 100 mL of ice water was added under stirring to afford orange precipitate. The orange precipitate was filtered, washed and dried. Recrystallization of the orange precipitate from ethanol gave compound A4 as brown acicular crystals, yield 62percent; m.p. 310-313 °C; IR ν_max cm^-1: 3432, 3059, 2930, 1695, 1628, 1270, 1192, 757; ¹H NMR (d⁶-DMSO): δ = 7.58 (d, 1H, J = 8.2 Hz, 1H, H-C(6)), 7.85 (s, 1H, H-C(1)), 7.97 (dd, 1H, J₁ = 8.2 Hz, J₂ = 7.5 Hz, H-C(7)), 8.01 (s, 1H, H-C(3)), 8.45 (d, 1H, J = 7.5 Hz, H-C(8)), 11.87 (s, 1H, HO-C(1)), 11.94 (s, 1H, HO-C(8)), 13.90 (s, 1H, COOH); HRMS (ESI): calcd for [M + H]⁺ (C₁₅H₉O₆) m/z 285.0399, found 285.0403.

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling