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Sigma-Aldrich

Biochanin A

Synonym(s):

4′-Methylgenistein, 5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether, Olmelin

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About This Item

Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
491-80-5
Molecular Weight:
284.26
Beilstein/REAXYS Number:
278107
EC Number:
207-744-7
MDL number:
MFCD00006839
UNSPSC Code:
41116107
PubChem Substance ID:
24893597
NACRES:
NA.25

form

powder

mp

210-213 °C (lit.)

SMILES string

COc1ccc(cc1)C2=COc3cc(O)cc(O)c3C2=O

InChI

1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3

InChI key

WUADCCWRTIWANL-UHFFFAOYSA-N

Gene Information

human ... CYP19A1(1588)
mouse ... Aldh1a2(19378) , Maoa(17161)

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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.

Application

Biochanin A has been used to evaluate its effect on the ergotamine (ERT)-induced contractility in bovine mesenteric vasculature. It may be used to test its anticancer potential in human glioblastoma cell lines. It has been used as a reference standard in high-performance liquid chromatography−tandem mass spectrometry.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Estrogenic effect of the phytoestrogen biochanin A in zebrafish, Danio rerio, and brown trout, Salmo trutta
Holbech H, et al.
Aquatic Toxicology (Amsterdam, Netherlands), 144, 19-25 (2013)
Interaction of isoflavones and endophyte-infected tall fescue seed extract on vasoactivity of bovine mesenteric vasculature
Jia Y, et al.
Frontiers in nutrition, 2(9), 32-32 (2015)
Combination of Biochanin A and Temozolomide Impairs Tumor Growth by Modulating Cell Metabolism in Glioblastoma Multiforme
Desai V, et al.
Anticancer research, 39(1), 57-66 (2019)
Sunil Kumar Manna
Biochemical pharmacology, 83(10), 1383-1392 (2012-03-06)
Several protein tyrosine kinase (PTK) inhibitors predominantly isoflavones, such as genistein, erbstatin, quercetin, daidzein, present in red clover, cabbage and alfalfa, show apoptotic effect against cancer cells. In this study I found that biochanin, a methoxy form of genistein, inhibits
Nikolas Fokialakis et al.
Bioorganic & medicinal chemistry, 20(9), 2962-2970 (2012-04-03)
Biochanin A (BCA), a major isoflavone in red clover and many other legumes, has been reported to display estrogenic as well as cancer chemopreventive properties. Ingested BCA is known to display low bioavailability due to poor solubility, extensive metabolism and
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