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D2016

Biochanin A

Synonym(s):

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

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100 mg
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CHF 73.90
1 g
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CHF 358.00

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
Form:
powder
Quality level:
100

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form

powder

Quality Level

100

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)

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.[1]

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.
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.

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This Item
92142PHL8001247752
Biochanin A

Sigma-Aldrich

D2016

Biochanin A

Biochanin A analytical standard

Supelco

92142

Biochanin A

Biochanin A phyproof® Reference Substance

PHL80012

Biochanin A

Formononetin ≥99.0% (TLC)

Sigma-Aldrich

47752

Formononetin

form

powder

form

-

form

powder

form

solid

Quality Level

100

Quality Level

100

Quality Level

-

Quality Level

100

mp

210-213 °C (lit.)

mp

210-213 °C (lit.)

mp

210-213 °C (lit.)

mp

257-261 °C

Gene Information

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

Gene Information

-

Gene Information

-

Gene Information

-

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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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Articles

Dietary Antioxidants

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.

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)
View All Related Papers

Global Trade Item Number

SKUGTIN
D2016-1G04061826016282
D2016-100MG04061833561362
D2016-250MG04061832407685

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