ContaminantDB: Daidzein

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (10)XML

Record Information

Version

1.0

Creation Date

2014-08-29 04:47:45 UTC

Update Date

2026-03-31 19:50:25 UTC

Accession Number

CHEM002924

Identification

Common Name

Daidzein

Class

Small Molecule

Description

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. (2, 1).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Ester
Food Toxin
Industrial/Workplace Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

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

Synonyms

Value	Source
4',7-Dihydroxyisoflavone	ChEBI
7,4'-Dihydroxyisoflavone	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone	ChEBI
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
Daidzeol	ChEBI
Isoaurostatin	ChEBI
Diadzein	MeSH
4',7-Dihydroxy-isoflavone	HMDB

Chemical Formula

C₁₅H₁₀O₄

Average Molecular Mass

254.241 g/mol

Monoisotopic Mass

254.058 g/mol

CAS Registry Number

486-66-8

IUPAC Name

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

Traditional Name

daidzein

SMILES

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

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

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

Substituents

Isoflavone
Hydroxyisoflavonoid
Chromone
Benzopyran
1-benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Pyran
Heteroaromatic compound
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

7-hydroxyisoflavones (CHEBI:28197 )
isoflavones (C10208 )
Isoflavonoids (C10208 )
Isoflavonoids (LMPK12050038 )
an isoflavone (DAIDZEIN )
a 4'-hydroxyisoflavone (DAIDZEIN )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

Chemical Roles

EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	323°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.085 g/L	ALOGPS
logP	3.3	ALOGPS
logP	2.73	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	6.48	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.7 m³·mol⁻¹	ChemAxon
Polarizability	25.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-001j-1928000000-f956e5fd0e616ef96161	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-000t-1619000000-eb2f87cd7d535b4d0446	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1928000000-f956e5fd0e616ef96161	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000t-1619000000-eb2f87cd7d535b4d0446	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001j-1927000000-87f11afa0cde5b353147	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-1390000000-0ff8f0de4d2d339f9357	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00gi-4229000000-71c73470904ad7b680ee	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-0090000000-20d2c8ade6aac1f46e8a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0udi-0970000000-a2349152106bd9da1257	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9100000000-691c394958fd19d47510	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0f7x-4900000000-5acb56232432597c00e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0pej-1930000000-89bedfb39603a12f3c75	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0490000000-c633d3449d8bb0206fc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0190000000-3a5de741e814e47d5cbe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-fb84819005f7f65b4fc8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-APPI-QQ (API2000) , Positive	splash10-0a4i-0090000000-b3ae695d217c756a5f8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive	splash10-0a4i-0090000000-d25bba2f5a1ac12e3d86	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0190000000-a9b6c8c416cb482a5dc1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0089-1970000000-f6070acf0fd663c4ae6f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0uem-1900000000-fa199caebb806e9eb0f9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-0490000000-3defe1cbaf29e0cd2d1f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0a4i-1790000000-2502633932fc66220039	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-0udi-0290000000-56b4c039a64ab57d3e70	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative	splash10-0089-2970000000-f32e85ba94cb6621d4f1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-6950000000-7b85969731514bf2d0bc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-388d21c85a84d4e0988a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-cc8371583b5ba50a4f0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0gbi-3950000000-cb120c48a579b9363f74	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-7dcbed418d38de120895	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0090000000-c522d590074eabe8c4c4	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

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. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

DAIDZEIN

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Baker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5.

MSDS

Link

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11193416

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16802696

3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23267126

4. https://www.ncbi.nlm.nih.gov/pubmed/?term=23337939

5. https://www.ncbi.nlm.nih.gov/pubmed/?term=23342971

6. https://www.ncbi.nlm.nih.gov/pubmed/?term=23439294

7. https://www.ncbi.nlm.nih.gov/pubmed/?term=9544566

8. Baker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5.

9. Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052.

10. Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857.

11. Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31.

12. Baker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5.

13. Jackman KA, Woodman OL, Sobey CG: Isoflavones, equol and cardiovascular disease: pharmacological and therapeutic insights. Curr Med Chem. 2007;14(26):2824-30.

14. Yuan JP, Wang JH, Liu X: Metabolism of dietary soy isoflavones to equol by human intestinal microflora--implications for health. Mol Nutr Food Res. 2007 Jul;51(7):765-81.

Daidzein (CHEM002924)

Structure for CHEM002924: Daidzein