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| CAS No.: | 480-18-2 |
|---|---|
| Name: | Taxifolin |
| Article Data: | 35 |
| Molecular Structure: | |
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| Formula: | C15H12O7 |
| Molecular Weight: | 304.256 |
| Synonyms: | 4H-1-Benzopyran-4-one,2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-, (2R-trans)-;Flavanone,3,3',4',5,7-pentahydroxy- (8CI);(+)-Dihydroquercetin;(+)-Taxifolin;(+)-trans-Taxifolin;(2R,3R)-(+)-Taxifolin;(2R,3R)-3,3',4',5,7-Pentahydroxyflavanone;(2R,3R)-Dihydroquercetin;2,3-Dihydroquercetin;3,5,7,3',4'-Pentahydroxyflavanone;Dihydroquercetin;Diquertin;Distylin;Lariksin;Lavitol;Taxifolin;Taxifoliol; |
| EINECS: | 207-543-4 |
| Density: | 1.702 g/cm3 |
| Melting Point: | 230-233 °C (dec.) |
| Boiling Point: | 687.6 °C at 760 mmHg |
| Flash Point: | 264.1 °C |
| Appearance: | Yellowish powder |
| Risk Codes: | 22 |
| Safety: | 22-24/25 |
| PSA: | 127.45000 |
| LogP: | 1.18630 |
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(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychroman-4-one
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With hydrogen; palladium on activated charcoal In tetrahydrofuran; methanol at 20℃; for 24h; | 90% |
| With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; methanol for 48h; Inert atmosphere; | 85% |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1.1: K2CO3 / dimethylformamide / 3 h / 130 °C 1.2: 81 percent / NaH / dimethylformamide / 3 h / 20 °C 2.1: 85 percent / Pb3O4 / benzene / 3 h / 75 - 80 °C 3.1: 90 percent / K2CO3 / methanol; tetrahydrofuran / 2 h / 20 °C 4.1: 85 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; MgSO4 / CH2Cl2 / 3 h / 20 °C 5.1: 90 percent / H2 / Pd/C / methanol; tetrahydrofuran / 24 h / 20 °C View Scheme | |
| With extract of Burkholderia oxyphila OX-01, Japan, Tsukuba, acidic forest soil In aq. phosphate buffer at 28℃; for 3h; pH=7; | |
| Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 20 °C / Inert atmosphere 2.2: 20 °C / Inert atmosphere 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; 1,4-dioxane; water / 8 h / 0 - 20 °C / Inert atmosphere 4.1: palladium 10% on activated carbon; hydrogen / methanol; tetrahydrofuran / 48 h / Inert atmosphere View Scheme |
- 1298135-47-3
(2R,3R)-5,7,3',4'-tetrahydroxyflavanonol 2"-acetylrhamnoside
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With sulfuric acid In 1,4-dioxane at 100℃; for 1h; |
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With hydrogenchloride at 55℃; for 0.5h; pH=< 1; | 55% |
- 1235442-81-5
taxifolin O-α-D-glucoside
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With water; Saccharomyces cerevisiae α-glucosidase at 30℃; for 18h; pH=7.3; Enzymatic reaction; Potassium phosphate buffer; |
| Conditions | Yield |
|---|---|
| With extract of Burkholderia oxyphila OX-01, Japan, Tsukuba, acidic forest soil In aq. phosphate buffer at 30℃; for 3h; pH=7; |
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In dichloromethane at 0 - 5℃; for 5h; Large scale; | 41.3 kg |
- 55313-03-6
1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone
- 139-85-5
3,4-dihydroxybenzaldehyde
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| Stage #1: 1-(2',4',6'-trihydroxyphenyl)-2-hydroxyethanone; 3,4-dihydroxybenzaldehyde With rac-Pro-OH In tetrahydrofuran at 85 - 100℃; for 6h; Stage #2: With acetic acid In tetrahydrofuran at 20℃; for 2h; Solvent; Temperature; | 36.7 g |
- 36804-13-4, 91318-14-8, 115523-95-0, 115523-96-1
(-)-chalcone epoxide
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With hydrogenchloride In methanol at 50℃; for 0.333333h; | 82% |
- 480-18-2
taxifolin
| Conditions | Yield |
|---|---|
| With sulfuric acid; water for 2h; Hydrolysis; Heating; | 70% |
| With hesperidinase In water at 37℃; for 36h; | 37 mg |
| With hydrogenchloride; water In methanol at 80℃; for 0.75h; Kinetics; Activation energy; Temperature; Concentration; |
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- 481066-70-0Hydroxyl- and 4-sulfophenyl-modified carbon black. sodium salts
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Chemistry
Molecular Formula: C15H12O7 
Formula Weight: 304.25
IUPAC Name: (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydrochromen-4-one
Synonyms: 2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4h-1-benzopyran-4-on ; (2R-trans)-2-(3,4-dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4-benzopyrone ; Distylin
Melting Point: 230-233°C (dec.)
Flash Point: 264.2 °C
Boiling Point: 687.6 °C at 760 mmHg
Density of Taxifolin (480-18-2): 1.702 g/cm3
Vapour Pressure: 7.51E-20 mmHg at 25°C
Index of Refraction: 1.762
Solubility: Taxifolin (480-18-2) is dissolves in nonpolar solvents (alcohol, acetone, ether), hot water, oil.
Physical State: Taxifolin (480-18-2) is a solid powder.
Color: White to yellowish (Light).
Toxicity Data With Reference
| 1. | mmo-sat 100 µg/plate | ENMUDM Environmental Mutagenesis. 3 (1981),401. | ||
| 2. | mma-sat 1660 nmol/plate | MUREAV Mutation Research. 54 (1978),297. | ||
| 3. | cyt-ham:fbr 1 g/L/48H | MUREAV Mutation Research. 48 (1977),337. | ||
| 4. | ipr-rat LD50:1200 mg/kg | JJPAAZ Japanese Journal of Pharmacology. 21 (1971),377. | ||
| 5. | ipr-mus LD50:985 mg/kg | RPTOAN Russian Pharmacology and Toxicology. Translation of FATOAO. 38 (1975),213. |
Consensus Reports
Reported in EPA TSCA Inventory.
Safety Profile
Moderately toxic by intraperitoneal route. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Risk Statements : 22: Harmful if swallowed
Safety Statements : 22: Do not breathe dust
24/25: Avoid contact with skin and eyes
WGK Germany : 3
RTECS : LK6920000
Specification
Taxifolin (480-18-2) is a white to yellowish solid powder and dissolves in nonpolar solvents (alcohol, acetone, ether), hot water, oil. The product is stable. It should keep tightly closed in dark place and a cool, well-ventilated area.