[ CAS No. 578-74-5 ] {[proInfo.proName]}

Name: 578-74-5|5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one|99+%
Brand: Ambeed
SKU: A798095
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Quality Control of [ 578-74-5 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 578-74-5 ]

Product Details of [ 578-74-5 ]

CAS No. :	578-74-5	MDL No. :	MFCD00016787
Formula :	C₂₁H₂₀O₁₀	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMOUJOKENFFTPU-QNDFHXLGSA-N
M.W :	432.38	Pubchem ID :	5280704
Synonyms :	Apigetrin;Cosmosiin;NSC 407303;Apigenin-7-O-β-D-glucoside;7-O-β-D-Glucopyranosylapigenin;Cosmosin;Thalictiin;Cosmosioside;Cosmetin;Apigenin 7-glucoside	Chemical Name :	5-Hydroxy-2-(4-hydroxyphenyl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one

Safety of [ 578-74-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 578-74-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 578-74-5 ]
Downstream synthetic route of [ 578-74-5 ]

[ 578-74-5 ] Synthesis Path-Upstream 1~14

1
[ 119249-30-8 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water; ammonium hydroxide In methanol at 20℃; for 12 h;	Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30percent aq NH₃*H₂O (5 mL) in CH₃OH (20 mL) with stirring. After stirring for 12 h at room temperature, the solvent was removed under reduced pressure. The residual was chromatographed on silica gel using ethyl acetate/MeOH (3:1) as eluent to afford the yellow solid 78 mg, yield: 72percent. Mp 234-236 °C. (lit. 13, 238-239 °C); IR (KBr, cm^-1) 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895; ¹H NMR (400 MHz, DMSO-d₆) δ 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H, H-3,4,5, 6); ¹³C NMR (100 MHz, DMSO-d₆) δ 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1; HRMS [M+Na]⁺ calcd for C₂₁H₂₀O₁₀Na 455.3665, found 455.3649.

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034
[2] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

2
[ 1145669-48-2 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium methylate In methanol; dichloromethane at 20℃;	Compound 9a (104 mg, 0.1 mmol) was dissolved in CH₂Cl₂ (2 mL) and anhydrous methanol (3 mL) was added. Sodium methoxide (100 mg, 1.85 mmol) was then added and the reaction was stirred at room temperature and monitored by TLC. Upon completion, the reaction was neutralized by adding freshly prepared 1 M HCl/MeOH solution to a pH value of 7.4. The solution was then concentrated under reduced pressure to give a yellow oil (crude product), which was further purified by preparative TLC plate to afford glycoside 9b as a white solid, 33 mg, 77percent. ¹H NMR (400 MHz, DMSO-d₆) δ 7.95 (d, J = 8.8 Hz, 2H), 6.97 (d, J = 8.8 Hz, 2H), 6.86 (s, 1H), 6.84 (d, J = 1.4 Hz, 1H), 6.44 (d, J = 1.8 Hz, 1H), 5.07 (d, J = 7.5 Hz, 1H), 3.71 (d, J = 10.7 Hz, 1H), 3.47 – 3.21 (m, 5H); ¹³C NMR (100 MHz, DMSO-d₆) δ 182.45 (C-4), 164.81 (C-7), 163.41 (C-2), 162.29 (C-5), 161.58 (C-9), 157.41 (C-4'), 129.05 (C-2',6'), 121.15 (C-1'), 116.58 (C-3',5'), 105.79 (C-10), 103.42 (C-3), 100.34 (Glc-C-1), 99.98 (C-6), 95.29 (C-8), 77.63 (Glc-C-3), 76.91 (Glc-C-5), 73.58 (Glc-C-2), 69.99 (Glc-C-4), 61.02 (Glc-C-6).

Reference： [1] Tetrahedron Letters, 2018, vol. 59, # 50, p. 4442 - 4447

3
[ 17306-46-6 ]
[ 520-36-5 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
3.4 g	Stage #1: With aluminium(III) chloride hexahydrate In methanol at 70℃; for 15 h; Sealed tube Stage #2: With phosphoric acid In methanol for 0.5 h; Sonication	5.0 g of 6H2O-aluminum trichloride, 100 ml of methanol,98percent wild luteolin 10g,70 sealed hydrolysis 15h, Adding phosphoric acid 6ml,Mixing,Ultrasound 30min,Adding 0.1percent phosphoric acid in 1000ml of the solution with stirring slowly, placing the mixture for 30 minutes, placing overnight, filtering and washing the filter cake to obtain a mixture of wild erosin, apigenin-7-O-glucoside and apigenin; The column was eluted with chloroform-methanol (12: 1), then apigenin was first eluted, and the ratio of chloroform to methanol was adjusted to (6: 1) to give apigenin-7-O- Glucoside 3.4g, determined by HPLC content of 98.3percent, and finally out of a small amount of wild lacquer glycosides

Reference： [1] Patent: CN105481916, 2016, A, . Location in patent: Paragraph 0018

4
[ 133-89-1 ]
[ 2196-14-7 ]
[ 578-74-5 ]

Reference： [1] Nature Communications, 2017, vol. 8, # 1,

5
[ 31087-58-8 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

6
[ 480-41-1 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

7
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1] Tetrahedron, 2004, vol. 60, # 9, p. 2025 - 2034

8
[ 23598-19-8 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

9
[ 52309-82-7 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

10
[ 10236-47-2 ]
[ 578-74-5 ]

Reference： [1] Carbohydrate Research, 2012, vol. 357, p. 41 - 46

11
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 30738-01-3 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580

12
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 520-36-5 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1] Liebigs Annalen der Chemie, 1992, # 6, p. 575 - 580

13
[ 123656-62-2 ]
[ 107-93-7 ]
[ 578-74-5 ]

Reference： [1] Chemistry of Natural Compounds, 1989, vol. 25, p. 303 - 308[2] Khimiya Prirodnykh Soedinenii, 1989, # 3, p. 352 - 359

14
[ 520-36-5 ]
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1] Yakugaku Zasshi, 1940, vol. 60, p. 502,505; engl. Ref. S. 190[2] Chem.Abstr., 1941, p. 4022

[ 578-74-5 ] Synthesis Path-Downstream 1~33

1
[ 77-78-1 ]
[ 578-74-5 ]
[ 70522-70-2 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1940,vol. 60,p. 502,505; engl. Ref. S. 190
Chem.Abstr.,1941,p. 4022

2
[ 520-36-5 ]
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1940,vol. 60,p. 502,505; engl. Ref. S. 190
Chem.Abstr.,1941,p. 4022

3
[ 123656-62-2 ]
[ 107-93-7 ]
[ 578-74-5 ]

Reference： [1]Chemistry of Natural Compounds,1989,vol. 25,p. 303 - 308
Khimiya Prirodnykh Soedinenii,1989,p. 352 - 359

4
anisofolin-A [ No CAS ]
[ 7400-08-0 ]
[ 578-74-5 ]

Reference： [1]Heterocycles,1982,vol. 19,p. 1655 - 1662

5
[ 108-24-7 ]
[ 578-74-5 ]
[ 60815-39-6 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 985 - 986

6
[ 578-74-5 ]
[ 74-88-4 ]
[ 70522-70-2 ]

Reference： [1]Phytochemistry,1980,vol. 19,p. 985 - 986

7
[ 578-74-5 ]
[ 2280-44-6 ]
[ 520-36-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1981,vol. 29,p. 3455 - 3463
[2]Polish Journal of Chemistry,1980,vol. 54,p. 213 - 219
[3]Polish Journal of Chemistry,1980,vol. 54,p. 213 - 219

8
apigenin 7-O-(4''-O-p-Z-coumaroyl-β-D-glucopyranoside) [ No CAS ]
[ 578-74-5 ]

Reference： [1]Phytochemistry,1986,vol. 25,p. 1770 - 1771

9
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 30738-01-3 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 575 - 580

10
[ 26544-34-3 ]
[ 2280-44-6 ]
[ 520-36-5 ]
[ 139759-42-5 ]
[ 578-74-5 ]

Reference： [1]Liebigs Annalen der Chemie,1992,p. 575 - 580

11
stachysetin [ No CAS ]
[ 578-74-5 ]
p,p'-dihydroxy-μ-truxinic acid [ No CAS ]

Reference： [1]Phytochemistry,1995,vol. 40,p. 1543 - 1548

12
apigenin 7-O-β-D-glucopyranoside-6''-(3'''-hydroxy-3'''-methyl-glutarate) [ No CAS ]
[ 578-74-5 ]

Reference： [1]Phytochemistry,1996,vol. 41,p. 643 - 646

16
[ 578-74-5 ]
[ 520-36-5 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2002,vol. 50,p. 788 - 795
[2]Chemistry of Natural Compounds,2007,vol. 43,p. 324 - 325
[3]Chemistry of Natural Compounds,2010,vol. 46,p. 454 - 455

17
[ 119249-30-8 ]
[ 578-74-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	With water; ammonium hydroxide; In methanol; at 20.0℃; for 12h;	Compound 1 (150 mg, 0.25 mmol) was added to a solution of 30% aq NH3·H2O (5 mL) in CH3OH (20 mL) with stirring. After stirring for 12 h at room temperature, the solvent was removed under reduced pressure. The residual was chromatographed on silica gel using ethyl acetate/MeOH (3:1) as eluent to afford the yellow solid 78 mg, yield: 72%. Mp 234-236 C. (lit. 13, 238-239 C); IR (KBr, cm-1) 3440, 2918, 1615, 1563, 1452, 1346, 1273, 1245, 1146, 1103, 1072, 1024, 895; 1H NMR (400 MHz, DMSO-d6) delta 12.97 (s, 1H, OH-5), 10.48 (s, 1H, OH-4'), 7.96 (d, J = 8.8 Hz, 2H, H-2', H-6'), 6.94 (d, J = 8.8 Hz, 2H, H-3', H-5'), 6.87 (s, 1H, H-3), 6.83 (d, J = 1.6 Hz, 1H, H-8), 6.45 (d, J = 1.6 Hz, 1H, H-6), 5.42 (d, J = 8.0 Hz, 1H, H-1), 5.15 (s, 1H, OH-2), 5.08 (s, 1H, OH-3), 5.06 (s, 1H, OH-4), 4.63 (s, 1H, OH-6), 3.72-3.70 (m, 1H, H-2), 3.49-3.18 (m, 5H, H-3,4,5, 6); 13C NMR (100 MHz, DMSO-d6) delta 60.6, 69.6, 73.1, 76.5, 77.2, 94.8, 99.6, 99.9, 103.1, 105.4, 116.0, 121.1, 128.6, 156.9, 161.1, 161.4, 163.0, 164.3, 180.1; HRMS [M+Na]+ calcd for C21H20O10Na 455.3665, found 455.3649.

Reference： [1]Tetrahedron,2004,vol. 60,p. 2025 - 2034
[2]Carbohydrate Research,2012,vol. 357,p. 41 - 46

18
[ 31087-58-8 ]
[ 578-74-5 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 2025 - 2034

19
[ 480-41-1 ]
[ 578-74-5 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 2025 - 2034

20
[ 572-09-8 ]
[ 578-74-5 ]

Reference： [1]Tetrahedron,2004,vol. 60,p. 2025 - 2034

21
[ 578-74-5 ]
[ 50-99-7 ]
[ 520-36-5 ]

Reference： [1]Chemistry of Natural Compounds,2009,vol. 45,p. 87 - 88
[2]Chemistry of Natural Compounds,2011,vol. 47,p. 284 - 285
[3]Chemistry of Natural Compounds,2011,vol. 47,p. 667 - 668

22
[ 23598-19-8 ]
[ 578-74-5 ]