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Diethylstilbestrol

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Diethylstilbestrol Basic information

Product Name:
Diethylstilbestrol
Synonyms:
  • DIETHYLSTILBESTROL 97% MIXTURE OF CIS&
  • diethylstilbestrol, mixture of cis and trans
  • Diethylstilbestrol,mixture of cis and trans
  • DIETHYLSTILBESTROL, 99%, MIXTURE OF CIS AND TRANS
  • 3,4-Bis(4-hydroxyphenyl)-3-hexene
  • 4,4'-(1,2-Diethylvinylene)bisphenol
  • 4,4'-(3-Hexene-3,4-diyl)bisphenol
  • 3,4-Bis(4-hydroxypheny
CAS:
6898-97-1
MF:
C18H20O2
MW:
268.35
EINECS:
678-392-3
Product Categories:
  • Acyclic
  • Alkenes
  • Bioactive Small Molecules
  • Building Blocks
  • Cell Biology
  • Chemical Synthesis
  • Stilbenes
  • D-DIF
  • Organic Building Blocks
Mol File:
6898-97-1.mol
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Diethylstilbestrol Chemical Properties

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
InChIKey
RGLYKWWBQGJZGM-ISLYRVAYSA-N
CAS DataBase Reference
6898-97-1
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Safety Information

Hazard Codes 
T,N
Risk Statements 
45-61-36/37/38-51/53
Safety Statements 
53-36/37/39-45-60-61
RIDADR 
UN 3077 9/PG 3
WGK Germany 
3
RTECS 
WJ5600000
HazardClass 
9
PackingGroup 
III
HS Code 
29072990
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Diethylstilbestrol Usage And Synthesis

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Diethylstilbestrol is an olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.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

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