Title: Epiandrosterone
CAS Registry Number: 481-29-8
CAS Name: (3b,5a)-3-Hydroxyandrostan-17-one
Synonyms: 3b-hydroxy-17-androstanone; isoandrosterone; 3b-androstanol-17-one; 3b-hydroxyetioallocholan-17-one
Molecular Formula: C19H30O2
Molecular Weight: 290.44
Percent Composition: C 78.57%, H 10.41%, O 11.02%
Literature 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 Type: dl-Form
Properties: Crystals, mp 161-162°. Gives off a musk-like odor when hot.
Melting point: mp 161-162°
Derivative Type: d-Form
Properties: Crystals from ethyl acetate + petr ether, mp 174.5°. [a]D20 +88° (in methanol). Precipitated by digitonin. Practically insol in water. Soluble in organic solvents.
Melting point: mp 174.5°
Optical Rotation: [a]D20 +88° (in methanol)
Derivative Type: Acetate
Molecular Formula: C21H32O3
Molecular Weight: 332.48
Percent Composition: C 75.86%, H 9.70%, O 14.44%
Properties: Stout prisms, mp 103-104°. [a]D18 +68.5° (chloroform).
Melting point: mp 103-104°
Optical Rotation: [a]D18 +68.5° (chloroform)
Derivative Type: Benzoate
Molecular Formula: C26H34O3
Molecular Weight: 394.55
Percent Composition: C 79.15%, H 8.69%, O 12.17%
Properties: Crystals, mp 210-212°.
Melting point: mp 210-212°
