12-00279. Allopregnane-3β,17α,20β-triol [Archived]

Nomenclature

CAS number: 520-86-5
5α-Pregnane-3β,17,20β-triol; 3β,17,20β-trihydroxy-5α-pregnane; 17-(1-hydroxyethyl)androstane-3,17-diol; Reichstein's substance J.
C21H36O3; mol wt 336.51.
C 74.95%, H 10.78%, O 14.26%.

Description and references

Isoln from adrenal cortex: Reichstein, Helv. Chim. Acta 19, 1126 (1936); Steiger, Reichstein, ibid. 21, 546 (1938). Prepn from 3β-acetoxy-16α,17α-oxido-20-oxo-5-allopregnane: Plattner et al., ibid. 31, 2210 (1948); GB 665254 (1952 to Ciba); from 3β-acetoxy-17α-hydroxyallopregnan-20-one: Fukushima, Meyer, J. Org. Chem. 23, 174 (1958).

Properties

Rhomboid needles from dil acetone, mp 216-217°. Sublimes in high vacuum. [α]D20 7.9° (c = 1.77 in abs alc).

Derivative

3,20-Diacetate.
C25H40O5; mol wt 420.58.
C 71.39%, H 9.59%, O 19.02%.

Properties

Crystals from pentane, mp 161-162°. [α]D20 +24.6° (c = 2.11 in acetone).

Status

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