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
Uses
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.
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Diethylstilbestrol is an olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.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).
