Allopregnane-3alpha,11beta,17alpha,21-tetrol-20-one
Structural Formula Vector Image
Title: Allopregnane-3a,11b,17a,21-tetrol-20-one
CAS Registry Number: 302-91-0
CAS Name: (3a,5a,11b)-3,11,17,21-Tetrahydroxypregnan-20-one
Additional Names: 3a,11b,17,21-tetrahydroxy-5a-pregnan-20-one; 3a,11b,17,21-tetrahydroxy-20-oxo-5a-pregnane; 17-(1-keto-2-hydroxyethyl)androstane-3,11,17-triol; 3a-allotetrahydrocortisol; Kendall's compound C; Reichstein's substance C; Wintersteiner's compound D
Molecular Formula: C21H34O5
Molecular Weight: 366.49
Percent Composition: C 68.82%, H 9.35%, O 21.83%
Literature References: Isoln from adrenal cortex: Mason et al., J. Biol. Chem. 124, 459 (1938); Kuizenga, Cartland, Endocrinology 24, 526 (1939); v. Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942); v. Euw et al., ibid. 41, 1516 (1958). Prepn by hydrogenation of cortisol with rhodium: Caspi, J. Org. Chem. 24, 669 (1959); from bismethylenedioxyhydrocortisone: Fukushima, Daum, ibid. 26, 520 (1961).
Properties: Crystals from methanol, mp 244-245°. [a]D21 +59.7° (c = 0.34 in methanol).
Melting point: mp 244-245°
Optical Rotation: [a]D21 +59.7° (c = 0.34 in methanol)
 
Derivative Type: 3,21-Diacetate
Molecular Formula: C25H38O7
Molecular Weight: 450.57
Percent Composition: C 66.64%, H 8.50%, O 24.86%
Properties: Crystals, dec 204-205°. [a]D20 +73.8°; [a]20542 +90.5° (dioxane).
Optical Rotation: [a]D20 +73.8°; [a]20542 +90.5° (dioxane)

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