Biochanin A

• Catalog No.: D2016
• CAS Number: 491-80-5
• M. F.: C16H12O5
• M. W.: 284.26348

SYNONYMS

• IUPAC name: 5,7-dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one
• IUPAC Traditional name: biochanin
• Synonyms: 5,7-Dihydroxy-4′-methoxyisoflavone; Genistein 4′-methyl ether

DATABASE IDS

• CAS Number: 491-80-5
• EC Number: 207-744-7
• PubChem SID: 24893597
• MDL Number: MFCD00006839
• Beilstein Number: 278107

PROPERTIES

• Gene Information: human ... CYP19A1(1588)mouse ... Aldh1a2(19378), Maoa(17161)
• Melting Point: 210-213 °C(lit.)
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• German water hazard class: 3

DETAILS

Description (English)

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.