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| CAS No.: | 446-72-0 |
|---|---|
| Name: | Genistein |
| Article Data: | 61 |
| Molecular Structure: | |
|
|
|
| Formula: | C15H10O5 |
| Molecular Weight: | 270.241 |
| Synonyms: | 4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3- (4-hydroxyphenyl)-;5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one;5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one;Prunetol;Isoflavone, 4,5,7-trihydroxy-;4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-;SIPI 807-1;5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone;5-18-04-00594 (Beilstein Handbook Reference);C.I. 75610;NPI 031L;4,5,7-Trihydroxyisoflavone;4',5,7-trihydroxyisoflavone;4,5, 7-Trihydroxyisoflavone;Genisteol;Baichanin A;Differenol A;4H-1-Benzopyran-4-one,5,7-dihydroxy-3- (4-hydroxyphenyl)-;Genisterin;Sophoricol;5,7,4-Trihydroxyisoflavone;Genistein 4,5,7-Trihydroxyisoflavone; |
| EINECS: | 207-174-9 |
| Density: | 1.548 g/cm3 |
| Melting Point: | 297-298 °C |
| Boiling Point: | 555.5 °C at 760 mmHg |
| Flash Point: | 217.1 °C |
| Solubility: | insoluble in water |
| Appearance: | Yellow crystalline solid |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/38 |
| Safety: | 26-24/25-22 |
| PSA: | 90.90000 |
| LogP: | 2.57680 |
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| Conditions | Yield |
|---|---|
| β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 100% |
| In hydrogenchloride | 99% |
| β-glucosidase, derived from almond In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 11.8% |
- 73566-30-0
genistein-7-O-β-D-(6''-O-acetylglucopyranoside)
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| diglycosidase, produced by Penicillium multicolor IAM7153 In methanol at 55℃; for 3h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 99.9% |
| diglycosidase, produced by Aspergillus fumigatus IAM2046 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 35.2% |
| β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 6.2% |
| β-xylosidase, derived from pectinase G In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer; | 0.5% |
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin With sodium carbonate In N,N-dimethyl-formamide at 25℃; for 3h; Stage #2: sulfur trioxide N,N-dimethylformamide complex In N,N-dimethyl-formamide at 0 - 80℃; for 18.5h; Stage #3: With sulfuric acid; water In N,N-dimethyl-formamide for 0.666667h; Product distribution / selectivity; | 95% |
- 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin
- 141-53-7
sodium formate
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With propionyl chloride In acetone at 21 - 32℃; for 1h; Stage #2: With triethylamine In acetone at 20 - 32℃; for 2.5h; Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity; | 94.8% |
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With acetyl chloride In acetone at 12 - 25℃; for 2h; Stage #2: With triethylamine In acetone at 18 - 32℃; for 3h; Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity; | 91.7% |
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate With isobutyryl chloride In acetone at 21 - 32℃; for 2h; Stage #2: With triethylamine In acetone at 18 - 32℃; for 2.5h; Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; Product distribution / selectivity; | 90.2% |
- 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin
- 141-53-7
sodium formate
- 79-03-8
propionyl chloride
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| Stage #1: sodium formate; propionyl chloride In acetone at 21 - 35℃; for 3h; Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 20 - 22℃; for 2h; Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h; | 93% |
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; propionyl chloride In acetone at 21 - 35℃; for 2h; Stage #2: With triethylamine In acetone at 18 - 35℃; for 3h; Stage #3: With sulfuric acid; water In acetone at 60 - 70℃; for 1.5h; | 92.2% |
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; propionyl chloride In formic acid ethyl ester at 23 - 35℃; for 3h; Stage #2: With triethylamine In formic acid ethyl ester at 18 - 22℃; for 16h; Stage #3: With sulfuric acid; water In formic acid ethyl ester at 80℃; | 92.7% |
- 1236208-91-5
3-(4-hydroxyphenyl)-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| With hydrogenchloride; water In methanol; chloroform for 1h; Reflux; | 92% |
- 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin
- 141-53-7
sodium formate
- 79-30-1
isobutyryl chloride
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; sodium formate; isobutyryl chloride In acetone at 21 - 32℃; for 3h; Stage #2: With triethylamine In acetone at 18 - 32℃; for 2h; Stage #3: With sulfuric acid; water In acetone at 60 - 70℃; for 3h; | 90.3% |
- 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| With boron trifluoride diethyl etherate; methanesulfonyl chloride In N,N-dimethyl-formamide at 50℃; for 12h; Molecular sieve; | 90% |
| With methanesulfonyl chloride In N,N-dimethyl-formamide at 60 - 70℃; for 1h; | 53% |
| Multi-step reaction with 2 steps 1: pyridine / Behandeln des Reaktionsprodukts mit wss. Natronlauge 2: 325 °C View Scheme |
- 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin
- 68-12-2, 33513-42-7
N,N-dimethyl-formamide
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| Stage #1: N,N-dimethyl-formamide With phosphorus pentachloride at 55℃; for 0.333333h; Chlorination; Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 20℃; for 1h; Cycloaddition; | 90% |
| Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin With boron trifluoride diethyl etherate In N,N-dimethyl-formamide at 50 - 60℃; Cooling with ice; Stage #2: N,N-dimethyl-formamide With methanesulfonyl chloride at 50 - 70℃; | 84% |
| With boron trifluoride diethyl etherate; methanesulfonyl chloride 1.) irradiation, reflux, 15 s, 2.) irradiation, reflux, 1 min; Yield given. Multistep reaction; | |
| With phosphorus pentachloride; boron trifluoride diethyl etherate at 20℃; for 1h; Cyclization; | |
| With boron trifluoride diethyl etherate; methanesulfonyl chloride at 50 - 100℃; |
- 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
| Conditions | Yield |
|---|---|
| With sulfatase VIII In water at 37℃; for 0.5h; pH=5.2; | 89% |
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Chemistry
Molecular Structure of Genistein (CAS NO.446-72-0):
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IUPAC Name: 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one
Empirical Formula: C15H10O5
Molecular Weight: 270.2369
H bond acceptors: 5
H bond donors: 3
Freely Rotating Bonds: 4
Polar Surface Area: 86.99 Å2
Index of Refraction: 1.732
Molar Refractivity: 69.85 cm3
Molar Volume: 174.5 cm3
Surface Tension: 79.5 dyne/cm
Density: 1.548 g/cm3
Flash Point: 217.1 °C
Enthalpy of Vaporization: 86.81 kJ/mol
Boiling Point: 555.5 °C at 760 mmHg
Vapour Pressure: 6E-13 mmHg at 25°C
Melting point: 297-298 °C
Storage temp: −20°C
Water Solubility: insoluble
Merck: 14,4391
BRN: 263823
InChI
InChI=1/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
Smiles
c12c(c(c(c3ccc(O)cc3)co1)=O)c(cc(c2)O)O
EINECS: 207-174-9
Product Categories: pharmacetical; Biochemistry; Flavonoids; Natural Plant Extract; The group of Daidzin; Inhibitors; Tyrosine Kinase Inhibitors; Protein Kinase; Signalling
Synonyms: 4H-1-Benzopyran-4-one, 5, 7-dihydroxy-3- (4-hydroxyphenyl)- ; 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one ; 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one ; Isoflavone, 4,5,7-trihydroxy- ; 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4-benzopyrone ; 5-18-04-00594 (Beilstein Handbook Reference) ; 4,5,7-Trihydroxyisoflavone
Uses
Genistein (CAS NO.446-72-0) exhibits specific inhibitory activity against tyrosine kinases, including autophosphorylation of epidermal growth factor receptor kinase (IC50 - 2.6uM). Also inhibits other protein kinases through competitive inhibition of ATP. Inhibits tumor cell.
Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| mouse | LD | intraperitoneal | > 500mg/kg (500mg/kg) | Journal of Antibiotics. Vol. 39, Pg. 606, 1986. |
Consensus Reports
Genistein (CAS NO.446-72-0) is reported in EPA TSCA Inventory.
Safety Profile
Hazard Codes: 
Xi
Risk Statements: 36/38
R36/38:Irritating to eyes and skin.
Safety Statements: 26-24/25-22
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S24/25:Avoid contact with skin and eyes.
S22:Do not breathe dust.
WGK Germany: 3
RTECS: NR2392000
Specification
Biological effects of Genistein (CAS NO.446-72-0) are some isoflavones act as antioxidants to counteract damaging effects of free radicals in tissues; Genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis and it makes some cells more sensitive to radio-therapy.
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