274. Allopregnane-3β,11β,21-triol-20-one

Nomenclature

CAS number: 516-16-5
(3β,5α,11β)-3,11,21-Trihydroxypregnan-20-one; 3β,11β,21-trihydroxy-20-oxo-5α-pregnane; Reichstein's substance R.
C21H34O4; mol wt 350.49.
C 71.96%, H 9.78%, O 18.26%.

Description and references

Isolation from adrenal glands: Reichstein, von Euw, Helv. Chim. Acta 21, 1197 (1938); Reichstein, ibid. 1490. Partial synthesis by hydrogenation of corticosterone acetate: Pataki et al., J. Biol. Chem. 195, 751 (1952). Prepn from 3β,11β-dihydroxyalloetiocholanic acid: Lardon, Reichstein, Helv. Chim. Acta 37, 443 (1954); from hydrocortisone: Mancera et al, J. Am. Chem. Soc. 77, 5669 (1955); from 3β,21-diacetoxy-17(20)-allopregnene + osmium tetroxide and triethylamine oxide peroxide: Schneider, Hanze, US 2769823 (1956 to Upjohn).

Properties

Needles from alc, mp 202-204°. [α]D +110° (ethanol).

Derivative

3,21-Diacetate.
C25H38O6; mol wt 434.57.
C 69.10%, H 8.81%, O 22.09%.

Properties

Crystals from acetone + ether, mp 170-172°. [α]D22 +82.5° (c = 1.38 in dioxane); [α]D20 +101° (acetone).