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CAS No. : | 122-48-5 | MDL No. : | MFCD00048232 |
Formula : | C11H14O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OJYLAHXKWMRDGS-UHFFFAOYSA-N |
M.W : | 194.23 | Pubchem ID : | 31211 |
Synonyms : |
Vanillylacetone;Gingerone;AI3-31837;NSC 15335
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 54.54 |
TPSA : | 46.53 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.7 cm/s |
Log Po/w (iLOGP) : | 2.09 |
Log Po/w (XLOGP3) : | 1.11 |
Log Po/w (WLOGP) : | 1.92 |
Log Po/w (MLOGP) : | 1.42 |
Log Po/w (SILICOS-IT) : | 2.41 |
Consensus Log Po/w : | 1.79 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.8 |
Solubility : | 3.1 mg/ml ; 0.016 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.68 |
Solubility : | 4.06 mg/ml ; 0.0209 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -3.1 |
Solubility : | 0.155 mg/ml ; 0.000796 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.52 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338-P304+P340-P405-P501 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With nickel boride; hydrogen; In methanol; at 25℃; for 1.5h; | General procedure: Sodium tetrahydridoborate, 0.46 g (12.1 mmol), was added in portions with stirring to a solution of 1.10 g (4.63 mmol) of NiCl2·6H2O in 20 mL of methanol, cooled to 0 C. The resulting suspension was stirred for 15 min at 0 C and refluxed for 20 min under argon. The mixture was then cooled to room temperature, 9.25 mmol of ketone 1a-1g was added, and the miixture was stirred in a hydrogen atmosphere. When the green color of the reaction mixture disappeared, hydrogen supply was turned off, and the mixture was filtered. The precipitate of nickel boride was additionally washed with a small amount of methanol, and the filtrate was evaporated under reduced pressure. The residue was dissolved in ethyl acetate (20 mL), the solution was washed with a saturated aqueous solution of ammonium chloride (20 mL), the organic phase was separated, and the aqueous phase was extracted with ethyl acetate (10 mL). The combined organic phases were washed with saturated solutions of NaHCO3 and NaCl (10 mL each), dried over Na2SO4, and evaporated under reduced pressure. The residue was purified by crystallization from appropriate solvent mixture or by column chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With palladium on activated charcoal; hydrogen; acetic acid; In ethanol; at 20℃; under 760.051 Torr; | 38.44 g of 4-(4-hydroxy-3-methoxyphenyl)-3-ene-2-butanone was dissolved in 500 mL of ethanol.Add 500 mL of acetic acid with stirring, and add 1.92 g of Pd/C.After the hydrogen balloon was placed, the gas was exchanged three times, and after reacting at room temperature for 1 hour,Filtration, the filtrate was evaporated to ethanol, water was added, and then extracted with ethyl acetate.The liquid phase was separated, and the organic phase was washed with a saturated NaHCO 3 solution and water, respectively.The solvent is removed by pressure reduction and separated by column chromatography.Obtained a colorless liquid of 31.07g,The yield was 87%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium bicarbonate; boron tribromide; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; dichloromethane; | Preparation Example 1 4-(3', 4'-dihydroxyphenyl)-butane-2-one <strong>[122-48-5]Zingeron</strong>e, [4-(3'-methoxy-4'-hydroxyphenyl)-butane-2-one], was dissolved in dichloromethane, to which 1.0 mol/l boron tribromide solution in dichloromethane was then added at -30 C. While stirring, the reaction mixture was gradually heated to a room temperature and allowed to react for further2 hours at the temperature. After adding ice water to the reaction mixture, an aqueous 2% sodium hydrogen carbonate solution was added. Then, the reaction mixture was extracted with ethyl acetate, and the ethyl acetate layer thus obtained was dried with anhydrous magnesium sulfate. Then, the ethyl acetate layer was vacuum condensed to obtain brown oil which was purified by silica gel chromatography, using a mixture of hexane/ethyl acetate =7/3 as a developing solvent. The white crystals thus obtained had almost no taste and no odor. Chemical structure was confirmed to be 4-(3', 4'-dihydroxyphenyl)-butane-2-one by GC-MS and NMR(see). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30.73% | With potassium tert-butylate; In tetrahydrofuran; at -78℃; for 1.5h;Inert atmosphere; | Take a dry 10 mL single-mouth round bottom flask.Compound 6a (117 mg, 0.60 mmol) was dissolved in dry tetrahydrofuran solution.Cooled at -78 C under argon protection,To the reaction system, 1.5 mL of t-BuOK (1Min THF) and hexanal (90.5 mul, 1.69 mmol) were slowly added dropwise in this order.Stirring reaction at a low temperature of -78 C for 1.5 hThe reaction mixture was quenched by adding a saturated ammonium chloride solution to the reaction system.Extracted with ethyl acetate (5 mL x 3),The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give a crude.Separated and purified by column chromatography,The pale yellow oily liquid product (54 mg, yield 30.73%) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98%; 2% | With sodium tetrahydroborate; nickel(II) chloride hexahydrate; hydrogen; In methanol; at 0 - 30℃; under 760.051 Torr;Reflux; Inert atmosphere; | NaBH4 (0:46 g, 12:1 mmol) was added portionwise at 0 C to a stirred solution of NiCl2*6H2O (1:10 g, 4:63 mmol) in methanol (20 mL). Once the addition was complete, the suspension was stirred for 15 min at 0 C followed by refluxing under argon atmosphere for 15 min. Then, the mixture was cooled to room temperature, and unsaturated ketone 3 (1:50 g, 9:25 mmol) was added. The stirred mixture was treated with hydrogen (1 atm) keeping the external temperature at 25 - 30 C. Once the green color of the methanolic solution had disappeared (about 1 - 2 h), the hydrogenation was stopped, and the mixture was filtered. The nickel boride cake was washed with methanol, and the combined filtrates were evaporated under reduced pressure. Then, the residue was treated with saturated aqueous NH4Cl (20 mL) and ethyl acetate (20 mL). The organic phase was separated, and the aqueous phase was extracted with ethyl acetate (10 mL). The combined organic phases were washed with brine (10 mL), dried with Na2SO4, and evaporated under reduced pressure. According to GC analysis, the unpurified reaction mixture contained > 98% of product 1 (tR =21:3 min), 1% of by product 5 (tR =21:6 min) and traces of starting enone 3 (tR =25:5 min). The residue was recrystallized from a mixture of methanol=water (1 : 3) to give pure raspberry ketone1 in a yield of 1:14 g (75%) as colorless crystals;m. p. 82 - 83 C (lit. [12]: m. p. 80 - 82 C). Alternatively, the residue was recrystallized from the mixture of toluene ethyl acetate (4 : 1), the yield of compound 1 being 1:08 g (71%), m. p. 81 - 83 C. - IR (KBr): n =3373 (OH), 1691 (C=O) cm1. - 1H NMR (400 MHz, CDCl3): d =2.14 (s,3H, CH3), 2.71 - 2.76 (m, 2H, CH2), 2.80 - 2.85 (m, 2H,CH2), 6.29 (br s, 1H, OH), 6.75 - 6.79 (m, 2H, aromaticCH), 7.00 - 7.04 (m, 2H, aromatic CH) ppm. The spectral data were similar to those reported in the literature [12, 20]. -MS: m=z (%)=164 (20) [M]+, 149 (5) [M-CH3]+, 131 (3)[M-CH3-H2O]+, 121 (11) [M-CH3CO]+, 107 (100) [M-CH3COCH2]+. - C10H12O2 (164.2): calcd. C 73.15, H 7.37; found C 73.28, H 7.28. |
68%; 19% | With diphenyl diselenide; hypophosphorous acid; In glycerol; at 90℃; for 0.5h;Inert atmosphere; | General procedure: General procedure for the synthesis of zingerone usingPhSeSePh/glycerol/H3PO2Glycerol (1.0 mL) was added to a 5 mL round-bottomedflask containing 2-methoxy-4-(3-oxo-1-butenyl)phenol 1l(0.5 mmol), diphenyl diselenide 2 (0.5 mmol) and H3PO2(0.2 mL). The reaction mixture was stirred at 90 C undernitrogen atmosphere for 30 min. After that, the reactionmixture was received in water (20 mL), extracted with ethylacetate (3 × 5 mL), dried over MgSO4, and concentratedunder vacuum. The residue was purified by columnchromatography on silica gel using ethyl acetate/hexane(10:90) as the eluent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With sodium tetrahydroborate; In methanol; at 20℃; for 2.5h;Enzymatic reaction; | <strong>[122-48-5]Zingeron</strong>e 1 (1.0g, 5.3mmol) in MeOH (2mL) was added to the suspension of NaBH4 (150mg, 3.9mmol) in MeOH (1mL) and stirred at room temperature for 2.5h. After consumption of the substrate, H2O (10mL) was added to the reaction mixture. The aqueous solution was extracted with ethyl acetate (3×10mL). The combined organic extracts were washed with brine (3×30mL), dried over Na2SO4, and concentrated on a rotary evaporator to obtain a white solid. Chromatography on silica gel, eluting with a 4:1 mixture of hexane and ethyl acetate, afforded racemic 2 quantitatively as a white solid. Structural data were confirmed when compared with known data.14 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With pyridinium p-toluenesulfonate; In dichloromethane; at 20℃; for 24h; | 3,4-Dihydro-2H-pyran (DHP) (1.77 mL, 19.5 mmol) and pyridinium p-toluenesulfonate (PPTS) (163.3 mg, 0.65 mmol) was added to a solution of zingerone (1.26 g, 6.5 mmol) in CH2Cl2 (13 mL). The reaction was stirred for 24 h at room temperature and then saturated NaHCO3 solution (20 mL) was added. The reaction mixture was extracted with CHCl3 (5 mL) three times and the combined organic phases were dried with Na2SO4 and concentrated in vacuo. Purification by column chromatography (hexane/EtOAc, 2:1) to give ZD 1 as a white solid (1.79 g, 99%). 1H NMR (400 MHz, CDCl3) delta 7.05 (d, J = 8.0 Hz, 1H), 6.75 (d, J = 2.0 Hz, 1H), 6.70 (dd, J = 2.0, 8.0 Hz, 1H), 5.36 (t, J = 3.2 Hz, 1H), 4.06-4.00 (m, 1H), 3.86 (s, 3H), 3.63-3.59 (m, 1H), 2.88-2.83 (m, 2H), 2.78-2.73 (m, 2H), 2.16 (s, 3H), 2.40-1.88 (m, 3H), 1.69-1.64 (m, 3H). 13C NMR (100 MHz, CDCl3) delta 206.9, 150.3, 144.6, 135.5, 120.3, 118.32, 112.8, 97.8, 62.2, 56.1, 45.3, 30.4, 30.1, 29.4, 25.3, 18.9. FT-IR (ATR): 2943, 1713, 1602, 1516, 1452, 1431, 1364, 1271, 1155, 1034, 967, 812 cm-1. ESI MS: m/z calcd for C16H22O4 [M+H]+ 279.16, found 279.20. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45.52 g | 38.85 g of <strong>[122-48-5]4-(4-hydroxy-3-methoxyphenyl)-2-butanone</strong> was dissolved in 500 mL of dichloromethane.Add 26 mL of tetrahydropyrrole (THP) under stirring at room temperature, and react for 15 min.The n-hexanal (15.65 g, dissolved in 100 mL of dichloromethane) was slowly added, and the reaction was continued for 18 h.Add 100mL water, add 16.00g NaOH (dissolved in 100mL water), stir at room temperature for 3h,Liquid separation. Add 3N HCl to the organic phase to pH=2-3, dispense,The organic phase is washed once and dried with anhydrous Na2SO4.The solvent was removed under reduced pressure.Obtained 45.52g of a yellow oil.The purity by HPLC was 95.34%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With trifluoroacetic acid; at 100℃; for 0.5h; | General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2-3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60-80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With trifluoroacetic acid; at 100℃; for 0.5h; | General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2-3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60-80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With trifluoroacetic acid; at 100℃; for 1.5h; | General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2-3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60-80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With trifluoroacetic acid; at 100℃; for 0.5h; | General procedure: In a typical reaction, 2-aminoacetophenone, 2-aminobenzophenone or a substituted 2-aminobenzophenone (5 mmol) was added with THC or zingerone (6 mmol) into a round-bottomed flask. To this mixture, TFA (2-3 mL) was added and stirred at 100 C for the period mentioned in Tables 1 and 2. After completion of the reaction, as indicated by TLC analysis, the reaction mixture was neutralised with 100 mL of saturated sodium bicarbonate solution. The solid that separated was filtered and washed with distilled water and dried. The resultant crude material was further purified by triturating with ethyl acetate and petroleum ether (60-80 C). It was then dried in a desiccator over fused calcium chloride for 12 h. The physical and spectroscopic data of individual pure compounds is presented below. |
Tags: 122-48-5 synthesis path| 122-48-5 SDS| 122-48-5 COA| 122-48-5 purity| 122-48-5 application| 122-48-5 NMR| 122-48-5 COA| 122-48-5 structure
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H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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