Diethylstilbestrol
Title: Diethylstilbestrol
CAS Registry Number: 56-53-1
CAS Name: 4,4¢[(1E)-1,2-Diethyl-1,2-ethenediyl]bisphenol
Additional Names: (E)-a,-diethyl-4,4¢-stilbenediol; (E)-3,4-bis(4-hydroxyphenyl)-3-hexene; 4,4¢-dihydroxy-a,b-diethylstilbene; stilbestrol; stilboestrol; DES
Trademarks: Apstil (APS); Cyren A (Bayer); Distilbène (Gerda); Stilbetin (BMS)
Molecular Formula: C18H20O2
Molecular Weight: 268.35
Percent Composition: C 80.56%, H 7.51%, O 11.92%
Literature References: Synthetic, nonsteroidal estrogen. Prepn: E. C. Dodds et al., Nature 141, 247 (1938); eidem, Proc. R. Soc. London Ser. B 127, 140 (1939). Prepn of ethers: E. E. Reid, E. Wilson, J. Am. Chem. Soc. 64, 1625 (1942). Review of early literature: U. V. Solmssen, Chem. Rev. 37, 481-598 (1945). HPLC determn in plasma and urine: A. T. Rhys Williams et al., J. Chromatogr. 235, 461 (1982). Clinical trial in breast cancer: A. C. Carter et al., J. Am. Med. Assoc. 237, 2079 (1977); in prostate cancer: C. J. Nickel. A. Morales, Can. J. Surg. 26, 434 (1983). Review of metabolism: M. Metzler, Crit. Rev. Biochem. 10, 171-212 (1981). Review of toxicology and use as a growth promotant in livestock: K. E. McMartin et al., J. Environ. Pathol. Toxicol. 1, 279-313 (1978). Book: Developmental Effects of Diethylstilbestrol (DES) in Pregnancy, A. L. Herbst, H. A. Bern, Eds. (Thieme-Verlag, New York, 1981) 203 pp. Comprehensive description: A. A. Al-Badr, A. G. Mekkawi, Anal. Profiles Drug Subs. 19, 145-192 (1990).
Properties: Small plates from benzene, mp 169-172°. uv max (0.1N NaOH): 259 nm (E1%1cm 764). Almost insol in water. Sol in alcohol, ether, chloroform, fatty oils, dil hydroxides.
Melting point: mp 169-172°
Absorption maximum: uv max (0.1N NaOH): 259 nm (E1%1cm 764)
 
Derivative Type: Diphosphate see Fosfestrol
 
Derivative Type: Dipropionate
CAS Registry Number: 130-80-3
Trademarks: Cyren B (Bayer); Dibestil (Sterling Winthrop)
Molecular Formula: C24H28O4
Molecular Weight: 380.48
Percent Composition: C 75.76%, H 7.42%, O 16.82%
Properties: Plates from methanol, mp 104°. Sol in organic solvents and in vegetable oils.
Melting point: mp 104°
 
Derivative Type: Dimethyl ether see Dimestrol
 
Derivative Type: Monomethyl ether
CAS Registry Number: 18839-90-2
CAS Name: 4-[(1E)-1-Ethyl-2-(4-methoxyphenyl)-1-butenyl]phenol
Additional Names: mestilbol
Molecular Formula: C19H22O2
Molecular Weight: 282.38
Percent Composition: C 80.81%, H 7.85%, O 11.33%
Properties: Crystals from benzene + petr ether, mp 116-117.5°.
Melting point: mp 116-117.5°
 
CAUTION: Diethylstilbestrol is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-98.
Therap-Cat: Antineoplastic (hormonal).
Keywords: Estrogen; Nonsteroidal; Antineoplastic (Hormonal); Estrogens.

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