3,4-Bis(4′-hydroxyphenyl)-3-hexene
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: 2026-01-13 11:13:18
What is 3,4-Bis(4′-hydroxyphenyl)-3-hexene?
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 3,4-Bis(4′-hydroxyphenyl)-3-hexene
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Diethylstilbestrol is an olefinic compound that is trans-hex-3-ene in which the hydrogens at positions 3 and 4 have been replaced by p-hydroxyphenyl groups.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).
Properties of 3,4-Bis(4′-hydroxyphenyl)-3-hexene
| 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 3,4-Bis(4′-hydroxyphenyl)-3-hexene
| Signal word | Danger |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07  Health Hazard GHS08  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 3,4-Bis(4′-hydroxyphenyl)-3-hexene
| InChIKey | RGLYKWWBQGJZGM-ISLYRVAYSA-N |
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