D2016

Biochanin A

• 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
• PubChem Substance ID: 24893597
• NACRES: NA.25

Properties

• form: powder
• 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)

Description

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.

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. 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
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves