Biochanin A

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	491-80-5
ChEBI	CHEBI:17574
ChEMBL	ChEMBL131921
ChemSpider	4444068
IUPHAR/BPS	2829
Jmol interactive 3D	Image
KEGG	C00814
PubChem	5280373
InChI 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 Key: WUADCCWRTIWANL-UHFFFAOYSA-N InChI=1/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 Key: WUADCCWRTIWANL-UHFFFAOYAM
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
Properties
Chemical formula	C16H12O5
Molar mass	284.27 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 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 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, J. J.; Alter, B. J.; McKinney, M. K.; Cravatt, B. F.; Ross, R. A.; Pertwee, R. G.; Gereau, R. W. 4th; Wiley, J. L.; Fowler, C. J. (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.