22610-99-7

Basic information

• Product Name: CIS-DIETHYLSTILBESTROL
• Synonyms: (z)-4,4’-(1,2-diethyl-1,2-ethylenediyl)bisphenol;alpha’-diethyl-4’-stilbenedio(z)-alpha;cis-alpha,alpha’-diethyl-4,4’-stilbenediol;cis-des;cis-diethylstilbesterol;(Z)-DES;(Z)-α,β-Diethyl-4,4'-stilbenediol;4,4'-[(Z)-1,2-Diethyl-1,2-ethenediyl]bisphenol
• CAS NO: 22610-99-7
• Molecular Formula: C₁₈H₂₀O₂
• Molecular Weight: 268.3502
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 22610-99-7.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 407.1°Cat760mmHg
• Flash Point: 186.9°C
• Appearance: /
• Density: 1.107g/cm³
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Stability: Isomerizes rapidly in Benzene, Chloroform, and Ether. Keep Shielded from light.
• CAS DataBase Reference: CIS-DIETHYLSTILBESTROL(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-DIETHYLSTILBESTROL(22610-99-7)
• EPA Substance Registry System: CIS-DIETHYLSTILBESTROL(22610-99-7)

Safety Data

• Hazardous Substances Data: 22610-99-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 22610-99-7 differently. You can refer to the following data:
1. A synthetic, nonsteroidal estrogen. Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.
2. A synthetic, nonsteroidal estrogen.Recomended solvents are DMSO, DMF and ethanol, even in these solvents do not store in solution for any prolonged period of time.

Upstream product

• 70-70-2 4-hydroxypropiophenone 
• 2297-48-5 C₁₈H₂₂O₃ 
• 18922-12-8 4,4-Bis(p-acetoxyphenyl)-3-hexanone 
• 18922-13-9 diethylstilbesterol pinacolone 
• 130-80-3 3,4-bis-(4-propionyloxy-phenyl)-hex-3c-ene 
• 7664-41-7 ammonia 
• 56-53-1 diethylstilbestrol 
• 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

• 56-53-1 diethylstilbestrol 
• 67566-78-3 3,3'-<α,β-Diethyl-4,4'-stilbendiylbis-(oxycarbonyl)>-dipropionsaeure 
• 88181-17-3 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 
• 13425-53-1 C₁₈H₂₂O₈P₂ 
• 88181-16-2 4,4'-bis of α,α'-diethyl-4,4'-stilbenediol 
• 107086-56-6 Diaethylstilboestrol-bis-β-(p-dodecyloxyphenyl)-propionat 
• 107085-21-2 Diaethylstilboestrol-bis-β-(p-decyloxyphenyl)-propionat 
• 106570-08-5 Diaethylstilboestrol-bis-β-(p-heptoxyphenyl)-propionat 
• 107117-00-0 Diaethylstilboestrol-bis-β-(p-hexoxyphenyl)-propionat 
• 106301-64-8 Diaethylstilboestrol-bis-β-(p-isopropoxyphenyl)-propionat 
• 106990-87-8 Diaethylstilboestrol-bis-β-(p-isobutoxyphenyl)-propionat 

Relevant articles and documents

NON-ESTROGENIC METABOLITES OF DIETHYLSTILBESTROL PRODUCED BY PROSTAGLANDIN SYNTHASE MEDIATED METABOLISM

Incubation of trans-diethylstilbestrol (E-DES) with prostaglandin synthase (PGS) in vitro leads to the formation of the metabolites cis,cis-dienestrol (Z,Z-DIES) and cis-diethylstilbestrol (Z-DES) which have considerably decreased estrogenic activity compared to their parent compound.Incubations of (14C)-E-DES with PGS in the presence of arachidonic acid (AA) predominantly catalyze formation of the oxidative metabolite Z,Z-DIES, accompanied by the formation of protein bound radioactivity.Inhibition of peroxidative metabolism through addition of indomethacin or absence of AA favors isomerization of E-DES to Z-DES without concomitant formation of protein bound radioactivity.Isomerization is inhibited by phenidone (1-phenyl-3-pyrazolidone).Since PGS activity is present in uterine tissue, these pathways may play a role in the metabolism of DES in its target tissue.

Synthesis and biological evaluation of stilbene-based pure estrogen antagonists

The nonsteroidal estrogen diethylstilbestrol can be converted into potent antiestrogens devoid of agonist activity by introduction of side chains with appropriate functional groups. Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists.

STERICALLY-DRIVEN ANHYDRIDE FORMATION

Oxidative coupling of highly substituted carboxylic acid dianions affords hindered succinic acid derivatives which undergo facile intramolecular anhydride formation.A novel, but low yield, synthetic sequence converts 4'-methoxypropiophenone into diethylstilbestrol.