Biochanin A

Biochanin A
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 Y
PubChem	5280373
ChemSpider	4444068 Y
KEGG	C00814 Y
ChEBI	CHEBI:17574 Y
ChEMBL	CHEMBL131921 Y
Jmol-3D images	Image 1
SMILES O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
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 Y Key: WUADCCWRTIWANL-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C16H12O5
Molar mass	284.26 g/mol
Exact mass	284.068473
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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-beta-D-glucoside to produce CoA and biochanin A 7-O-(6-O-malonyl-beta-D-glucoside).

References

1. ^ Red clover isoflavones biochanin A and formononetin are potent ligands of the human aryl hydrocarbon receptor, The Journal of Steroid Biochemistry and Molecular Biology, Volume 108, Issues 1-2, January 2008, S. Medjakovic, A. Jungbauer.

See also

• List of phytochemicals in food