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HomeProduct name listDiethylstilbestrol

Diethylstilbestrol

Synonym(s):DES

  • CAS NO.:6898-97-1
  • Empirical Formula: C18H20O2
  • Molecular Weight: 268.35
  • MDL number: MFCD00002373
  • EINECS: 678-392-3
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-11 15:07:33
Diethylstilbestrol Structural

What is Diethylstilbestrol?

Description

Diethylstilbestrol is a derivative of stilbene, and it differs from sin-estrol by the presence of a double bond with trans-configuration of the two phenyl groups. In terms of estrogenic activity, this drug surpasses both estrone and hexestrol.

Chemical properties

White solid

The Uses of Diethylstilbestrol

Diethylstilbestrol was used as internal standard for the analysis of drug residues in urine of rats and calves by on-line HPLC with ultraviolet and continuous-flow fast atom bombardmentmass spectrometry detectors.

What are the applications of Application

Diethylstilbestrol, mixture of cis and trans is a synthetic estrogen and HPLC internal standard

Definition

ChEBI: Diethylstilbestrol is an olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups. It has a role as an antineoplastic agent, a carcinogenic agent, a xenoestrogen, an EC 3.6.3.10 (H(+)/K(+)-exchanging ATPase) inhibitor, an antifungal agent, an endocrine disruptor, an EC 1.1.1.146 (11beta-hydroxysteroid dehydrogenase) inhibitor, an autophagy inducer and a calcium channel blocker. It is a polyphenol and an olefinic compound.

General Description

Mechanisms of the isomerization processes of molecular and anionic diethylstilbestrol (DES) has been reported. Estrogen activity of cis- and trans-diethylstilbestrol has been evaluated. Diethylstilbestrol is a carcinogenic synthetic estrogen.

Synthesis

Diethylstilbestrol, trans-|á,|?-diethyl-4,4-stilbendiol (28.1.34), is proposed to be synthesized in various ways. According to one of them, desoxyansoine is alkylated by ethyl iodide in the presence of sodium ethoxide, and the resulting ketone (28.1.30) is reacted in a Grignard reaction with ethylmagnesium bromide, which forms the carbinol (28.1.31). Dehydration of this compound by distillation in the presence of p-toluenesulfonic acid gives dimethyl ether of stilbestrol (28.1.32), methyl groups of which are removed by heating it at high temperatures with potassium hydroxide, thus forming diethylstilbestrol (28.1.33).

Synthesis_6898-97-1

Properties of Diethylstilbestrol

Melting point: 170-172 °C(lit.)
Boiling point: 407.1±25.0 °C(Predicted)
Density  1.107±0.06 g/cm3(Predicted)
solubility  soluble in Methanol
form  powder to crystal
pka 9.27±0.15(Predicted)
color  White to Almost white
Merck  14,3129
CAS DataBase Reference 6898-97-1

Safety information for Diethylstilbestrol

Signal word Danger
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
ghs
Health Hazard
GHS08
ghs
Environment
GHS09
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
H350:Carcinogenicity
H410:Hazardous to the aquatic environment, long-term hazard
Precautionary Statement Codes P202:Do not handle until all safety precautions have been read and understood.
P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P273:Avoid release to the environment.
P302+P352:IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for Diethylstilbestrol

InChIKey RGLYKWWBQGJZGM-ISLYRVAYSA-N

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