273. Allopregnane-3α,11β,17α,21-tetrol-20-one

Nomenclature

CAS number: 302-91-0
(3α,5α,11β)-3,11,17,21-Tetrahydroxypregnan-20-one; 3α,11β,17,21-tetrahydroxy-5α-pregnan-20-one; 3α,11β,17,21-tetrahydroxy-20-oxo-5α-pregnane; 17-(1-keto-2-hydroxyethyl)androstane-3,11,17-triol; 3α-allotetrahydrocortisol; Kendall's compound C; Reichstein's substance C; Wintersteiner's compound D.
C21H34O5; mol wt 366.49.
C 68.82%, H 9.35%, O 21.83%.

Description and 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°. [α]D21 +59.7° (c = 0.34 in methanol).

Derivative

3,21-Diacetate.
C25H38O7; mol wt 450.57.
C 66.64%, H 8.50%, O 24.86%.

Properties

Crystals, dec 204-205°. [α]D20 +73.8°; [α]20542 +90.5° (dioxane).