12-00274. Allopregnane-3β,11β,17α,20β,21-pentol [Archived]

Nomenclature

CAS number: 516-39-2
5α-Pregnane-3β,11β,17,20β,21-pentol; 3β,11β,17,20β,21-pentahydroxy-5α-pregnane; 17-(1,2-dihydroxyethyl)androstane-3,11,17-triol; Kendall's compound D; Reichstein's substance A; Wintersteiner's compound A.
C21H36O5; mol wt 368.51.
C 68.44%, H 9.85%, O 21.71%.

Description and references

Occurs in adrenal cortex: Mason et al., J. Biol. Chem. 114, 613 (1936). Prepn from 21-acetoxy-3β,17α-dihydroxy-5α-pregnane-11,20-dione + lithium aluminum hydride: Klyne, Ridley, J. Chem. Soc. 1956, 4825; by hydrogenation of cortisol with platinum oxide: Caspi, J. Org. Chem. 24, 669 (1959).

Properties

Crystals from methanol, mp 159-163°, resolidifies and mp 215-216°. [α]D22 +9.8° (c = 0.56 in methanol).

Status

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