Diethylstilbestrol

Names

[ CAS No. ]:
56-53-1

[ Name ]:
Diethylstilbestrol

[Synonym ]:
Stilboesterol
trans-Diethyl Stilbestrol
Stil
Percutacrine Oestrogenique Iscovesco
Sibol
4,4'-Stilbenediol, α,α'-diethyl-, (E)-
stilboestrol
4,4'-hex-3-ene-3,4-diyldiphenol
cyrena
Synthestrin
Monozol
Diethylstilbestrol
4,4'-Stilbenediol, α,α'-diethyl-
Phenol, 4,4'-[(E)-1,2-diethyl-1,2-ethenediyl]bis-
4,4'-(3E)-hex-3-ene-3,4-diyldiphenol
Estril
(E)-3,4-Bis(p-hydroxyphenyl)-3-hexene
Bufon
Desma
Cyren
4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
4,4'-[(3E)-3-Hexene-3,4-diyl]diphenol
a,a'-Diethylstilbenediol
Estrogenine
4,4'-[(1E)-1,2-Diethyl-1,2-ethenediyl]bisphenol
MFCD00002373
α,α'-Diethyl-4,4'-stilbenediol
DES
(E)-a,a'-Diethyl-4,4'-stilbenediol
EINECS 200-278-5
trans-α,α'-Diethyl-4,4'-stilbenediol
DES (VAN)
4,4'-Dihydroxy-a,b-diethylstilbene
OeKolp

Biological Activity

[Description]:

Diethylstilbestrol, a synthetic nonsteroidal estrogen used in the treatment of menopausal and postmenopausal disorders.Target: Estrogen Receptor/ERRDiethylstilbestrol (DES), a synthetic estrogen that was used in pregnancy, is a prototype endocrine-disrupting chemical. Although prenatal exposure to DES is known to increase risks of vaginal/cervical adenocarcinoma and adverse reproductive outcomes in women, and urogenital anomalies in men, data on nonreproductive medical conditions are lacking. Comparing persons exposed prenatally to DES with those who were not exposed, the hazard ratios were 1.21 (95% confidence interval = 0.96-1.54) for diabetes, 1.27 (1.00-1.62) for all cardiovascular disease, 1.18 (0.88-1.59) for coronary artery disease, 1.28 (0.88-1.86) for myocardial infarction, 1.12 (1.02-1.22) for high cholesterol, 1.14 (1.02-1.28) for hypertension, 1.24 (0.99-1.54) for osteoporosis, and 1.30 (0.95-1.79) for fractures. The associations did not differ by dose and timing of DES exposure, nor, in the women, by the presence or absence of vaginal epithelial changes (a marker of DES host susceptibility) [1]. The role of prenatal exposure to DES as an environmental risk factor for psychiatric disorders requires more evidence before any conclusions can be drawn [2].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Endocrinology

[References]

[1]. Troisi, R., et al., Medical conditions among adult offspring prenatally exposed to diethylstilbestrol. Epidemiology, 2013. 24(3): p. 430-8.

[2]. Kebir, O. and M.O. Krebs, Diethylstilbestrol and risk of psychiatric disorders: a critical review and new insights. World J Biol Psychiatry, 2012. 13(2): p. 84-95.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
407.1±25.0 °C at 760 mmHg

[ Melting Point ]:
170-172 °C(lit.)

[ Molecular Formula ]:
C₁₈H₂₀O₂

[ Molecular Weight ]:
268.350

[ Flash Point ]:
186.9±17.8 °C

[ Exact Mass ]:
268.146332

[ PSA ]:
40.46000

[ LogP ]:
5.93

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.603

[ Storage condition ]:
0-6°C

[ Stability ]:
Isomerizes rapidly in Benzene, Chloroform, and Ether.Keep Shielded from light.

[ Water Solubility ]:
PRACTICALLY INSOLUBLE

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07, GHS08, GHS09

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H319-H335-H350-H360-H410

[ Precautionary Statements ]:
P201-P280-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves;type P2 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R40;R45;R61;R36/37/38;R51/53

[ Safety Phrases ]:
S53-S36/37/39-S45-S60-S61

[ RIDADR ]:
UN 3077 9/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
WJ5600000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2942000000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2942000000

Articles

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Extending an in vitro panel for estrogenicity testing: the added value of bioassays for measuring antiandrogenic activities and effects on steroidogenesis.

Toxicol. Sci. 141(1) , 78-89, (2014)

In the present study, a previously established integrated testing strategy (ITS) for in vitro estrogenicity testing was extended with additional in vitro assays in order to broaden its sensitivity to ...

Analysis of endocrine disrupters and related compounds in sediments and sewage sludge using on-line turbulent flow chromatography-liquid chromatography-tandem mass spectrometry.

J. Chromatogr. A. 1352 , 29-37, (2014)

A novel fully automated method based on dual column switching using turbulent flow chromatography followed by liquid chromatography coupled to tandem mass spectrometry (TFC-LC-MS/MS) was applied for t...