Biochanin A
Chemical compound
From Wikipedia, the free encyclopedia
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.
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| Names | |
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| 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) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.041 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| 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).
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Biochanin A is classified as a phytoestrogen. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.[2]
Metabolism
The enzyme biochanin-A reductase converts biochanin A to 2,3-dihydrobiochanin A using nicotinamide adenine dinucleotide phosphate (NADPH) as its cofactor.[3]
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).