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 in soy, in alfalfa sprouts, in peanuts, in chickpea (Cicer arietinum) and in other legumes.

Biochanin A
Names
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.041
KEGG
UNII
  • 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
  • O=C\1c3c(O/C=C/1c2ccc(OC)cc2)cc(O)cc3O
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).
Y verify (what is YN ?)
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.

Biochanin A can block the vasoconstriction in a dose-dependent manner due to the inhibition of L-type calcium channels. Such vasodilatory effect, in micromolar concentrations, is of potential clinical interest for the management of cardiovascular pathologies.

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