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D2016

Sigma-Aldrich

Biochanin A

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C16H12O5
Número de CAS:
491-80-5
Peso molecular:
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)

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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)
Sheelendra Pratap Singh et al.
Phytotherapy research : PTR, 26(2), 303-307 (2011-12-02)
The aim of this study was to investigate the effect of biochanin A (BCA) on the pharmacokinetics of tamoxifen, a substrate of P-glycoprotein (P-gp) and cytochrome 3A (CYP3A), in female rats. The tamoxifen was administered orally (10 mg/kg) without or with
Zhongliu Zhou et al.
Molecules (Basel, Switzerland), 17(11), 12636-12641 (2012-10-27)
Two novel compounds, 1α-methoxy-3β-hydroxy-4α-(3′,4′-dihydroxyphenyl)-1, 2,3,4-tetrahydronaphthalin (1) and 1α,3β-dihydroxy-4α-(3′,4′-dihydroxyphenyl)-1,2,3,4-tetrahydronaphthalin (2), were isolated along with six known compounds 3-8 from the rhizomes of Cyperus rotundus. This paper reports the isolation and full spectroscopic characterization of these new compounds by NMR, UV, IR
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