Date Published: February 01, 2012
Publisher: International Union of Crystallography
Author(s): Mohamed Tebbaa, Ahmed Benharref, Jean Claude Daran, Fouad Mellouki, Moha Berraho.
The title compound, C16H20O5, was synthesized from ilicic acid [2-(8-hydroxy-4a,8-dimethyldecahydronaphthalen-2-yl)acrylic acid], which was isolated from the chloroform extract of the aerial part of Inula viscose (L) Aiton [or Dittrichia viscosa (L) Greuter]. The molecule is built up from two fused six-membered rings, the epoxidized six-membered ring adopts a half-chair conformation while the other ring displays a perfect chair conformation. The crystal structure features C—H⋯O hydrogen bonds.
For medicinal background to Inula Viscosa (L) Aiton [or Dittrichia Viscosa (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Chiappini et al. (1982 ▶); Azoulay et al. (1986 ▶); Bohlman et al. (1977 ▶); Ceccherelli et al. (1988 ▶); Geissman & Toribio (1967 ▶) For the synthesis, see: Barrero et al. (2009 ▶); Tebbaa et al. (2011 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).