3867. Etiocholanic Acid

Nomenclature

CAS number: 438-08-4
(5β,17β)-Androstane-17-carboxylic acid; aetiocholanic acid; etianic acid; etiocholane-17β-carboxylic acid.
C20H32O2; mol wt 304.47.
C 78.90%, H 10.59%, O 10.51%.

Description and references

Prepn: Wieland et al., Z. Physiol. Chem. 161, 80 (1926); Jacobs, Elderfield, J. Biol. Chem. 108, 497 (1935); Tschesche, Ber. 68, 9 (1935); Steiger, Reichstein, Helv. Chim. Acta 21, 841 (1938).

Chemical structure

Properties

Needles from glacial acetic acid; elongated leaflets from acetic acid. Sublimes at 0.002 mm press. and 160° bath temp, mp 228-229°. Insol in water; sol in pentane.

Derivative

Methyl ester.
C21H34O2; mol wt 318.49.
C 79.19%, H 10.76%, O 10.05%.

Properties

Needles from methanol, mp 99-101°.

Note

The stem name “etianic acid” was proposed by the Subcommittee on Steroid Nomenclature of the National Research Council as a replacement for “etiocholanic acid” in order to avoid the use of the same name for parent hydrocarbons of different carbon content: J. Am. Chem. Soc. 74, 2817 (1952).