Biochanin A

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.

Biochanin A
Names
IUPAC name
5,7-Dihydroxy-3-(4-methoxyphenyl)chromen-4-one
Other names
Biochanin
4'-Methylgenistein
olmelin
Biochanine A
Biochanin-A
Genistein 4-methyl ether
5,7-Dihydroxy-4'-methoxyisoflavone
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.041
KEGG
PubChem CID
Properties
Chemical formula
 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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Infobox references

Biochanin A is classified as a phytoestrogen and has putative benefits in dietary cancer prophylaxis. It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.[2]

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).

See also
  • List of phytochemicals in food

References
  1. Medjakovic, S.; Jungbauer, A. (2008). "Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor". The Journal of Steroid Biochemistry and Molecular Biology. 108 (1–2): 171–177. doi:10.1016/j.jsbmb.2007.10.001. PMID 18060767.
  2. Thors L, Burston JJ, Alter BJ, McKinney MK, Cravatt BF, Ross RA, Pertwee RG, Gereau RW, Wiley JL, Fowler CJ (2010). "Biochanin A, a naturally occurring inhibitor of fatty acid amide hydrolase". British Journal of Pharmacology. 160 (3): 549–560. doi:10.1111/j.1476-5381.2010.00716.x. PMC 2931556. PMID 20590565.
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