Biochanin A

  • Biochanin A
  • 5,7-dihydroxy -3-( 4-methoxyphenyl) -4H- 1-benzopyran -4-one
  • 5,7-dihydroxy -4 '- methoxyisoflavone
  • Genistein -4'- methyl ether

Light yellow needles

Fixed

212 ° C

25 g · l -1 ( in acetone)

Template: Infobox chemical / molecular formula search available

Biochanin A belongs to the isoflavone class of flavonoids. It is also assigned to the phyto-oestrogens, as it is a vegetable, non-steroidal compound having estrogen-like biological activity. Biochanin A has weak estrogenic activity.

Occurrence

Biochanin A was found in certain legume species, mainly in red clover (also called red clover ).

Biosynthesis

Starting from the flavone apigenin the (4- hydroxyphenyl ) group is first migrated from the 2- position to the 3- position, under the influence of NADPH / H , and oxygen at the 2- position a hydroxyl group is introduced. The result is the 2-hydroxy- 2 ,3- dihydrogenistein, which enzymatically eliminated water and thus to genistein. Methylation of the hydroxy group in the 4- position of the phenyl radical and the S -adenosyl methionine, finally supplies the biochanin A.

CAS registry number PubChem Phenyl group
125937
de