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Basic Information

Molecular Structure:
CAS No.:	446-72-0
Name:	Genistein
Article Data:	61

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

Synthetic route

: 529-59-9
genistin

: 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions

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

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%

: sulfur trioxide N,N-dimethylformamide complex

: 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions

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

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

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%

...Expand

: 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

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

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%

...Expand

: 15485-65-1
2,4,4',6-tetrahydroxydeoxybenzoin

: 446-72-0
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on

Conditions

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

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℃;

: [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

Conditions	Yield
With sulfatase VIII In water at 37℃; for 0.5h; pH=5.2;	89%

Raw Materials

15485-65-1

152-95-4

98-88-4

541-41-3

68-12-2

156-38-7

2491-38-5

79-03-8

Downstream Products

552-59-0

156-38-7

108-73-6

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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: Irritant 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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