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446-72-0

Basic Information
CAS No.: 446-72-0
Name: Genistein
Article Data: 61
Cas Database
Molecular Structure:
Molecular Structure of 446-72-0 (Genistein)
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: IrritantXi
Risk Codes: 36/38
Safety: 26-24/25-22
Transport Information: N/A
PSA: 90.90000
LogP: 2.57680
Synthetic route
529-59-9

genistin

446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;100%
In hydrogenchloride99%
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
ConditionsYield
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%

sulfur trioxide N,N-dimethylformamide complex

446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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℃;

[5-hydroxy-3-(4-hydroxyphenyl)-4-oxochromen-7-yl]dihydrogen phosphate

446-72-0

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions
ConditionsYield
With sulfatase VIII In water at 37℃; for 0.5h; pH=5.2;89%
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  • Genistein    CAS: 446-72-0

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    Genistein CAS: 446-72-0

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Chemistry

Molecular Structure of Genistein (CAS NO.446-72-0):

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: IrritantXi
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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