9,11-Secogorgost-5-en-9-one-3 beta,11-diol, a marine steroid from the sea whip Pseudopterogorgia hummelinkii.
The title steroid [(22R,23R,24R)-22,23-methylene-23,24-dimethyl-9,11- secocholest-5-en-9-one-3 beta,11-diol, C30H50O3], was isolated from Pseudopterogorgia hummelinkii, a Caribbean gorgonian. The cyclopropane ring in the side chain of this molecule, a feature very unusual in terrestrial steroids, has been found in several other marine steroids. The molecular structure is potentially very flexible because of the oxidative cleavage of ring C, but the two independent molecules in the crystal have quite similar overall conformations. The observed conformational differences correlate with dissimilar participation of the hydroxyl and carbonyl groups of each molecule in hydrogen bonding, which is entirely intermolecular. The crystal structure was solved by direct methods, but only with great difficulty.
Schultz
L W
LW
Department of Chemistry, Cornell University, Ithaca, New York 14853, USA.
Clardy
J
J
Lessinger
L
L
D000818:Animals; D002784:Cholesterol / Q000031:analogs & derivatives* / Q000302:isolation & purification; D003063:Cnidaria / Q000737:chemistry*; D003460:Crystallization; D015394:Molecular Structure; D013256:Steroids / Q000737:chemistry* / Q000302:isolation & purification
C093469:9,11-secogorgost-5-en-9-one-3,11-diol; D013256:Steroids; D002784:Cholesterol