4764. Hydrallostane

Nomenclature

CAS number: 516-41-6
(5α,11β)-11,17,21-Trihydroxypregnane-3,20-dione; 11β,17α,21-trihydroxyallopregnane-3,20-dione; allodihydrohydrocortisone; allopregnane-11β,17α,21-triol-3,20-dione; 4,5α-dihydrocortisol; allodihydro F.
C21H32O5; mol wt 364.48.
C 69.20%, H 8.85%, O 21.95%.

Description and references

Isoln from beef and hog adrenals: Neher, Wettstein, Helv. Chim. Acta 39, 2062 (1956). Prepn: Pataki et al., J. Biol. Chem. 195, 753 (1952); Fukushima, Daum, J. Org. Chem. 26, 520 (1961); Gould, Oliveto, US 2783254; US 2897216 (1957; 1959 to Schering); Gould, Herzog, US 2783226 (1957 to Schering); GB 742888 (1956 to Syntex).

Chemical structure

Properties

Crystals, mp 234-240°. [α]D25 +83° (acetone). Practically insol in water. Sol in methanol, acetone, chloroform.

Derivative

21-Acetate.
C23H34O6; mol wt 406.51.
C 67.96%, H 8.43%, O 23.61%.

Properties

Crystals from hexane + ethyl acetate, mp 211-213°. [α]D20 +69° (chloroform).

Derivative

21-tert-Butylacetate.
C27H42O6; mol wt 462.62.
C 70.10%, H 9.15%, O 20.75%.

Properties

Crystals from ethanol, mp 256-264° (also crystallizes as a hydrate). Sol in chloroform, oils, fats.