Biochanin A is an O-methylated isoflavone. It is a natural organic compound in the class of phytochemicals known as flavonoids. Biochanin A can be found in red clover[1] in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes.
 | |
 | |
| Names | |
|---|---|
| IUPAC name 5,7-Dihydroxy-4′-methoxyisoflavone | |
| Systematic IUPAC name 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-1-benzopyran-4-one | |
| Other names Biochanin 4′-Methylgenistein olmelin Biochanine A Biochanin-A Genistein 4-methyl ether | |
| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.041 |
| KEGG | |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
| |
| |
| Properties | |
| C16H12O5 | |
| Molar mass | 284.267 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis.[medical citation needed] It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.[2]
Biochanin A can block the vasoconstriction in a dose-dependent manner due to the inhibition of L-type calcium channels. Such vasodilatory effect, in micromolar concentrations, is of potential clinical interest for the management of cardiovascular pathologies.[3]
Metabolism
The enzyme biochanin-A reductase uses dihydrobiochanin A and NADP+ to produce biochanin A, NADPH, and H+. The enzyme isoflavone-7-O-beta-glucoside 6"-O-malonyltransferase uses malonyl-CoA and biochanin A 7-O-β-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-β-D-glucoside).