Record Information
Version1.0
Creation date2010-04-08 22:07:38 UTC
Update date2019-11-26 03:01:41 UTC
Primary IDFDB007498
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDiethylstilbesterol
DescriptionDiethylstilbestrol, also known as DES, belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Diethylstilbestrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Diethylstilbestrol is found, on average, in the highest concentration within gram beans. This could make diethylstilbestrol a potential biomarker for the consumption of these foods. Diethylstilbestrol is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound.
CAS Number56-53-1
Structure
Thumb
Synonyms
SynonymSource
DESHMDB
DiethylstilbesterolHMDB
Diethylstilbestrol BPHMDB
DiethylstilboesterolHMDB
DietilestilbestrolHMDB
Percutatrine oestrogenique iscovescoHMDB
Rcra waste number u089HMDB
trans-DiethylstilbesterolHMDB
trans-DiethylstilbestrolHMDB
trans-DiethylstilboesterolHMDB
(E)-3,4-bis(4-hydroxyphenyl)-3-hexenemanual
(E)-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenolmanual
4,4'-Dihydroxy-a,b-diethylstilbeneGenerator
4,4'-dihydroxy-alpha,beta-diethylstilbenemanual
4,4'-Dihydroxy-α,β-diethylstilbeneGenerator
a,Alpha'-diethyl-(e)-4,4'-stilbenediolGenerator
alpha,alpha'-diethyl-(E)-4,4'-stilbenediolmanual
Diethylstilbestrolmanual
Diethylstilbestrol bpHMDB
DiethylstilbestrolumChEBI
DistilbeneChEBI
trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenolmanual
α,alpha'-diethyl-(e)-4,4'-stilbenediolGenerator
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.62ALOGPS
logP5.19ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.13ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.24 m³·mol⁻¹ChemAxon
Polarizability30.69 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H20O2
IUPAC name4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
InChI IdentifierInChI=1S/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3
InChI KeyRGLYKWWBQGJZGM-UHFFFAOYSA-N
Isomeric SMILESCCC(=C(CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
Average Molecular Weight268.3502
Monoisotopic Molecular Weight268.146329884
Classification
Description Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassStilbenes
Sub ClassNot Available
Direct ParentStilbenes
Alternative Parents
Substituents
  • Stilbene
  • Phenylpropane
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Environmental role:

Industrial application:

Indirect biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point170.5 oC
Boiling PointNot Available
Experimental Water Solubility0.012 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP5.07HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSDiethylstilbesterol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0390000000-d064f732675ea9894f2cSpectrum
Predicted GC-MSDiethylstilbesterol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0awa-1019000000-1cc583dcfd41002dd339Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-f2a65d0f5428a0bf0096Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0690000000-6b39aa057a8cb6eb1defSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2950000000-4f5e80bdea64d9365cc7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-9bda79387111e5798094Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-7c62326707d11881c098Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ll-2490000000-de50c09ba9f659d1b047Spectrum
NMRNot Available
ChemSpider ID395306
ChEMBL IDCHEMBL411
KEGG Compound IDC07620
Pubchem Compound ID448537
Pubchem Substance IDNot Available
ChEBI ID4531
Phenol-Explorer IDNot Available
DrugBank IDDB00255
HMDB IDHMDB14400
CRC / DFC (Dictionary of Food Compounds) IDBGS42-Y:BGS42-Y
EAFUS IDNot Available
Dr. Duke IDDIETHYLSTILBESTEROL
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDDES
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDiethylstilbestrol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Estrogen receptor betaESR2Q92731
Estrogen receptorESR1P03372
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).