Allopregnane-3beta,11beta,17alpha,21-tetrol-20-one

Title: Allopregnane-3b,11b,17a,21-tetrol-20-one
CAS Registry Number: 651-43-4
CAS Name: 3b,11b,17,21-Tetrahydroxy-5a-pregnan-20-one
Additional Names: 3b,11b,17,21-tetrahydroxy-20-oxo-5a-pregnane; Reichstein's substance V
Molecular Formula: C21H34O5
Molecular Weight: 366.49
Percent Composition: C 68.82%, H 9.35%, O 21.83%
Literature References: Isoln from adrenal cortex: von Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942). Prepn from 5a-pregnan-3b-ol-11,20-dione: Chamberlin, Chemerda, J. Am. Chem. Soc. 77, 1221 (1955); by hydrogenation of cortisol with rhodium: Caspi, J. Org. Chem. 24, 669 (1959); from bismethylenedioxyhydrocortisone: Fukushima, Daum, ibid. 26, 520 (1961).
Properties: Needles from dilute methanol, decomp 220-225°. [a]D13 +50.7° (c = 0.8672 in dioxane).
Optical Rotation: [a]D13 +50.7° (c = 0.8672 in dioxane)
Derivative Type: 3,21-Diacetate
Molecular Formula: C25H38O7
Molecular Weight: 450.57
Percent Composition: C 66.64%, H 8.50%, O 24.86%
Properties: Flat prisms from acetone-ether, decomp 225-227°. [a]D18 +62.6° (c = 1.101 in dioxane).
Optical Rotation: [a]D18 +62.6° (c = 1.101 in dioxane)
Status: This monograph has been retired and is no longer subject to revision or update.
Allopregnane-3beta,11beta,21-triol-20-one Allopregnane-3beta,17alpha,20alpha-triol Allopregnane-3beta,17alpha,20beta,21-tetrol Allopregnane-3beta,17alpha,20beta-triol Allopregnane-3beta,17alpha,21-triol-11,20-dione