Allopregnane-3beta,17alpha,21-triol-20-one

Title: Allopregnane-3b,17a,21-triol-20-one
CAS Registry Number: 516-47-2
CAS Name: 3b,17,21-Trihydroxy-5a-pregnan-20-one
Additional Names: 3a,17,21-trihydroxy-20-oxo-5a-pregnane; Reichstein's substance P
Molecular Formula: C21H34O4
Molecular Weight: 350.49
Percent Composition: C 71.96%, H 9.78%, O 18.26%
Literature References: Isoln from adrenal glands: Steiger, Reichstein, Helv. Chim. Acta 21, 546 (1938); Reichstein, Gatzi, ibid. 1185. Partial synthesis from cholesterol: Reichstein, von Euw, ibid. 24, 401 (1941). Prepn from allopregnan-3b-ol-20-one: Rosenkranz et al., J. Am. Chem. Soc. 72, 4081 (1950); from 3b-acetoxy-21-bromo-17a-hydroxy-2-oxoallopregnane: Kaufmann et al., US 2596562 (1952 to Syntex).
Properties: Pointed needles from abs ethanol, decomp 230-239°. [a]D20 +48.0° (c = 0.938 in abs ethanol). Freely sol in alcohol, acetone. Sparingly sol in ether, water.
Optical Rotation: [a]D20 +48.0° (c = 0.938 in abs 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 benzene, mp 208-210°. [a]D20 +41.5° (chloroform).
Melting point: mp 208-210°
Optical Rotation: [a]D20 +41.5° (chloroform)
Status: This monograph has been retired and is no longer subject to revision or update.
Allopregnane-3beta,17alpha-diol-20-one Allopregnane-3beta,20alpha-diol Allopregnane-3beta,20beta-diol Allopregnane-3beta,21-diol-11,20-dione Allopurinol