92142

Biochanin A

analytical standard

• Synonym(s): 4′-Methylgenistein, 5,7-Dihydroxy-4′-methoxyisoflavone, Genistein 4′-methyl ether, Olmelin
• Empirical Formula (Hill Notation): C₁₆H₁₂O₅
• CAS Number: 491-80-5
• Molecular Weight: 284.26
• Beilstein: 278107
• EC Number: 207-744-7
• MDL number: MFCD00006839
• UNSPSC Code: 41116107
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• 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
• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable