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
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17574
ChEMBL	ChEMBL131921
ChemSpider	4444068
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829
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.^{[medical citation needed]} It has also been found to be a weak inhibitor of fatty acid amide hydrolase in vitro.^[2]

Metabolism[edit]

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).

^ 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.
^ 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.

v t e Isoflavones and their glycosides

Isoflavones	Daidzein Genistein Irilone Orobol Pseudobaptigenin Anagyroidisoflavone A and B

O-methylated isoflavones	Biochanin A Calycosin Formononetin Glycitein Irigenin 5-O-methylgenistein Pratensein Prunetin Psi-tectorigenin Retusin Tectorigenin

Glycosides	Daidzin Genistin Iridin Ononin Puerarin Sophoricoside Tectoridin

Prenylated isoflavones	Bidwillol A Derrubone Luteone 7-O-Methylluteone Wighteone

Pyranoisoflavones	Alpinumisoflavone Barbigerone Di-O-methylalpinumisoflavone 4'-methyl-alpinumisoflavone

Misc	Rotenoids

Synthetic	Ipriflavone

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^Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17574^Y
ChEMBL	ChEMBL131921^Y
ChemSpider	4444068^Y
ECHA InfoCard	100.007.041
IUPHAR/BPS	2829
KEGG	C00814^Y
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^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
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).
Y verify (what is ^YN ?)
Infobox references