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Genistein
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Name

Genistein

 EINECS 207-174-9
CAS No. 446-72-0 Density 1.548 g/cm3
PSA 90.90000 LogP 2.57680
Solubility insoluble in water Melting Point 297-298 °C
Formula C15H10O5 Boiling Point 555.5 °C at 760 mmHg
Molecular Weight 270.241 Flash Point 217.1 °C
Transport Information N/A Appearance Yellow crystalline solid
Safety 26-24/25-22 Risk Codes 36/38
Molecular Structure Molecular Structure of 446-72-0 (Genistein) Hazard Symbols IrritantXi
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;

Article Data 61

Genistein 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%

Genistein Chemical Properties

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

Genistein 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.

Genistein 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.

Genistein Consensus Reports

  Genistein (CAS NO.446-72-0) is reported in EPA TSCA Inventory.

Genistein 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

Genistein 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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