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MilliporeSigma

D2016

Biochanin A

Synonym(s):

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

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$112.00

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About This Item

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

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InChI key

WUADCCWRTIWANL-UHFFFAOYSA-N

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

SMILES string

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

form

powder

mp

210-213 °C (lit.)

Quality Level

100

Gene Information

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

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This Item
92142PHL800121071381
Biochanin A

Sigma-Aldrich

D2016

Biochanin A

Biochanin A analytical standard

Supelco

92142

Biochanin A

Biochanin A phyproof® Reference Substance

PHL80012

Biochanin A

Biochanin A United States Pharmacopeia (USP) Reference Standard

USP

1071381

Biochanin A

form

powder

form

-

form

powder

form

-

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

-

mp

210-213 °C (lit.)

mp

210-213 °C (lit.)

mp

210-213 °C (lit.)

mp

210-213 °C (lit.)

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

Application

Biochanin A has been used to evaluate its effect on the ergotamine (ERT)-induced contractility in bovine mesenteric vasculature.[1] It may be used to test its anticancer potential in human glioblastoma cell lines.[2] It has been used as a reference standard in high-performance liquid chromatography−tandem mass spectrometry.[3]

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.
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.

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.[4]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
STBJ7906
S39234
066K1687
128H0483
109F3739

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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)
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)
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
Young Jin Seo et al.
Journal of Korean medical science, 26(11), 1489-1494 (2011-11-09)
Natural isoflavones and flavones are important dietary factors for prostate cancer prevention. We investigated the molecular mechanism of these compounds (genistein, biochanin-A and apigenin) in PC-3 (hormone-independent/p53 mutant type) and LNCaP (hormone-dependent/p53 wild type) prostate cancer cells. A cell growth
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