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446-72-0

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446-72-0 Usage

Chemical Description

Genistein and orobol are isoflavone bis-C-glycosides, while p-TsOH·H2O is para-toluenesulfonic acid monohydrate, Na2S2O3 is sodium thiosulfate, CHCl3 is chloroform, MeOH is methanol, and silica gel is a type of stationary phase used in column chromatography.

Check Digit Verification of cas no

The CAS Registry Mumber 446-72-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,4 and 6 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 446-72:
(5*4)+(4*4)+(3*6)+(2*7)+(1*2)=70
70 % 10 = 0
So 446-72-0 is a valid CAS Registry Number.
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

446-72-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (G0272)  Genistein  >98.0%(HPLC)

  • 446-72-0

  • 100mg

  • 122.00CNY

  • Detail
  • TCI America

  • (G0272)  Genistein  >98.0%(HPLC)

  • 446-72-0

  • 1g

  • 330.00CNY

  • Detail
  • USP

  • (1288816)  Genistein  United States Pharmacopeia (USP) Reference Standard

  • 446-72-0

  • 1288816-15MG

  • 4,662.45CNY

  • Detail
  • Sigma-Aldrich

  • (92136)  Genistein  analytical standard

  • 446-72-0

  • 92136-10MG

  • 1,964.43CNY

  • Detail
  • Sigma-Aldrich

  • (05360590)  Genistein  primary pharmaceutical reference standard

  • 446-72-0

  • 05360590-50MG

  • 5,933.07CNY

  • Detail
  • Sigma

  • (G6649)  Genistein  synthetic, ≥98% (HPLC), powder

  • 446-72-0

  • G6649-5MG

  • 402.48CNY

  • Detail
  • Sigma

  • (G6649)  Genistein  synthetic, ≥98% (HPLC), powder

  • 446-72-0

  • G6649-25MG

  • 1,193.40CNY

  • Detail
  • Sigma

  • (G6649)  Genistein  synthetic, ≥98% (HPLC), powder

  • 446-72-0

  • G6649-100MG

  • 3,616.47CNY

  • Detail
  • Sigma

  • (G6776)  Genistein  from Glycine max (soybean), ~98% (HPLC)

  • 446-72-0

  • G6776-5MG

  • 752.31CNY

  • Detail
  • Sigma

  • (G6776)  Genistein  from Glycine max (soybean), ~98% (HPLC)

  • 446-72-0

  • G6776-10MG

  • 1,301.04CNY

  • Detail

446-72-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name Genistein

1.2 Other means of identification

Product number -
Other names 5,7,4'-trihydroxyisoflavone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:446-72-0 SDS

446-72-0Synthetic route

genistin
529-59-9

genistin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
genistein-7-O-β-D-(6''-O-acetylglucopyranoside)
73566-30-0

genistein-7-O-β-D-(6''-O-acetylglucopyranoside)

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

sulfur trioxide N,N-dimethylformamide complex

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

propionyl chloride
79-03-8

propionyl chloride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
3-(4-hydroxyphenyl)-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one
1236208-91-5

3-(4-hydroxyphenyl)-5,7-bis(methoxymethoxy)-4H-1-benzopyran-4-one

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

isobutyryl chloride
79-30-1

isobutyryl chloride

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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
2,4,4',6-tetrahydroxydeoxybenzoin
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

N,N-dimethyl-formamide
68-12-2, 33513-42-7

N,N-dimethyl-formamide

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

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

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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%
formic acid
64-18-6

formic acid

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

2,4,4',6-tetrahydroxydeoxybenzoin

propionic acid anhydride
123-62-6

propionic acid anhydride

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

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

Conditions
ConditionsYield
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
491-80-5

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

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

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

Conditions
ConditionsYield
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
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

Propionic formic anhydride
10500-31-9

Propionic formic anhydride

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

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

Conditions
ConditionsYield
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
51011-05-3

6''-O-malonylgenistin

5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
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 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
64-18-6

formic acid

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

2,4,4',6-tetrahydroxydeoxybenzoin

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

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

Conditions
ConditionsYield
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
290-87-9

1,3,5-Triazine

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

2,4,4',6-tetrahydroxydeoxybenzoin

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

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

Conditions
ConditionsYield
With boron trifluoride diethyl etherate; acetic anhydride In diethyl ether; acetic acid Heating;78%
2-bromo-1-(4'-hydroxyphenyl)-1-ethanone
2491-38-5

2-bromo-1-(4'-hydroxyphenyl)-1-ethanone

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

2,4,6-trihydroxybenzaldehyde

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

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

Conditions
ConditionsYield
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
15485-65-1

2,4,4',6-tetrahydroxydeoxybenzoin

sodium formate
141-53-7

sodium formate

benzoyl chloride
98-88-4

benzoyl chloride

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

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

Conditions
ConditionsYield
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
22151-32-2

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

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

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

Conditions
ConditionsYield
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
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

B

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

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

Conditions
ConditionsYield
With sulfuric acid Heating;
5-O-β-D-glucopyranosylgenistein
128508-06-5

5-O-β-D-glucopyranosylgenistein

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

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

Conditions
ConditionsYield
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
66026-80-0

4′,7-dihydroxy-8β-D-glucose isoflavone

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

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

Conditions
ConditionsYield
With hydrogen iodide; phenol at 135℃; for 7h; Heating;25 mg
6,8-di-C-β-D-glucopyranosyl-4',5,7-trihydroxyisoflavone
32361-88-9

6,8-di-C-β-D-glucopyranosyl-4',5,7-trihydroxyisoflavone

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

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

Conditions
ConditionsYield
With hydrogen iodide; phenol Heating;20 mg
1-(2-acetoxy-4,6-dihydroxyphenyl)-3,3-dimethoxy-2-(4-hydroxyphenyl)propan-1-one
148356-61-0

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
446-72-0

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

Conditions
ConditionsYield
With hydrogenchloride In methanol for 2h; Heating; Yield given;
genistein 7-O-(2

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

A

D-Glucose
2280-44-6

D-Glucose

B

p-Coumaric Acid
7400-08-0

p-Coumaric Acid

C

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

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

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;
sophoricoside
152-95-4

sophoricoside

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

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

Conditions
ConditionsYield
With water Hydrolysis; Acid hydrolysis;
5.7.4'-trimethoxy-isoflavone

5.7.4'-trimethoxy-isoflavone

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

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

Conditions
ConditionsYield
With hydrogen iodide; acetic anhydride; acetic acid
genisteine-7-methyl ether

genisteine-7-methyl ether

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

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

Conditions
ConditionsYield
With hydrogen iodide at 130℃;
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

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

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

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

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

Conditions
ConditionsYield
With pyridine at -20℃; for 3h; Inert atmosphere;99%
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

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

acryloyl chloride
814-68-6

acryloyl chloride

C21H14O7

C21H14O7

Conditions
ConditionsYield
With triethylamine In acetone at 20℃; for 24h;98.6%
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

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

acetic anhydride
108-24-7

acetic anhydride

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

4',5,7-Triacetoxyisoflavone

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

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

Stearoyl chloride
112-76-5

Stearoyl chloride

genistein-4',7-distearate

genistein-4',7-distearate

Conditions
ConditionsYield
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
446-72-0

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

7,5,4’-trihydroxy-3’-nitroisoflavone

7,5,4’-trihydroxy-3’-nitroisoflavone

Conditions
ConditionsYield
With ammonium nitrate; trifluoroacetic anhydride In acetonitrile at 20℃; for 1.5h;96%
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

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

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

genistein-4',7-dioleate

genistein-4',7-dioleate

Conditions
ConditionsYield
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
446-72-0

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

methyl iodide
74-88-4

methyl iodide

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

4',5,7-trimethoxyisoflavone

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

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

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

1-deoxy-1-fluoro-α-D-glucose

genistein 7-α-O-glucoside

genistein 7-α-O-glucoside

Conditions
ConditionsYield
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
446-72-0

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

acetic anhydride
108-24-7

acetic anhydride

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

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

Conditions
ConditionsYield
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
446-72-0

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

Hexanoyl chloride
142-61-0

Hexanoyl chloride

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

5,7,4'-tri-O-hexanoyl-genistein

Conditions
ConditionsYield
With pyridine; dmap91%
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
446-72-0

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

A

dihydrogenistein
21554-71-2

dihydrogenistein

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

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

Conditions
ConditionsYield
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
446-72-0

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

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

1,3-dibromo-propane

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

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

Conditions
ConditionsYield
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
446-72-0

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

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

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

3-(4-hydroxyphenyl)-7-benzenesulfonyloxy-5-hydroxy-4H-chromen-4-one

Conditions
ConditionsYield
With pyridine In tetrahydrofuran at -20℃; for 0.333333h; Inert atmosphere;90%
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

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

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

tetra(n-butyl)ammonium hydroxide

tetra n-butylammonium salt of genistein

tetra n-butylammonium salt of genistein

Conditions
ConditionsYield
In methanol; water at 20℃;89%
5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on
446-72-0

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

ethylene dibromide
106-93-4

ethylene dibromide

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

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

Conditions
ConditionsYield
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
446-72-0

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

acetic anhydride
108-24-7

acetic anhydride

A

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

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

B

7-acetoxy-4',5-dihydroxygenistein

7-acetoxy-4',5-dihydroxygenistein

Conditions
ConditionsYield
With pyridine for 7h; Reflux;A 87.2%
B 5.3%
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

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

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

genistein-7-monooleate

genistein-7-monooleate

Conditions
ConditionsYield
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
446-72-0

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

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

1,3-dibromo-propane

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

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

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

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

chloromethyl methyl ether
107-30-2

chloromethyl methyl ether

5,7,4'-trimethoxymethoxyisoflavone

5,7,4'-trimethoxymethoxyisoflavone

Conditions
ConditionsYield
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%

446-72-0Relevant articles and documents

Hydrolysis of soybean isoflavonoid glycosides by Dalbergia β-glucosidases

Chuankhayan, Phimonphan,Rimlumduan, Thipwarin,Svasti, Jisnuson,Ketudat Cairns, James R.

, p. 2407 - 2412 (2007)

Two β-glucosidases from the legumes Dalbergia cochinchinensis and Dalbergia nigrescens were compared for their ability to hydrolyze isoflavonoid glycosides from soybean. Both D. nigrescens and D. cochinchinensis β-glucosidases could hydrolyze conjugated soybean glycosides, but D. nigrescens β-glucosidase hydrolyzed both conjugated and nonconjugated glycosides in crude soybean extract more rapidly. The kinetic properties K m, kcat, and kcat/Km of the Dalbergia β-glucosidases toward conjugated isoflavonoid glycosides, determined using high-performance liquid chromatography, confirmed the higher efficiency of the D. nigrescens β-glucosidase in hydrolyzing these substrates. The D. nigrescens β-glucosidase could also efficiently hydrolyze isoflavone glycosides in soy flour suspensions, suggesting its application to increase free isoflavones in soy products.

Deglycosylation of isoflavonoid glycosides from maackia amurensis cell culture by β-D-glucosidase from littorina sitkana hepatopancrease

Kusaikin,Zakharenko,Ermakova,Veselova,Grigoruk,Fedoreev,Zvyagintseva

, p. 197 - 200 (2011)

Maakia amurensis (strain A-18) cell culture synthesizes a significant quantity of isoflavonoids, a large part of which consists of isoflavone glucosides and malonylglucosides. β-D-Hydrolase enzyme complexes from the marine mollusk Littorina sitkana and the marine mycelial fungus P. canescens were used to obtain isoflavones from their conjugated forms. The specificity of β-D-glucanases from L. sitkana for various glycosides was studied. The deglycosylation efficiency depended on the aglycon structure. The deglycosylated fraction of isoflavonoids obtained from M. amurensis cell culture exhibited antitumor activity.

-

Kathsev,Nikonov

, (1972)

-

-

Zapesochnaya,Laman

, (1977)

-

First finding of Daidzein 7-O-phosphate and Genistein 7-O-phosphate that are hydrolyzed by sulfatase

Kanakubo, Akira,Koga, Kazushi,Isobe, Minoru,Fushimi, Tatsushi,Saitoh, Takanobu,Ohshima, Yoshifumi,Tsukamoto, Yoshinori

, p. 8801 - 8805 (2001)

Attempted structural assignment of two water soluble isoflavone analogs of Daidzein and Genistein, was initially assumed to be the corresponding sulfates on the basis of the facts that these analogs were hydrolyzed by sulfatase; however, they were eventua

Continuous flow microchannel synthesis process of flavonoid compounds

-

Paragraph 0050-0059; 0061, (2021/06/22)

The invention provides a continuous flow microchannel synthesis process of flavonoid compounds. According to the process, hesperidin and iodine elementary substance are used as raw materials and react in a continuous flow microchannel reactor in the presence of a reaction solvent to synthesize the flavonoid compound as shown in a formula A. Compared with a traditional kettle-type preparation process, the process disclosed by the invention has the advantages that the preparation time is obviously shortened, and the conversion rate of raw materials and the yield of products are obviously improved; and especially, when the diosmin is prepared under optimal process conditions of continuous flow microchannel synthesis, the conversion rate of the raw material hesperidin is as high as 96.48%, and the yield of the product diosmin is as high as 81.96%. The continuous flow micro-channel synthesis process provided by the invention is beneficial to realizing safe, efficient and rapid industrial production of flavonoid compounds, and has a wide application prospect.

Synthesis, Characterization, and Antioxidant Activities of Genistein, Biochanin A, and Their Analogues

Hamza Sherif, Salah,Gebreyohannes, BerihuTekluu

, (2018/04/30)

A series of naturally occurring genistein (3) and biochanin A (4) compounds and their analogues were synthesized from phloroglucinol. The structures of all the synthesized compounds were established by the combined use of 1HNMR, 13CNMR, IR spectral data, and mass spectrometry; their antioxidant activities were investigated. Most of the synthesized compounds show moderate-to-high activity; only two compounds exhibit no significant activity.

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