12-04563. Gratiogenin [Archived]

Nomenclature

CAS number: 7067-16-5
(3β,9β,10α,24S)-20,24-Epoxy-3,25-dihydroxy-9-methyl-19-norlanost-5-en-11-one.
C30H48O4; mol wt 472.70.
C 76.23%, H 10.24%, O 13.54%.

Description and references

Tetracyclic triterpene closely related to the cucurbitacins. Prepd by hydrolysis of gratioside: Retzlaff, Arch. Pharm. 240, 561 (1902). Structural studies: Tschesche, Heesch, Ber. 85, 1067 (1952). Revised structure: Tschesche et al., Ann. 674, 196 (1964).

Chemical structure

Properties

Clusters of needles from methanol or ethanol, mp 191-196°. [α]D20 +168° (c = 1.193 in chloroform); [α]D20 +151° (c = 0.863 in methanol). Also reported as mp 202-203°. [α]D25 +175 ± 3° (chloroform), (Tschesche, 1964). Freely sol in methanol, ethanol, chloroform, acetone, pyridine. Practically insol in water, ether, petr ether.

Status

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