Substance

ID:183526

Names and Identifiers
IUPAC Traditional name
biochanin
IUPAC name
5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
Synonyms
Biochanin A5,7-Dihydroxy-4′-methoxyisoflavoneGenistein 4′-methyl ether
Registration numbers
CAS Number
Beilstein Number
EC Number
MDL Number
PubChem SID
Properties
Pharmacology Properties
Gene Information
human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)
Safety Information
German water hazard class
3
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Physical Property
Melting Point
210-213 °C(lit.)
Molecule Details
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.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D2016.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Molecular Spectra
No Data Available
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References
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