Equilenin
Title: Equilenin
CAS Registry Number: 517-09-9
CAS Name: 3-Hydroxyestra-1,3,5,7,9-pentaen-17-one
Additional Names: 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
Molecular Formula: C18H18O2
Molecular Weight: 266.33
Percent Composition: C 81.17%, H 6.81%, O 12.01%
Literature 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.
Properties: Needles from dil alc, mp 258-259°. Sublimes at 170-180° at 0.01 mm Hg. [a]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).
Melting point: mp 258-259°
Optical Rotation: [a]D16 +87° (12.8 mg made up to 1.8 ml in dioxane)
Absorption maximum: uv max (ethanol): 231, 270, 282, 292, 325, 340 nm
 
Derivative Type: Acetate
Molecular Formula: C20H20O3
Molecular Weight: 308.37
Percent Composition: C 77.90%, H 6.54%, O 15.57%
Properties: mp 156-157°.
Melting point: mp 156-157°
 
Derivative Type: Benzoate
Molecular Formula: C25H22O3
Molecular Weight: 370.44
Percent Composition: C 81.06%, H 5.99%, O 12.96%
Properties: mp 222-223° (vac).
Melting point: mp 222-223° (vac)
 
Derivative Type: Methyl ether
Molecular Formula: C19H20O2
Molecular Weight: 280.36
Percent Composition: C 81.40%, H 7.19%, O 11.41%
Properties: Needles from alc, mp 197-198°; mp 193-194° (vac).
Melting point: mp 197-198°; mp 193-194° (vac)
 
Therap-Cat: Estrogen.
Keywords: Estrogen; Steroidal.

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