12-00277. Allopregnane-3β,11β,17α,21-tetrol-20-one [Archived]

Nomenclature

CAS number: 651-43-4
3β,11β,17,21-Tetrahydroxy-5α-pregnan-20-one; 3β,11β,17,21-tetrahydroxy-20-oxo-5α-pregnane; Reichstein's substance V.
C21H34O5; mol wt 366.49.
C 68.82%, H 9.35%, O 21.83%.

Description and references

Isoln from adrenal cortex: von Euw, Reichstein, Helv. Chim. Acta 25, 988 (1942). Prepn from 5α-pregnan-3β-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°. [α]D13 +50.7° (c = 0.8672 in dioxane).

Derivative

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

Properties

Flat prisms from acetone-ether, decomp 225-227°. [α]D18 +62.6° (c = 1.101 in dioxane).

Status

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