9210. Tetrahydrocortisone

Nomenclature

CAS number: 53-05-4
(3α,5β)-3,17,21-Trihydroxypregnane-11,20-dione; 3α,17α,21-pregnanetriol-11,20-dione; 11,20-pregnanedione-3α,17α,21-triol; THE.
C21H32O5; mol wt 364.48.
C 69.20%, H 8.85%, O 21.95%.

Description and references

A normal mammalian metabolite of cortisone: Schneider, J. Biol. Chem. 183, 365 (1950). Prepn by microbial reduction using a Streptomyces sp.: Barkemeyer et al., Appl. Microbiol. 8, 237 (1960). Prepn of the triacetate: GB 737291 (1955 to Merck & Co.). Prepn of the 21-acetate: Julian et al., US 2752339 (1956 to Glidden).

Chemical structure

Properties

Crystals from ethyl acetate, mp 190°. [α]D25 +85.5° (abs ethanol).

Derivative

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

Properties

Crystals from acetone, mp 227°.

Derivative

Triacetate.
C27H38O8; mol wt 490.59.
C 66.10%, H 7.81%, O 26.09%.

Properties

Crystals from methanol, mp 150-152°; solvated crystals from ethyl acetate, mp 112-118°.