Research Article: (1S,5R,7R,30S)-14-De­oxy­isogarcinol

Date Published: June 01, 2012

Publisher: International Union of Crystallography

Author(s): Ranjeet Kaur, Prema G. Vasudev, Sunil K. Chattopadhyay.


The title compound, C38H50O5 {systematic name: 10-(3-hy­droxy­benzo­yl)-2,2,7,7-tetra­methyl-3,6,8-tris­(3-methyl­but-2-en­yl)-3,4,4a,5,6,7-hexa­hydro-4a,8-methano-2H-cyclo­octa­[b]pyran-9,11(8H)-dione}, is a polyisoprenylated benzophenone, isolated for the first time from the fruits of Garcinia indica during our investigation of bioactive compounds from this plant and their large-scale extraction. The relative configuration of the title compound was chosen based on comparison of its spectroscopic and optical rotation data with that of the isomorphous and isostructural compound isogarcinol, whose absolute configuration is known. The crystal packing features O—H⋯O hydrogen bonds. A Cambridge Structural Database analysis revealed that the crystal structure reported here is isomorphous and isostructural with that of isogarcinol.

Partial Text

For background information on the plant Garcinia indica and its biologically active compounds, see: Anonymous (1956 ▶); Padhye et al. (2009 ▶); Jayaprakasha & Sakariah (2002 ▶); Yamaguchi et al. (2000a ▶,b ▶); Sang et al. (2001 ▶). For related compounds, see: Krishnamurthy et al. (1981 ▶, 1982 ▶); Rao et al. (1980a ▶,b ▶); Sahu et al. (1989 ▶); Marti et al. (2009 ▶). For the isolation, purification and spectroscopic study of the title compound, see: Kaur et al. (2012 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶). For the determination of absolute configuration, see: Flack (1983 ▶); Hooft et al. (2008 ▶).




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