FComEx: Daidzein (PC000873)

Record Information

Version

1.0

Creation date

2015-10-09 22:33:10 UTC

Update date

2017-01-19 02:36:39 UTC

FoodComEx ID

PC000873

FoodDB Record

FDB002608

Chemical Information

Name

Daidzein

Description

Widespread isoflavone in the Leguminosae, especies Phaseolus subspecies (broad beans, lima beans); also found in soy and soy products (tofu, miso), chick peas (Cicer arietinum) and peanuts (Arachis hypogaea). Nutriceutical with anticancer and bone protective props. Daidzein is one of several known isoflavones. Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Up until recently, daidzein was considered to be one of the most important and most studied isoflavones, however more recently attention has shifted to isoflavone metabolites. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut. The clinical effectiveness of soy isoflavones may be a function of the ability to biotransform soy isoflavones to the more potent estrogenic metabolite, equol, which may enhance the actions of soy isoflavones, owing to its greater affinity for estrogen receptors, unique antiandrogenic properties, and superior antioxidant activity. However, not all individuals consuming daidzein produce equol. Only approximately one-third to one-half of the population is able to metabolize daidzein to equol. This high variability in equol production is presumably attributable to interindividual differences in the composition of the intestinal microflora, which may play an important role in the mechanisms of action of isoflavones. But, the specific bacterial species in the colon involved in the production of equol are yet to be discovered. (PMID: 18045128, 17579894, Curr Med Chem. 2007;14(26):2824-30., Mol Nutr Food Res. 2007 Jul;51(7):765-81.) Daidzein is a biomarker for the consumption of soy beans and other soy products. .

CAS Number

486-66-8

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
4',7-Dihydroxy-isoflavone	HMDB
4',7-Dihydroxyisoflavone	db_source
7-Hydroxy-3-(4-hydroxy-phenyl)-chromone	biospider
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone	biospider
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI	db_source
7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one	biospider
7,4'-Dihydroxyisoflavone	biospider
Daidzein	db_source
Daidzeol	db_source
Daizeol	db_source
Dimethylbiochanin B	db_source
Isoaurostatin	biospider
K 251-6	db_source
Tatoin	db_source

Chemical Formula

C15H10O4

IUPAC name

7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

InChI Identifier

InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H

InChI Key

ZQSIJRDFPHDXIC-UHFFFAOYSA-N

Isomeric SMILES

OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O

Average Molecular Weight

254.241

Monoisotopic Molecular Weight

254.057908802

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Isoflav-2-enes

Direct Parent

Isoflavones

Alternative Parents