Genistein

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Structural formula
Structural formula of genistein
General
Non-proprietary name Genistein
other names
  • 5,7-dihydroxy-3- (4-hydroxyphenyl) -4 H -chromen-4-one ( IUPAC )
  • 4 ', 5,7-trihydroxyisoflavone
Molecular formula C 15 H 10 O 5
Brief description

colorless powder

External identifiers / databases
CAS number 446-72-0
EC number 207-174-9
ECHA InfoCard 100.006.524
PubChem 5280961
ChemSpider 4444448
DrugBank DB01645
Wikidata Q415957
Drug information
Drug class

Phytoestrogens

properties
Molar mass 270.24 g · mol -1
Physical state

firmly

Melting point

297-298 ° C

solubility

soluble in ethanol and DMSO

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

500 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Genistein is a phytoestrogen from the group of isoflavonoids that occurs together with genistin in soybeans and red clover .

Red clover (Trifolium pratense)

pharmacology

Genistein is absorbed through food and can be detected in the serum of humans and animals.

Like other estrogens , genistein also leads to an accelerated capacitation of the sperm cells in the female genital tract - at the moment, however, it is also being investigated whether fertility might not be reduced by a premature acrosome reaction .

There are several indications that genistein, like another isoflavone ( daidzein ), slows down the transcription of the enzyme catechol-O-methyltransferase (COMT), which normally breaks down estradiol .

In tumor research, it is also examined whether the substance or the application of z. B. soy extracts have a positive effect on tumor growth, since genistein inhibits angiogenesis induced by FGF-2 due to the inhibition of tyrosine kinase, uPA (urokinase) and upregulation of PAI-1.

A tumor-inhibiting effect of the genistein could be demonstrated in both hormone-dependent and hormone-independent breast cancer cell lines. Experiments with genistein injections (exposure) in adult rats showed that the effect was greater when genistein injections were administered in the pubertal phase.

Individual evidence

  1. ↑ a b c d e data sheet Genistein at Sigma-Aldrich , accessed on April 3, 2011 ( PDF ).
  2. ↑ Genistein data sheet (PDF) from Carl Roth , accessed on December 14, 2010.
  3. ↑ Lehmann L, Jiang L, Wagner J: Soy isoflavones decrease the catechol-O-methyltransferase-mediated inactivation of 4-hydroxyestradiol in cultured MCF-7 cells . In: Carcinogenesis . 29, No. 2, February 2008, pp. 363-370. doi : 10.1093 / carcin / bgm235 . PMID 18192686 .
  4. ↑ FU Berlin: Estrogen Receptor Effects of Genistein , Section 1.6.3.1.