3609. Epiandrosterone
Nomenclature
CAS number: 481-29-8
(3β,5α)-3-Hydroxyandrostan-17-one; 3β-hydroxy-17-androstanone; isoandrosterone; 3β-androstanol-17-one; 3β-hydroxyetioallocholan-17-one. C19H30O2; mol wt 290.44.
C 78.57%, H 10.41%, O 11.02%.
Description and references
Present in normal human urine as a minor constituent, it is a less active androgen than androsterone. Synthesis: Cardwell et al., J. Chem. Soc. 1953, 361; Johnson et al., J. Am. Chem. Soc. 75, 2275 (1953); Johnson et al., ibid. 78, 6331 (1956). Review: R. I. Dorfman, R. A. Shipley, Androgens (Wiley, New York, 1956).
Derivative
dl-Form.Properties
Crystals, mp 161-162°. Gives off a musk-like odor when hot.Derivative
d-Form.Properties
Crystals from ethyl acetate + petr ether, mp 174.5°. [α]D20 +88° (in methanol). Precipitated by digitonin. Practically insol in water. Soluble in organic solvents.Derivative
Acetate.C21H32O3; mol wt 332.48.
C 75.86%, H 9.70%, O 14.44%.
Properties
Stout prisms, mp 103-104°. [α]D18 +68.5° (chloroform).Derivative
Benzoate.C26H34O3; mol wt 394.55.
C 79.15%, H 8.69%, O 12.17%.