Androstane-3beta,11beta-diol-17-one

Title: Androstane-3b,11b-diol-17-one
CAS Registry Number: 514-17-0
CAS Name: (3b,5a,11b)-3,11-Dihydroxyandrostan-17-one
Molecular Formula: C19H30O3
Molecular Weight: 306.44
Percent Composition: C 74.47%, H 9.87%, O 15.66%
Literature References: First obtained by degradation of allopregnane-3b,11b,17a,20b,21-pentol (Reichstein's Substance A): Reichstein, Helv. Chim. Acta 19, 402 (1936), but later isolated in small quantities directly from extracts of the adrenal cortex: Reichstein, von Euw, ibid. 21, 1197 (1938); ibid. 24, 879 (1941). It is uncertain whether this substance occurs in the fresh adrenal gland; it may possibly occur by oxidation or decompn during the isolation procedure: Reichstein, Shoppee, Vitam. Horm. I, 368 (1943). Structure-activity study: S. Sassa et al., J. Biol. Chem. 254, 10011 (1979). Chromatographic studies: A. Kerebel et al., J. Chromatogr. 140, 229 (1977); J. T. Lin, E. Heftmann, ibid. 237, 215 (1982).
Properties: Needles from acetone + ether, mp 235-238°. [a]D20 +84.5° (ethanol); [a]D19 +81.3° (dioxane); [a]19545 +105° (dioxane). Precipitated by digitonin.
Melting point: mp 235-238°
Optical Rotation: [a]D20 +84.5° (ethanol); [a]D19 +81.3° (dioxane); [a]19545 +105° (dioxane)
Derivative Type: 3-Acetate
Molecular Formula: C21H32O4
Molecular Weight: 348.48
Percent Composition: C 72.38%, H 9.26%, O 18.36%
Properties: Needles from actone + ether, mp 230-231°. [a]D19 +70.5° (dioxane); [a]19546 +87.1° (dioxane).
Melting point: mp 230-231°
Optical Rotation: [a]D19 +70.5° (dioxane); [a]19546 +87.1° (dioxane)
Derivative Type: Diacetate
Molecular Formula: C23H34O5
Molecular Weight: 390.51
Percent Composition: C 70.74%, H 8.78%, O 20.49%
Properties: Crystals, mp 154-156°.
Melting point: mp 154-156°
Androstenediol Androstenedione Anecortave Acetate Anemonin Anethole