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

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
Molecular Weight:
284.26
MDL Number:
MFCD00006839
MOL File:
491-80-5.mol
MSDS File:
SDS
Last updated:2024-11-19 15:53:33

5,7-Dihydrox -4'-methoxyisoflavone Properties

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
pka 6.50±0.20(Predicted)
form Powder
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)
EWG's Food Scores 1
NCI Dictionary of Cancer Terms biochanin A
FDA UNII U13J6U390T
EPA Substance Registry System 4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-methoxyphenyl)- (491-80-5)

SAFETY

Risk and Safety Statements

Safety Statements  22-24/25
WGK Germany  3
RTECS  DJ3002500
10
TSCA  Yes
HS Code  29329990
NFPA 704
1
0 0

5,7-Dihydrox -4'-methoxyisoflavone price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHL80012 Biochanin A phyproof? Reference Substance 491-80-5 25MG $259 2024-03-01 Buy
Sigma-Aldrich 92142 Biochanin A analytical standard 491-80-5 50mg $183 2024-03-01 Buy
Sigma-Aldrich 1071381 Biochanin A United States Pharmacopeia (USP) Reference Standard 491-80-5 20mg $344 2024-03-01 Buy
TCI Chemical B4098 Biochanin A >98.0%(HPLC)(T) 491-80-5 1g $217 2024-03-01 Buy
TCI Chemical B4098 Biochanin A >98.0%(HPLC)(T) 491-80-5 5g $728 2024-03-01 Buy
Product number Packaging Price Buy
PHL80012 25MG $259 Buy
92142 50mg $183 Buy
1071381 20mg $344 Buy
B4098 1g $217 Buy
B4098 5g $728 Buy

5,7-Dihydrox -4'-methoxyisoflavone Chemical Properties,Uses,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

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

phytoestrogen

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.

487-70-7
2632-13-5
491-80-5
Synthesis of 5,7-Dihydrox -4'-methoxyisoflavone from 2,4,6-TRIHYDROXYBENZALDEHYDE and 2-Bromo-4'-methoxyacetophenone
Global( 383)Suppliers
Supplier Tel Email Country ProdList Advantage
Shaanxi Dideu Medichem Co. Ltd
18192627656 1012@dideu.com China 3002 58
Capot Chemical Co.,Ltd.
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18017610038 zheyansh@163.com CHINA 3619 58
career henan chemical co
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Shaanxi Yikanglong Biotechnology Co., Ltd.
17791478691 yklbiotech@163.com CHINA 296 58
Chengdu Biopurify Phytochemicals Ltd.
+8618080483897 sales@biopurify.com China 3772 58

View Lastest Price from 5,7-Dihydrox -4'-methoxyisoflavone manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Biochanin A pictures 2024-11-19 Biochanin A
491-80-5
US $30.00-46.00 / mg 97.69% 10g TargetMol Chemicals Inc.
5,7-Dihydrox -4'-methoxyisoflavone pictures 2024-07-08 5,7-Dihydrox -4'-methoxyisoflavone
491-80-5
US $1.00-100.00 / KG 1KG 99% 4000KG Shaanxi Dideu Medichem Co. Ltd
5,7-Dihydrox -4'-methoxyisoflavone pictures 2024-03-28 5,7-Dihydrox -4'-methoxyisoflavone
491-80-5
US $0.00 / kg 25kg HPLC>99% Inquiry PNP Biotech Co. Ltd
  • Biochanin A pictures
  • Biochanin A
    491-80-5
  • US $30.00-46.00 / mg
  • 97.69%
  • TargetMol Chemicals Inc.
5,7-DIHYDROXY-4''-METHOXYISOFLAVONE, 98% BIOCHANIN A 5,7-Dihydrox -4'-methoxyisoflavone 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 NSC 123538 Biochanin A (4-Methylgenistein) Biochanin A,5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether 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 5,7-DIHYDROXY-4'-METHOXYISOFLAVONE 5,7-DIHYDROXY-4-METHOXYISOFLAVONE 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 5,7-Dihydrox -4'-methoxyisoflavone 491-80-5 7-hydroxy-3-(4-methoxyphenyl)-4-oxo-1-benzopyran-5-olate Biochanin A > Genistein Methyl Ether Chickpea bud A 5,7-Dihydroxy-4'-methoxyisoflavone (Biochanin A) TIANFUCHEM--High purity 491-80-5 5,7-Dihydrox -4'-methoxyisoflavone Biochani,Olmelin 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one BIOCHANIN A (AHP) BIOCHANIN 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one Bilchanin A OlMelin Pratensol BIOCHANIN A Genistein 4′-methyl ether 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 & 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).