Genistein supplier | CasNO.446-72-0

Name
Genistein
EINECS 207-174-9
CAS No. 446-72-0
Article Data61
CAS DataBase
Density 1.548 g/cm³
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
Appearance Yellow crystalline solid
Safety 26-24/25-22
Risk Codes 36/38
Molecular Structure
Hazard Symbols Xi
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;
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%

: 64-18-6
formic acid

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

: 123-62-6
propionic acid anhydride

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

Conditions

Conditions	Yield
Stage #1: formic acid; propionic acid anhydride at 25 - 45℃; for 2h; Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 20 - 40℃; for 19h; Stage #3: With sulfuric acid; water In acetone at 60℃;	86.5%
Stage #1: formic acid; 2,4,4',6-tetrahydroxydeoxybenzoin; propionic acid anhydride at 25 - 45℃; for 2h; Stage #2: With triethylamine at 20 - 40℃; for 19h; Stage #3: With sulfuric acid; water at 75℃; for 2.5h;	82.5%

...Expand

: 491-80-5
5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on

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

Conditions

Conditions	Yield
With aluminum (III) chloride In toluene at 140℃; for 6h;	84%
With aluminium trichloride In benzene for 18h; Heating;	47%
With hydrogen iodide

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

: 10500-31-9
Propionic formic anhydride

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

Conditions

Conditions	Yield
Stage #1: 2,4,4',6-tetrahydroxydeoxybenzoin; Propionic formic anhydride With triethylamine In acetone at 25 - 40℃; for 3h; Stage #2: With sulfuric acid; water In acetone at 20 - 60℃;	84%

: 51011-05-3
6''-O-malonylgenistin

: 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 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;	82.3%
β-glucosidase, derived from Aspergillus niger In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;	12.1%
diglycosidase, produced by Aspergillus fumigatus IAM2046 In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;	8.2%
β-xylosidase, derived from pectinase G In methanol at 55℃; for 6h; pH=4; Enzyme kinetics; Aqueous acetate buffer;	2%
With Dalbergia nigrescens β-glucosidase In acetate buffer; dimethyl sulfoxide at 37℃; for 0.166667h; pH=5.5; Enzyme kinetics; Further Variations:; Reagents;

: 64-18-6
formic acid

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

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

Conditions

Conditions	Yield
Stage #1: formic acid; 2,4,4',6-tetrahydroxydeoxybenzoin With acetic anhydride; triethylamine at 20℃; for 24h; Industrial scale; Stage #2: With hydrogenchloride; water In methanol at 20℃; for 22h; Industrial scale;	79.5%

: 290-87-9
1,3,5-Triazine

: 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; acetic anhydride In diethyl ether; acetic acid Heating;	78%

: 2491-38-5
2-bromo-1-(4'-hydroxyphenyl)-1-ethanone

: 487-70-7
2,4,6-trihydroxybenzaldehyde

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

Conditions

Conditions	Yield
Stage #1: 2-bromo-1-(4'-hydroxyphenyl)-1-ethanone With thiamine hydrochloride In ethanol at 20℃; for 0.25h; Green chemistry; Stage #2: 2,4,6-trihydroxybenzaldehyde In ethanol at 20℃; for 1.58333h; Green chemistry;	75%

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

: 141-53-7
sodium formate

: 98-88-4
benzoyl chloride

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

Conditions

Conditions	Yield
Stage #1: sodium formate; benzoyl chloride In acetone at 21 - 40℃; for 3h; Stage #2: 2,4,4',6-tetrahydroxydeoxybenzoin With triethylamine In acetone at 21 - 35℃; for 3h; Stage #3: With sulfuric acid; water In acetone at 20℃; for 16h;	52.7%

...Expand

: 22151-32-2
5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid

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

Conditions

Conditions	Yield
at 325℃;

: 78694-77-6
7-((2S,3R,4R)-3,4-Dihydroxy-4-hydroxymethyl-tetrahydro-furan-2-yloxy)-3-[4-((2R,3S,4S)-3,4-dihydroxy-4-hydroxymethyl-tetrahydro-furan-2-yloxy)-phenyl]-5-hydroxy-chromen-4-one

A: 639-97-4, 6477-44-7, 42927-70-8
D-apiose

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

Conditions

Conditions	Yield
With sulfuric acid Heating;

: 78693-95-5
7,4'-di-O-<4-O-β-D-glucopyranosyl-β-D-apiofuranoside> genisteol

A: 639-97-4, 6477-44-7, 42927-70-8
D-apiose

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

C: 50-99-7, 59-23-4, 921-60-8, 1949-88-8, 1990-29-0, 2152-76-3, 2595-97-3, 2595-98-4, 3458-28-4, 4205-23-6, 5934-56-5, 5978-95-0, 5987-68-8, 6027-89-0, 6038-51-3, 7635-11-2, 10030-80-5, 15572-79-9, 19163-87-2, 23567-25-1, 26566-61-0, 30077-17-9, 31103-86-3, 39665-52-6, 40866-07-7, 58367-01-4, 58407-05-9, 58407-06-0, 83198-69-0, 83198-70-3, 83198-71-4, 93780-23-5, 145920-48-5
D-glucose

Conditions

Conditions	Yield
With sulfuric acid In water for 2h; Heating;

...Expand

: 128508-06-5
5-O-β-D-glucopyranosylgenistein

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

Conditions

Conditions	Yield
With malic acid at 60℃; other object of study: half-lives; other reagent : acetic acid, oxalic acid, HCl; other temperature;

: 66026-80-0
4′,7-dihydroxy-8β-D-glucose isoflavone

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

Conditions

Conditions	Yield
With hydrogen iodide; phenol at 135℃; for 7h; Heating;	25 mg

: 32361-88-9
6,8-di-C-β-D-glucopyranosyl-4',5,7-trihydroxyisoflavone

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

Conditions

Conditions	Yield
With hydrogen iodide; phenol Heating;	20 mg

: 148356-61-0
1-(2-acetoxy-4,6-dihydroxyphenyl)-3,3-dimethoxy-2-(4-hydroxyphenyl)propan-1-one

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

Conditions

Conditions	Yield
With hydrogenchloride In methanol for 2h; Heating; Yield given;

: genistein 7-O-(2"-p-coumaroyl-β-D-glucopyranoside)

A: 2280-44-6
D-Glucose

B: 7400-08-0
p-Coumaric Acid

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

Conditions

Conditions	Yield
With hydrogenchloride In methanol Heating;

...Expand

: 152-95-4
sophoricoside

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

Conditions

Conditions	Yield
With water Hydrolysis; Acid hydrolysis;

5.7.4'-trimethoxy-isoflavone: 5.7.4'-trimethoxy-isoflavone

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

Conditions

Conditions	Yield
With hydrogen iodide; acetic anhydride; acetic acid

genisteine-7-methyl ether: genisteine-7-methyl ether

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

Conditions

Conditions	Yield
With hydrogen iodide at 130℃;

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

: 98-09-9
benzenesulfonyl chloride

: 1041727-57-4
3-(4-benzenesulfonyloxyphenyl)-5,7-bis(benzenesulfonyloxy)-4H-chromen-4-one

Conditions

Conditions	Yield
With pyridine at -20℃; for 3h; Inert atmosphere;	99%

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

: 814-68-6
acryloyl chloride

: C21H14O7

Conditions

Conditions	Yield
With triethylamine In acetone at 20℃; for 24h;	98.6%

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

: 108-24-7
acetic anhydride

: 5995-97-1
4',5,7-Triacetoxyisoflavone

Conditions

Conditions	Yield
With pyridine Reflux;	98%
With pyridine at 70℃; for 6h;	96%
With pyridine In chloroform at 20℃; for 8h; Inert atmosphere;	93%
for 6h; Heating;	53%
Acetylation;

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

: 112-76-5
Stearoyl chloride

: genistein-4',7-distearate

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification;	96%

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

: 7,5,4’-trihydroxy-3’-nitroisoflavone

Conditions

Conditions	Yield
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at 20℃; for 1.5h;	96%

: 112-77-6
(Z)-9-octadecenoyl chloride

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

: genistein-4',7-dioleate

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification;	95%

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

: 74-88-4
methyl iodide

: 1162-82-9
4',5,7-trimethoxyisoflavone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 4h;	95%
With potassium carbonate In acetone at 60℃;	95%
With potassium carbonate In acetone at 50℃; for 3h; sonication;	85%

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

: 2106-10-7
1-deoxy-1-fluoro-α-D-glucose

: genistein 7-α-O-glucoside

Conditions

Conditions	Yield
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction;	95%

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

: 108-24-7
acetic anhydride

: 65388-04-7
4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate

Conditions

Conditions	Yield
In pyridine at 20℃; for 24h;	92%
In pyridine at 20℃; for 24h;	92%
With pyridine at 20℃; for 24h;	92%

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

: 142-61-0
Hexanoyl chloride

: 918158-57-3
5,7,4'-tri-O-hexanoyl-genistein

Conditions

Conditions	Yield
With pyridine; dmap	91%
With pyridine; dmap In chloroform at 20℃; for 9h; Inert atmosphere;	91%
With dmap; triethylamine In N,N-dimethyl-formamide at 20℃; for 4.5h; Cooling with ice;	81%
With pyridine at 0 - 20℃; for 18h;

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

A: 21554-71-2
dihydrogenistein

: 124093-22-7
(3S,4R)-3-(4-Hydroxy-phenyl)-chroman-4,5,7-triol

Conditions

Conditions	Yield
With ammonium formate; palladium on activated charcoal In methanol Ambient temperature;	A 90% B n/a
With ammonium formate; palladium on activated charcoal In methanol for 2h; Heating;	A 59% B 21%

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

: 109-64-8
1,3-dibromo-propane

: 862255-04-7
4',5,7-tri(3-bromopropoxy)isoflavone

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1.5h; sonication;	90%
With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 4.75h;

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

: 98-09-9
benzenesulfonyl chloride

: 1041727-51-8
3-(4-hydroxyphenyl)-7-benzenesulfonyloxy-5-hydroxy-4H-chromen-4-one

Conditions

Conditions	Yield
With pyridine In tetrahydrofuran at -20℃; for 0.333333h; Inert atmosphere;	90%

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

: 2052-49-5
tetra(n-butyl)ammonium hydroxide

: tetra n-butylammonium salt of genistein

Conditions

Conditions	Yield
In methanol; water at 20℃;	89%

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

: 106-93-4
ethylene dibromide

: 862255-00-3
7-(2-bromoethoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide sonication;	88%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1.5h; sonication;	86%
With sodium hydrogencarbonate In acetone at 65℃; for 24h;	71%

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

: 108-24-7
acetic anhydride

A: 65388-04-7
4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate

B: 7-acetoxy-4',5-dihydroxygenistein

Conditions

Conditions	Yield
With pyridine for 7h; Reflux;	A 87.2% B 5.3%

...Expand

: 112-77-6
(Z)-9-octadecenoyl chloride

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

: genistein-7-monooleate

Conditions

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification;	87%

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

: 109-64-8
1,3-dibromo-propane

: 862255-02-5
7-(3-bromopropoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide sonication;	87%
With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 1.5h; sonication;	85%
With sodium hydrogencarbonate; potassium carbonate In acetone at 65℃; for 8h;	78.47%

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

: 107-30-2
chloromethyl methyl ether

: 5,7,4'-trimethoxymethoxyisoflavone

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;	87%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;	87%

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: 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

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.

Product Name

Genistein

Synthetic route

Genistein Chemical Properties

Genistein Uses

Genistein Toxicity Data With Reference

Genistein Consensus Reports

Genistein Safety Profile

Genistein Specification

Related Products

Hot Products