6898-97-1

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;4,4'-Hex-3-ene-3,4-diyldiphenol;DES;Diethylstilbestrol;3,4-Bis(4-hydroxyphenyl)-3-hexene
• CAS NO: 6898-97-1
• Molecular Formula: C₁₈H₂₀O₂
• Molecular Weight: 268.35
• EINECS: 200-278-5
• Product Categories: Stilbenes;Acyclic;Alkenes;Bioactive Small Molecules;Building Blocks;Cell Biology;Chemical Synthesis;D-DIF;Organic Building Blocks
• Mol File: 6898-97-1.mol
• Article Data: 4

Chemical Properties

• Melting Point: 170-172 °C(lit.)
• Boiling Point: 407.102 °C at 760 mmHg
• Flash Point: 186.946 °C
• Appearance: /
• Density: 1.108 g/cm³
• Vapor Pressure: 3.29E-07mmHg at 25°C
• Refractive Index: 1.603
• Solubility: soluble in Methanol
• PKA: 9.27±0.15(Predicted)
• Water Solubility: PRACTICALLY INSOLUBLE
• Merck: 14,3129
• CAS DataBase Reference: Diethylstilbestrol(CAS DataBase Reference)
• NIST Chemistry Reference: Diethylstilbestrol(6898-97-1)
• EPA Substance Registry System: Diethylstilbestrol(6898-97-1)

Safety Data

• Hazard Codes: T,N
• 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
• Hazardous Substances Data: 6898-97-1(Hazardous Substances Data)

Usage

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.

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-α,β-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).

InChI:InChI=1/C18H20O2/c1-3-17(13-5-9-15(19)10-6-13)18(4-2)14-7-11-16(20)12-8-14/h5-12,19-20H,3-4H2,1-2H3/b18-17-

Upstream product

• 70-70-2 4-hydroxypropiophenone 
• 121-97-1 4-Methoxypropiophenone 
• 4646-94-0 2-(4-methoxyphenyl)-n-butanoic acid 
• 4390-94-7 1,2-bis(4-methoxyphenyl)butanone 
• 120-44-5 1,4-di(4-methoxyphenyl)ethanone 
• 752225-73-3 C₂₀H₂₄O₂ 
• 7773-34-4 diethylstilbestrol dimethyl ether 

Downstream Products

• 67566-78-3 3,3'-<α,β-Diethyl-4,4'-stilbendiylbis-(oxycarbonyl)>-dipropionsaeure 
• 106424-48-0 Diaethylstilboestrol-bis-β-(p-methoxyphenyl)-propionat 
• 106424-56-0 Diaethylstilboestrol-bis-β-(p-propoxyphenyl)-propionat 
• 106990-86-7 Diaethylstilboestrol-bis-β-(p-butoxyphenyl)-propionat 
• 106990-87-8 Diaethylstilboestrol-bis-β-(p-isobutoxyphenyl)-propionat 
• 106301-64-8 Diaethylstilboestrol-bis-β-(p-isopropoxyphenyl)-propionat 
• 107117-00-0 Diaethylstilboestrol-bis-β-(p-hexoxyphenyl)-propionat 
• 106570-08-5 Diaethylstilboestrol-bis-β-(p-heptoxyphenyl)-propionat 
• 107085-21-2 Diaethylstilboestrol-bis-β-(p-decyloxyphenyl)-propionat 
• 107086-56-6 Diaethylstilboestrol-bis-β-(p-dodecyloxyphenyl)-propionat 
• 88181-16-2 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 
• 13425-53-1 C₁₈H₂₂O₈P₂ 

Relevant articles and documents

Anti-proliferative activities of flavone-estradiol Stille-coupling adducts and of indanone-based compounds obtained by SnCl4/Zn-catalysed McMurry cross-coupling reactions

We described the synthesis of flavone-estradiol adducts and indanophen based tamoxifen analogs using a novel SnCl4-Zn reagent via a McMurry cross-coupling reaction and their anti-proliferative evaluation against human cervical cancer cell lines (HeLa) and human breast cancer cell lines (MCF-7 and MDA-MB-231). A library of 32 tamoxifen analogs was synthesized using indanone and propiophenone derivatives and evaluated for anti-proliferative activities. Among them, compounds 3ac, 3ad, 3ae and 3ao exhibited better anti-proliferative potencies (IC50 2.13-3.81 μM) than the drug doxorubicin (IC50 50 2.85 ± 0.17 μM and 2.42 ± 0.23 μM; 3.64 ± 0.28 μM and 2.93 ± 0.14 μM) against breast cancer cells (MCF-7 and MDA-MB-231) respectively and IC50 2.17 ± 0.18 μM and 2.56 ± 0.32 μM against cervical cancer cells (HeLa) respectively than the standard drug. However, compounds 6ac, 6ae, 6af and 6ag showed moderate activity (IC50 10 μM). The structure-activity relationship analysis revealed that the optimal combination of side chains at the para-position of propiophenone and fluoro substituent on the indanone moiety enhanced the anti-proliferative activities of tamoxifen analogs.

Human insulin analogues

The present invention relates to novel human insulin analogues exhibiting a low ability to associate in solution, a method for the preparation of such insulin analogues, insulin preparations containing the human insulin analogues of the invention and a method of treating Diabetes Mellitus using these human insulin analogues.