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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)

Certificados de análisis (COA)

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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)
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)
Evelyne Reiter et al.
Gynecological endocrinology : the official journal of the International Society of Gynecological Endocrinology, 27(12), 1037-1042 (2011-08-02)
Isoflavones from red clover and soy plant extracts are used in highly concentrated food supplements as an alternative to hormone replacement therapy. Due to their estrogenic activity, isoflavones are a focus of safety concerns about their potential to promote the
Hyo-Kyung Han et al.
Die Pharmazie, 66(9), 710-715 (2011-10-27)
The present study aimed to improve the in vivo effectiveness of biochanin A as a P-gp inhibitor by formulation in solid dispersion (SD). SDs were prepared with Solutol HS15 and hydroxypropylmethyl cellulose (HPMC2910) and their inhibition effect on P-gp mediated
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