Allopregnane-3beta,11beta,21-triol-20-one

Title: Allopregnane-3b,11b,21-triol-20-one
CAS Registry Number: 516-16-5
CAS Name: (3b,5a,11b)-3,11,21-Trihydroxypregnan-20-one
Additional Names: 3b,11b,21-trihydroxy-20-oxo-5a-pregnane; Reichstein's substance R
Molecular Formula: C21H34O4
Molecular Weight: 350.49
Percent Composition: C 71.96%, H 9.78%, O 18.26%
Literature References: Isolation from adrenal glands: Reichstein, von Euw, Helv. Chim. Acta 21, 1197 (1938); Reichstein, ibid. 1490. Partial synthesis by hydrogenation of corticosterone acetate: Pataki et al., J. Biol. Chem. 195, 751 (1952). Prepn from 3b,11b-dihydroxyalloetiocholanic acid: Lardon, Reichstein, Helv. Chim. Acta 37, 443 (1954); from hydrocortisone: Mancera et al, J. Am. Chem. Soc. 77, 5669 (1955); from 3b,21-diacetoxy-17(20)-allopregnene + osmium tetroxide and triethylamine oxide peroxide: Schneider, Hanze, US 2769823 (1956 to Upjohn).
Properties: Needles from alc, mp 202-204°. [a]D +110° (ethanol).
Melting point: mp 202-204°
Optical Rotation: [a]D +110° (ethanol)
Derivative Type: 3,21-Diacetate
Molecular Formula: C25H38O6
Molecular Weight: 434.57
Percent Composition: C 69.10%, H 8.81%, O 22.09%
Properties: Crystals from acetone + ether, mp 170-172°. [a]D22 +82.5° (c = 1.38 in dioxane); [a]D20 +101° (acetone).
Melting point: mp 170-172°
Optical Rotation: [a]D22 +82.5° (c = 1.38 in dioxane); [a]D20 +101° (acetone)
Allopregnane-3beta,17alpha,20alpha-triol Allopregnane-3beta,17alpha,20beta,21-tetrol Allopregnane-3beta,17alpha,20beta-triol Allopregnane-3beta,17alpha,21-triol-11,20-dione Allopregnane-3beta,17alpha,21-triol-20-one