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% |
genistein-7-O-β-D-(6''-O-acetylglucopyranoside)
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% |
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% |
2,4,4',6-tetrahydroxydeoxybenzoin
sodium formate
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% |
2,4,4',6-tetrahydroxydeoxybenzoin
sodium formate
propionyl chloride
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% |
3-(4-hydroxyphenyl)-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride; water In methanol; chloroform for 1h; Reflux; | 92% |
2,4,4',6-tetrahydroxydeoxybenzoin
sodium formate
isobutyryl chloride
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% |
2,4,4',6-tetrahydroxydeoxybenzoin
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 |
2,4,4',6-tetrahydroxydeoxybenzoin
N,N-dimethyl-formamide
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℃; |
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% |
formic acid
2,4,4',6-tetrahydroxydeoxybenzoin
propionic acid anhydride
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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% |
5,7-Dihydroxy-3-(4-methoxy-phenyl)-chromen-4-on
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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 |
2,4,4',6-tetrahydroxydeoxybenzoin
Propionic formic anhydride
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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% |
6''-O-malonylgenistin
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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; |
formic acid
2,4,4',6-tetrahydroxydeoxybenzoin
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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% |
1,3,5-Triazine
2,4,4',6-tetrahydroxydeoxybenzoin
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate; acetic anhydride In diethyl ether; acetic acid Heating; | 78% |
2-bromo-1-(4'-hydroxyphenyl)-1-ethanone
2,4,6-trihydroxybenzaldehyde
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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% |
2,4,4',6-tetrahydroxydeoxybenzoin
sodium formate
benzoyl chloride
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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% |
5,7-dihydroxy-3-(4-hydroxy-phenyl)-4-oxo-4H-chromene-2-carboxylic acid
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
at 325℃; |
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
D-apiose
B
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With sulfuric acid Heating; |
7,4'-di-O-<4-O-β-D-glucopyranosyl-β-D-apiofuranoside> genisteol
A
D-apiose
B
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
C
D-glucose
Conditions | Yield |
---|---|
With sulfuric acid In water for 2h; Heating; |
5-O-β-D-glucopyranosylgenistein
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With malic acid at 60℃; other object of study: half-lives; other reagent : acetic acid, oxalic acid, HCl; other temperature; |
4′,7-dihydroxy-8β-D-glucose isoflavone
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide; phenol at 135℃; for 7h; Heating; | 25 mg |
6,8-di-C-β-D-glucopyranosyl-4',5,7-trihydroxyisoflavone
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide; phenol Heating; | 20 mg |
1-(2-acetoxy-4,6-dihydroxyphenyl)-3,3-dimethoxy-2-(4-hydroxyphenyl)propan-1-one
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride In methanol for 2h; Heating; Yield given; |
A
D-Glucose
B
p-Coumaric Acid
C
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogenchloride In methanol Heating; |
Conditions | Yield |
---|---|
With water Hydrolysis; Acid hydrolysis; |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide; acetic anhydride; acetic acid |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With hydrogen iodide at 130℃; |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
benzenesulfonyl chloride
3-(4-benzenesulfonyloxyphenyl)-5,7-bis(benzenesulfonyloxy)-4H-chromen-4-one
Conditions | Yield |
---|---|
With pyridine at -20℃; for 3h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With triethylamine In acetone at 20℃; for 24h; | 98.6% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
acetic anhydride
4',5,7-Triacetoxyisoflavone
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; |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification; | 96% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Conditions | Yield |
---|---|
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at 20℃; for 1.5h; | 96% |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification; | 95% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
methyl iodide
4',5,7-trimethoxyisoflavone
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% |
Conditions | Yield |
---|---|
With α-glucosidase from sulfolobus solfataricus In dimethyl sulfoxide at 45℃; for 2h; pH=9; Enzymatic reaction; | 95% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
acetic anhydride
4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate
Conditions | Yield |
---|---|
In pyridine at 20℃; for 24h; | 92% |
In pyridine at 20℃; for 24h; | 92% |
With pyridine at 20℃; for 24h; | 92% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
Hexanoyl chloride
5,7,4'-tri-O-hexanoyl-genistein
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; |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
A
dihydrogenistein
(3S,4R)-3-(4-Hydroxy-phenyl)-chroman-4,5,7-triol
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% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
1,3-dibromo-propane
4',5,7-tri(3-bromopropoxy)isoflavone
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; |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
benzenesulfonyl chloride
3-(4-hydroxyphenyl)-7-benzenesulfonyloxy-5-hydroxy-4H-chromen-4-one
Conditions | Yield |
---|---|
With pyridine In tetrahydrofuran at -20℃; for 0.333333h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
In methanol; water at 20℃; | 89% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
ethylene dibromide
7-(2-bromoethoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
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% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
acetic anhydride
A
4-(7-acetoxy-5-hydroxy-4-oxo-4H-chromen-3-yl)phenyl acetate
Conditions | Yield |
---|---|
With pyridine for 7h; Reflux; | A 87.2% B 5.3% |
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide at 30℃; for 2.5h; Etherification; | 87% |
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
1,3-dibromo-propane
7-(3-bromopropoxy)-5-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
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% |
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% |
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 (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.
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 (CAS NO.446-72-0) is reported in EPA TSCA Inventory.
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
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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