3211. Dimestrol

Nomenclature

CAS number: 130-79-0
1,1′-[(1E)-1,2-Diethyl-1,2-ethenediyl]bis[4-methoxybenzene]; (E)-α,α′-diethyl-4,4′-dimethoxystilbene; stilbestrol dimethyl ether; (E)-3,4-bis(p-methoxyphenyl)-3-hexene; (E)-3,4-dianisyl-3-hexene.
C20H24O2; mol wt 296.40.
C 81.04%, H 8.16%, O 10.80%.

Description and references

Nonsteroidal synthetic estrogen; dimethyl ether of diethylstilbestrol, q.v. Prepn: Dodds et al., Nature 142, 211, 247 (1938); Reid, Wilson, J. Am. Chem. Soc. 64, 1625 (1942); Sisido, Nozaki, J. Am. Chem. Soc. 70, 777 (1948). Improved stereospecific prepn: T. Hiyama, H. Nozaki, Bull. Chem. Soc. Jpn. 46, 2248 (1973). Crystal structure: G. Ruban, P. Luger, Acta Crystallogr. B31, 2658 (1975). Biological activities: Y. Inamori et al., Chem. Pharm. Bull. 33, 4478 (1985). Review and bibliography: Solmssen, Chem. Rev. 37, 481 (1945).

Chemical structure

Properties

Crystals from petr ether, mp 124°. Less sol than the monomethyl ether, mestilbol. Practically insol in water. Sol in alcohol; freely sol in acetone, ether; also sol in dil aq or alcoholic solns of alkali hydroxides and in vegetable oils.