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.
Erabutoxins Erbium Sulfate Erdin Erdosteine Ergocornine

Equilenin
Equilenin.svg
Systematic (IUPAC) name
3-hydroxy-13-methyl-12,14,15,16-tetrahydro-
11H-cyclopenta[a]phenanthren-17-one
Clinical data
Legal status  ?
Identifiers
CAS number 517-09-9 N
ATC code  ?
PubChem CID 444865
DrugBank DB03515
ChemSpider 392668 YesY
KEGG C14303 YesY
ChEMBL CHEMBL225546 YesY
Chemical data
Formula C18H18O2 
Mol. mass 266.339 g/mol
 N (what is this?)  (verify)

Equilenin is an estrogenic steroid hormone obtained from the urine of pregnant mares. It is used as one of the components in Premarin. It was the first complex natural product to be successfully, fully synthesized in 1940 by Alfred L. Wilds.