2542. Cortolone

Nomenclature

CAS number: 516-42-7
(3α,5β,20S)-3,17,20,21-Tetrahydroxypregnan-11-one; 3α,17α,20α,21-pregnanetetrol-11-one.
C21H34O5; mol wt 366.49.
C 68.82%, H 9.35%, O 21.83%.

Description and references

Isolated from human urine after administration of cortisone, hydrocortisone or ACTH: D. K. Fukushima et al., J. Biol. Chem. 212, 449 (1955). Synthesis: L. H. Sarett, J. Am. Chem. Soc. 71, 1169 (1949); A. H. Soloway et al., ibid. 76, 2941 (1954).

Chemical structure

Properties

Crystals from acetone, mp 208-209°. [α]D25 +44° (c = 0.5 in ethanol); also reported as [α]D28 +34.2° (ethanol).

Derivative

3,20,21-Triacetate.

Nomenclature

CAS number: 2638-46-2
C27H40O8; mol wt 492.60.
C 65.83%, H 8.18%, O 25.98%.

Properties

Crystals from methanol, mp 214-216° (Fukushima); also reported as mp 213-214° (Sarett). [α]D28 +28° (ethanol); also reported as [α]D25 +18° (c = 1 in acetone).