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Diethylstilbestrol

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Diethylstilbestrol Basic information
Diethylstilbestrol Chemical Properties
  • Melting point:170-172 °C(lit.)
  • Boiling point:351.51°C (rough estimate)
  • Density 1.1096 (rough estimate)
  • refractive index 1.4800 (estimate)
  • storage temp.  0-6°C
  • solubility methanol: 0.1 g/mL, clear, faintly yellow
  • pkapKa 9.02(H2O t=25 I=0.025) (Uncertain)
  • form Crystalline Powder
  • color White to almost white
  • Water Solubility PRACTICALLY INSOLUBLE
  • Merck 13,3155
  • BRN 2056095
  • Stability:Isomerizes rapidly in Benzene, Chloroform, and Ether. Keep Shielded from light.
  • CAS DataBase Reference56-53-1(CAS DataBase Reference)
  • NIST Chemistry ReferenceDiethylstilbesterol(56-53-1)
  • EPA Substance Registry SystemPhenol, 4,4'-[(1E)-1,2-diethyl- 1,2-ethenediyl]bis-(56-53-1)
Safety Information
MSDS
Diethylstilbestrol Usage And Synthesis
  • Chemical PropertiesWhite Solid
  • UsesA 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.
  • brand nameStilbestrol (Tablicaps); Stilbetin (Bristol-Myers Squibb);Distilbene;Oestro-gynedron;Stilphostrol.
  • World Health Organization (WHO)Diethylstilbestrol, a synthetic estrogen which is a stilbene derivative, was introduced into obstetric practice in the late 1940s and subsequently widely used for the treatment of threatened abortion. This use was later shown to be associated with an increased risk of vaginal cancer in the offspring which resulted in restrictive regulatory action in several countries. Diethylstilbestrol and other stilbenes remain available in many countries, however, for the treatment of certain hormone-dependent neoplasms including carcinoma of the prostate and postmenopausal breast cancer. (Reference: (WHODI) WHO Drug Information, 77.1, 16, 1977)
  • General DescriptionAt first glance, it might be surprising that synthetic nonsteroidal molecules such as diethylstilbestrol (DES) could have the same activity as estradiol or other estrogens. DES can be viewed, however, as a form of estradiol with rings B and C open and a six-carbon ring D. The activity of DES analogs was explained in 1946. It was proposed that the distance between the two DES phenol OH groups was the same as the 3-OH to 17-OH distance of estradiol; therefore, they could both fit the same receptor. Medicinal chemists have shown the OH-to-OH distance to be actually 12.1 ? in DES and 10.9 ? in estradiol. In aqueous solution, however, estradiol has two water molecules that are hydrogen bonded to the 17-OH. If one of the two water molecules is included in the distance measurement, there is a perfect fit with the two OH groups of DES. This suggests that water may have an important role for estradiol in its receptor site.
    It is now generally accepted that the estrogens must have a phenolic moiety for binding, but some investigators propose that the receptor may be flexible enough to accommodate varying distances between the two key hydroxyls. This point about estrogens needing a phenolic ring for high-affinity binding to the ER is critical. Steroids with a phenolic A ring and related phenolic compounds lack high-affinity binding to the other steroid hormone receptors.
  • General DescriptionOdorless tasteless white crystalline powder.
  • Air & Water ReactionsInsoluble in water.
  • Reactivity ProfileDiethylstilbestrol is incompatible with strong oxidizing agents, strong bases, acid chlorides and acid anhydrides .
  • Fire HazardFlash point data for Diethylstilbestrol are not available; however, Diethylstilbestrol is probably combustible.
  • Safety ProfileConfirmed carcinogen producing skin, liver, and lung tumors in exposed humans as well as uterine and other reproductive system tumors in the female offspring of exposed women. Experimental carcinogenic, neoplas tigenic, tumorigenic, and teratogenic data. A transplacental carcinogen. A human teratogen by many routes. Poison by intraperitoneal and subcutaneous routes. It causes glandular system effects by sktn contact. Human reproductive effects by ingestion: abnormalspermatogenesis; changes in testes, epididymis, and sperm duct; menstrual cycle changes or disorders; changes in female ferulity; unspecified maternal effects; developmental abnormalities of the fetal urogenital system; germ cell effects in offspring; and delayed effects in newborn. Implicated in male impotence and enlargement of male breasts. Other experimental reproductive effects. Mutation data reported. When heated to decomposition it emits acrid smoke and fumes. See also ETHINYL ESTRADIOL.
  • CarcinogenicityDiethylstilbestrol is known to be a human carcinogen based on sufficient evidence of carcinogenicity from studies in humans.
  • RegulationsEnvironmental Protection Agency (EPA)
    Comprehensive Environmental Response, Compensation, and Liability Act Reportable quantity (RQ) = 1 lb.
    Resource Conservation and Recovery Act
    Listed Hazardous Waste: Waste code for which the listing is based wholly or partly on the presence of diethylstilbestrol = U089. Listed as a hazardous constituent of waste.
    Food and Drug Administration (FDA)
    All oral and parenteral drug products containing greater than 25 mg per unit dose of diethylstilbestrol were removed from the market because they were found to be unsafe or not effective, and they may not be compounded.
    Diethylstilbestrol is prohibited from extralabel use in food-producing animals.
Diethylstilbestrol Preparation Products And Raw materials
Diethylstilbestrol(56-53-1)Related Product Information
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