12-00280. Allopregnane-3β,17α,21-triol-11,20-dione [Archived]

Nomenclature

CAS number: 516-45-0
3β,17,21-Trihydroxy-5α-pregnane-11,20-dione; 3β,17,21-trihydroxy-11,20-dioxo-5α-pregnane; 17-(1-keto-2-hydroxyethyl)androstane-3,17-diol-11-one; Kendall's compound G; Reichstein's substance D; Wintersteiner's compound B.
C21H32O5; mol wt 364.48.
C 69.20%, H 8.85%, O 21.95%.

Description and references

Occurs in adrenal cortex: Kuizenga, Cartland, Endocrinology 24, 526 (1939); von Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942); 41, 1516 (1958). Prepn by reduction of allopregnane-17α,21-diol-3,11,20-trione: Kaufmann, Pataki, Experientia 7, 260 (1951); from 5α-pregnan-3β-ol-11,20-dione: Chamberlin, Chemerda, J. Am. Chem. Soc. 77, 1221 (1955).

Properties

Crystals from abs alc, mp 238-242°. [α]D20 +61.8° (c = 1.07 in dioxane).

Derivative

3,21-Diacetate.
C25H36O7; mol wt 448.55.
C 66.94%, H 8.09%, O 24.97%.

Properties

Crystals, mp 223-224°. [α]D20 +72.3° (dioxane).

Status

This monograph has been retired and is no longer subject to revision or update.