ChemicalBook > CAS DataBase List > 5,7-Dihydrox -4'-methoxyisoflavone

5,7-Dihydrox -4'-methoxyisoflavone

Product Name
5,7-Dihydrox -4'-methoxyisoflavone
CAS No.
491-80-5
Chemical Name
5,7-Dihydrox -4'-methoxyisoflavone
Synonyms
BIOCHANIN A;BIOCHANIN;BIOCHANIN A (AHP);OlMelin;Pratensol;Bilchanin A;Biochani,Olmelin;5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one;5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one;NSC 123538
CBNumber
CB8474490
Molecular Formula
C16H12O5
Formula Weight
284.26
MOL File
491-80-5.mol
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5,7-Dihydrox -4'-methoxyisoflavone Property

Melting point:
210-213 °C(lit.)
Boiling point:
340-355 °C(Press: 0.5 Torr)
Density 
1.420±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
acetone: 10 mg/mL, clear, brown
form 
Powder
pka
6.50±0.20(Predicted)
color 
Off-White to Beige
Water Solubility 
Soluble in water (<1 mg/ml at 25°C), chloroform, methanol, DMSO (57 mg/ml at 25°C), and ethanol (9 mg/ml at 25°C).
λmax
263nm(EtOH)(lit.)
BRN 
278107
LogP
3.341 (est)
CAS DataBase Reference
491-80-5(CAS DataBase Reference)
EPA Substance Registry System
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- (491-80-5)
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Safety

Safety Statements 
22-24/25
WGK Germany 
3
RTECS 
DJ3002500
F 
10
TSCA 
Yes
HS Code 
29329990
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHL80012
Product name
Biochanin A
Purity
phyproof? Reference Substance
Packaging
25MG
Price
$259
Updated
2024/03/01
Sigma-Aldrich
Product number
92142
Product name
Biochanin A
Purity
analytical standard
Packaging
50mg
Price
$183
Updated
2024/03/01
Sigma-Aldrich
Product number
1071381
Product name
Biochanin A
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
20mg
Price
$344
Updated
2024/03/01
TCI Chemical
Product number
B4098
Product name
Biochanin A
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$217
Updated
2024/03/01
TCI Chemical
Product number
B4098
Product name
Biochanin A
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$728
Updated
2024/03/01
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5,7-Dihydrox -4'-methoxyisoflavone Chemical Properties,Usage,Production

Description

Biochanin A is a natural isoflavone with diverse biological actions, most notably as a phytoestrogen. It can affect hormone levels by inhibiting 5α-reductase and 17β-hydroxysteroid dehydrogenase or altering aromatase (CYP19A1) activity. Also known as 4’-methyl genistein, biochanin A can be metabolized in vivo to genistein , another phytoestrogen with diverse effects. Biochanin A also intersects with signaling through peroxisome proliferator-activated receptors (PPARs), as it activates PPARγ (EC50 = 19 μM) and has also been shown to activate a PPARα promoter. Moreover, it increases the expression of the PPARγ coactivator PGC-1α, promoting mitochondrial biogenesis. Biochanin A also inhibits fatty acid amide hydrolase (IC50 = 2.4 μM) and acts as an agonist of the aryl hydrocarbon receptor (EC50 = 0.25 μM).

Chemical Properties

Off-White Solid

Uses

phytoestrogen

Uses

It has putative benefits in dietary cancer prophylaxis. It has also been found to inhibit fatty acid amide hydrolase and to act as agonist of PPARgamma, nuclear receptor that is current pharmacological target for the treatment of diabetes type 2. It acts as an antineoplastic agent. It is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects. It is a nitric oxide synthase inhibitor and apoptosis inducer

Uses

An isoflavone with anticancer proliferation, differentiation and chemopreventitive properties. Inhibits metabolic activation of benzo[a]pyrene

Definition

ChEBI: Biochanin A is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone which is substituted by an additional hydroxy group at position 5 and a methoxy group at position 4'. A phytoestrogen, it has putative benefits in dietary cancer prophylaxis. It has a role as a phytoestrogen, a plant metabolite, an EC 3.5.1.99 (fatty acid amide hydrolase) inhibitor, a tyrosine kinase inhibitor and an antineoplastic agent. It is a member of 7-hydroxyisoflavones and a member of 4'-methoxyisoflavones. It is a conjugate acid of a biochanin A(1-).

General Description

Biochanin A (BCA) is synthesized in vitro from phloroglucinol. A series of steps involving Friedel?Crafts reaction results in an intermediate product 1-(2,4,6-trihydroxyphenyl)-2-(4 methoxyphenyl) ethanone, which post cyclization leads to BCA. It is catabolized to isoflavone genistein post ingestion.

Biochem/physiol Actions

Biochanin A is an isoflavone phytoestrogen found in red clover (Trifolium pratense) that is a selective agonist at ER-β estrogen receptors, and may have chemopreventive efficacy against breast cancer. In line with its low activity at ER-α estrogen receptors, it is essentially devoid of uterotrophic activity. Biochanin A is also a ligand for the aryl hydrocarbon receptor (AhR). It reduces arterial resistance and enhances microcirculation perhaps via effects on potassium and/or calcium ion channels. Induction of sulfotransferases for xenobiotic detoxification has been proposed as a mechanism of its cancer preventive effects.

5,7-Dihydrox -4'-methoxyisoflavone Preparation Products And Raw materials

Raw materials

Preparation Products

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5,7-Dihydrox -4'-methoxyisoflavone Suppliers

Americas 1 Australia 1 Belgium 1 Canada 1 China 304 Czech Republic 1 Europe 1 France 2 Germany 4 India 8 Japan 3 Switzerland 1 United Kingdom 8 United States 42 Global 378
Portail Substances Chimiques
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Fax
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Email
webmestre-substances@ineris.fr
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France
ProdList
6024
Advantage
58
Extrasynthese
Tel
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Fax
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Email
info@extrasynthese.com
Country
France
ProdList
1333
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View Lastest Price from 5,7-Dihydrox -4'-methoxyisoflavone manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
5,7-Dihydrox -4'-methoxyisoflavone 491-80-5
Price
US $1.00-100.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
4000KG
Release date
2024-07-08
PNP Biotech Co. Ltd
Product
5,7-Dihydrox -4'-methoxyisoflavone 491-80-5
Price
US $0.00/kg
Min. Order
25kg
Purity
HPLC>99%
Supply Ability
Inquiry
Release date
2022-09-16
Shanghai Standard Technology Co., Ltd.
Product
Biochanin A 491-80-5
Price
US $0.00/mg
Min. Order
5mg
Purity
≥98%(HPLC)
Supply Ability
10 g
Release date
2019-10-25

491-80-5, 5,7-Dihydrox -4'-methoxyisoflavoneRelated Search:

p-Anisidine Riboflavin Genistein Theaflavin 1-Hydroxyethylidene-1,1-diphosphonic acid Riboflavin 5'-Monophosphate Sodium Salt Anisole Bensulfuron methyl Kresoxim-methyl Methylparaben Aloe emodin p-Anisaldehyde Emodin Triclosan Thiophanate-methyl Methyl acrylate Curcumin (Trifluoromethoxy)benzene

  • Biochani,Olmelin
  • 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one
  • BIOCHANIN A (AHP)
  • BIOCHANIN
  • 5,7-DIHYDROXY-4''-METHOXYISOFLAVONE, 98% BIOCHANIN A
  • 5,7-Dihydrox -4'-methoxyisoflavone
  • 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  • Biochanin A, (5,7-Dihydroxy-4’-methoxyisoflavone)
  • Biochanin A，Genistein 4'-methyl ether，5,7-Dihydrox -4'-methoxyisoflavone
  • 3-(4-Methoxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 4'-Methylgenistein
  • Bilchanin A
  • NSC 123538
  • Biochanin A (4-Methylgenistein)
  • OlMelin
  • Pratensol
  • Biochanin A,5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether
  • 5,7-Dihydrox -4'-methoxyisoflavone 491-80-5
  • 7-hydroxy-3-(4-methoxyphenyl)-4-oxo-1-benzopyran-5-olate
  • 5,7-dihydroxy-3-(4-methoxyphenyl)-4h-1-benzopyran-4-on
  • 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-1-Benzopyran-4-one
  • APIGENIN 4-METHYL ETHER
  • BIOCHANIN A
  • 5,7-DIHYDROXY-4'-METHOXYISOFLAVONE
  • 5,7-DIHYDROXY-4-METHOXYISOFLAVONE
  • Genistein 4′-methyl ether
  • 5,7-dihydroxy-3-p-methoxyphenyl-4H-chromen-4-one
  • 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)-
  • 5,7-Dihydroxy-4'-methoxyisoflavone Genistein 4'-methyl ether 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
  • Biochanin A &gt
  • Genistein Methyl Ether
  • Chickpea bud A
  • 5,7-Dihydroxy-4'-methoxyisoflavone (Biochanin A)
  • TIANFUCHEM--High purity 491-80-5 5,7-Dihydrox -4'-methoxyisoflavone
  • Chickpea sproutin A
  • Chickpea A
  • 5,7- Dihydroxy - 4'- methoxy Isoflovone (or) Biochanin-A
  • Chickpea sprout extract
  • Biochanin A 98%min
  • Chickpea dentin A
  • 5,7-Dihydrox -4'-methoxyisoflavone
  • 4-Methylgenistein|||Olmelin
  • Biochanin A(P) (AHP Verified)
  • Biochanin A-RM
  • 491-80-5
  • Chromatography
  • Food &amp; Beverage Standards
  • Food Residue Analysis
  • Analytical Standards
  • Analytical Chromatography Product Catalog
  • BioChemical
  • Cancer Research
  • Anti-proliferative Agents
  • Chemopreventive Agents
  • chemical reagent
  • pharmaceutical intermediate
  • phytochemical
  • reference standards from Chinese medicinal herbs (TCM).