Biochanin A

Structural formula
General
Surname	Biochanin A
other names	5,7-dihydroxy-3- (4-methoxyphenyl) -4 H -1-benzopyran-4-one; 5,7-dihydroxy-4'-methoxyisoflavone; Genistein 4'-methyl ether;
Molecular formula	C 16 H 12 O 5
Brief description	light yellow needles
External identifiers / databases
EC number	207-744-7
ECHA InfoCard	100.007.041
PubChem	5280373
ChemSpider	4444068
Wikidata	Q864222
properties
Molar mass	284.26 g mol −1
Physical state	firmly
Melting point	212 ° C
solubility	25 g l −1 (in acetone )
safety instructions
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Biochanin A belongs to the isoflavone class of flavonoids . It is also classified as phytoestrogens because it is a herbal, non- steroidal compound that has - weak - estrogen-like biological activity.

Occurrence

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

biosynthesis

Starting from the flavone apigenin , its (4-hydroxyphenyl) group is first rearranged from the 2-position to the 3-position, with a hydroxyl group being introduced at the 2-position under the influence of NADPH / H ⁺ and oxygen . The result is 2-hydroxy-2,3-dihydrogenistein, which enzymatically eliminates water and thus becomes genistein . Methylation of the hydroxy group in the 4-position of the phenyl radical with S- adenosylmethionine finally yields the biochanin A.

Individual evidence

↑ Entry on isoflavones. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.
↑ ^a ^b ^c Datasheet Biochanin A from Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).
↑ L. Bialesová, J. Brtko, V. Lenko, D. Macejová: Nuclear receptors - target molecules for isoflavones in cancer chemoprevention. In: General physiology and biophysics. Volume 32, Number 4, December 2013, pp. 467-478, doi : 10.4149 / gpb_2013064 . PMID 24067281 .

[Römpp-1] Entry on isoflavones. In: Römpp Online . Georg Thieme Verlag, accessed on June 20, 2014.

[sigma-aldrich-2] Datasheet Biochanin A from Sigma-Aldrich , accessed on May 25, 2011 ( PDF ).

[3] L. Bialesová, J. Brtko, V. Lenko, D. Macejová: Nuclear receptors - target molecules for isoflavones in cancer chemoprevention. In: General physiology and biophysics. Volume 32, Number 4, December 2013, pp. 467-478, doi : 10.4149 / gpb_2013064 . PMID 24067281 .