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Merck
모든 사진(1)

문서

D2016

Sigma-Aldrich

Biochanin A

동의어(들):

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

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About This Item

실험식(Hill 표기법):
C16H12O5
CAS Number:
Molecular Weight:
284.26
Beilstein:
278107
EC Number:
MDL number:
UNSPSC 코드:
41116107
PubChem Substance ID:
NACRES:
NA.25

형태

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

유전자 정보

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관련 카테고리

일반 설명

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.

애플리케이션

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.

생화학적/생리학적 작용

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point (°F)

Not applicable

Flash Point (°C)

Not applicable

개인 보호 장비

Eyeshields, Gloves, type N95 (US)


시험 성적서(COA)

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문서 라이브러리 방문

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)
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)
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)
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

문서

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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