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Merck
CN

92142

Biochanin A

analytical standard

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C16H12O5
CAS Number:
Molecular Weight:
284.26
EC Number:
207-744-7
UNSPSC Code:
41116107
NACRES:
NA.24
Beilstein/REAXYS Number:
278107
MDL number:
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Product Name

Biochanin A, analytical standard

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

SMILES string

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

grade

analytical standard

assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

mp

210-213 °C (lit.)

application(s)

food and beverages

format

neat

Quality Level

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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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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