Crystal Structure of Tetrahymanol Hemihydrate

David A. Langs, William L. Duax, H. L. Carrell, Helen Berman, Eliahu Caspi

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

The crystal structure of a hemihydrate of the pentacyclic triterpenoid tetrahymanol, C30H52O·1/2H2O [monoclinic, P21, a = 7.417 (1) Å, b = 11.438 (2), c = 30.248 (4), β = 91.95°, Z = 4,R = 0.076] has been determined. Steric overcrowding warps the gross conformation of the two molecules in the asymmetric unit and generates unusually long carbon-carbon single bonds. The observed weakening of the C8–C14 bond, whose average length is 1.61 Å, is consistent with its scission observed in mass spectral experiments. Although the molecular skeleton possesses rotational symmetry, the observed conformations are markedly asymmetric, appear to be independent of the hydroxyl moiety, and suggest the presence of conformational isomers in solution.

Original languageEnglish (US)
Pages (from-to)2134-2137
Number of pages4
JournalJournal of Organic Chemistry
Volume42
Issue number12
DOIs
StatePublished - Jun 1 1977
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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