3642. Equilenin

Nomenclature

CAS number: 517-09-9
3-Hydroxyestra-1,3,5,7,9-pentaen-17-one; 11,12,13,14,15,16-hexahydro-3-hydroxy-13-methyl-17H-cyclopenta[a]phenanthren-17-one; 1,3,5:10,6,8-estrapentaen-3-ol-17-one.
C18H18O2; mol wt 266.33.
C 81.17%, H 6.81%, O 12.01%.

Description and references

Estrogenic steroidal hormone isolated from urine of pregnant mares: Girard et al., Compt. Rend. 195, 981 (1932). Occurs naturally in the d-form. Not found in human urine. Component of Conjugated Estrogenic Hormones, q.v. Isoln by chromatography: Duschinsky, Lederer, Bull. Soc. Chim. Biol. 17, 1534 (1935). Total synthesis: Bachmann et al., J. Am. Chem. Soc. 61, 974 (1939); 62, 824 (1940); Johnson et al., ibid. 67, 2274 (1945); 69, 2942 (1947); 72, 505 (1950); Hughes, Smith, Chem. Ind. (London) 1960, 1022; Bailey et al., Chem. Commun. 1967, 1253; Stein et al., Tetrahedron 26, 1917 (1970). Synthesis from estrone: Corbellini et al., Farmaco Ed. Sci. 19, 913 (1964); O. N. Minailova et al., Zh. Obshch. Khim. 49, 2633 (1979); A. R. Daniewski, T. Kowalczyk-Przewloka, Tetrahedron Lett. 1982, 2411. Review of synthetic studies: Taub, “Naturally Occurring Aromatic Steroids” in The Total Synthesis of Natural Products vol. 2, J. ApSimon, Ed. (John Wiley & Sons, New York, 1973) pp 642-663.

Chemical structure

Properties

Needles from dil alc, mp 258-259°. Sublimes at 170-180° at 0.01 mm Hg. [α]D16 +87° (12.8 mg made up to 1.8 ml in dioxane). uv max (ethanol): 231, 270, 282, 292, 325, 340 nm. Soly/100 ml alcohol 0.63 (18°); 2.5 g (boiling).

Derivative

Acetate.
C20H20O3; mol wt 308.37.
C 77.90%, H 6.54%, O 15.57%.

Properties

mp 156-157°.

Derivative

Benzoate.
C25H22O3; mol wt 370.44.
C 81.06%, H 5.99%, O 12.96%.

Properties

mp 222-223° (vac).

Derivative

Methyl ether.
C19H20O2; mol wt 280.36.
C 81.40%, H 7.19%, O 11.41%.

Properties

Needles from alc, mp 197-198°; mp 193-194° (vac).

Therapeutic Category

Estrogen.

Keywords

Estrogen; Steroidal