Diethylstilbestrol (CHEM003701)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (9)XML
Record Information
Version1.0
Creation Date2014-09-11 05:14:27 UTC
Update Date2026-03-31 19:50:24 UTC
Accession NumberCHEM003701
Identification
Common NameDiethylstilbestrol
ClassSmall Molecule
DescriptionA synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders. It was also used formerly as a growth promoter in animals. According to the Fourth Annual Report on Carcinogens (NTP 85-002, 1985), diethylstilbestrol has been listed as a known carcinogen.
Contaminant Sources
  • Clean Air Act Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • IARC Carcinogens Group 1
  • My Exposome Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Carcinogen
  • Drug
  • Estrogen, Non-Steroidal
  • Food Toxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-3,4-Bis(4-hydroxyphenyl)-3-hexeneChEBI
(e)-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenolChEBI
4,4'-Dihydroxy-alpha,beta-diethylstilbeneChEBI
alpha,Alpha'-diethyl-(e)-4,4'-stilbenediolChEBI
DESChEBI
DiethylstilbestrolumChEBI
DietilestilbestrolChEBI
DistilbeneChEBI
trans-4,4'-(1,2-Diethyl-1,2-ethenediyl)bisphenolChEBI
trans-DiethylstilbesterolChEBI
trans-DiethylstilbestrolChEBI
trans-DiethylstilboesterolChEBI
StilbestrolKegg
4,4'-Dihydroxy-a,b-diethylstilbeneGenerator
4,4'-Dihydroxy-α,β-diethylstilbeneGenerator
a,Alpha'-diethyl-(e)-4,4'-stilbenediolGenerator
Α,alpha'-diethyl-(e)-4,4'-stilbenediolGenerator
AgostilbenMeSH
ApstilMeSH
Diethylstilbestrol, (Z)-isomerMeSH
Diethylstilbestrol, disodium saltMeSH
DistilbèneMeSH
Estrogen, stilbeneMeSH
Stilbene estrogenMeSH
TampovaganMeSH
co Pharma brand OF diethylstilbestrolMeSH
Gerda brand OF diethylstilbestrolMeSH
APS brand OF diethylstilbestrolMeSH
CO-Pharma brand OF diethylstilbestrolMeSH
Chemical FormulaC18H20O2
Average Molecular Mass268.356 g/mol
Monoisotopic Mass268.146 g/mol
CAS Registry Number56-53-1
IUPAC Name4-[(3E)-4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol
Traditional Nameestrogen
SMILESCC\C(=C(\CC)C1=CC=C(O)C=C1)C1=CC=C(O)C=C1
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/b18-17+
InChI KeyRGLYKWWBQGJZGM-ISLYRVAYSA-N
Chemical Taxonomy
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 Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point172°C
Boiling PointNot Available
Solubility12 mg/L (at 25°C)
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.62ALOGPS
logP5.19ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)8.63ChemAxon
pKa (Strongest Basic)-6.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity83.24 m³·mol⁻¹ChemAxon
Polarizability30.68 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0290000000-f2a65d0f5428a0bf0096Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0159-0690000000-6b39aa057a8cb6eb1defSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-001i-2950000000-4f5e80bdea64d9365cc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-9bda79387111e5798094Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0090000000-7c62326707d11881c098Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ll-2490000000-de50c09ba9f659d1b047Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014r-0890000000-ce8b26781cf43b806840Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00kr-0930000000-ff4502b2ae61ffdf7a9aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052p-1950000000-6890970b5e5ae4ffaf87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-e89c3535f3d6cda6ed7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ap0-0190000000-93dd0c6a4d49918f7fc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0300-0790000000-15fa3a704fd6a8d70eabSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityEstrogens diffuse into their target cells and interact with a protein receptor, the estrogen receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. The effect of Estrogen binding their receptors causes downstream increases the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
MetabolismHepatic.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (6)
Uses/SourcesUsed in the treatment of prostate cancer. Previously used in the prevention of miscarriage or premature delivery in pregnant women prone to miscarriage or premature delivery.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include nausea and vomiting, and withdrawal bleeding may occur in females.
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0302859
FooDB IDFDB006560
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDiethylstilbestrol
Chemspider ID395306
ChEBI ID41922
PubChem Compound ID448537
Kegg Compound IDC07620
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Adler, E.,Gie, G.J. and von Euler, H.; US. Patent 2,421,401; June 3, 1947; assigned to Hoffmann-La Roche, Inc.

MSDSLink
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12877905
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15322263
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16665969
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19303142
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=21795073
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=21852823
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=24247716
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=25934356
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=28461243
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=29344720
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=29609831
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=29658110
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=30049842
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=30153466
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=30594671
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=30685453
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=30758926
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=30866048
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=31119342
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=31119346
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=31247589
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=31259848
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=31280197
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=31283846
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=31300300
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=8832405
27. https://www.ncbi.nlm.nih.gov/pubmed/?term=9202463