Research Article: rac-[3-Hydroxy-6,9-dimethyl-6-(4-methylpent-3-en-1-yl)-6a,7,8,9,10,10a-hexahydro-6H-1,9-epoxybenzo[c]chromen-4-yl](phenyl)methanone

Date Published: April 01, 2012

Publisher: International Union of Crystallography

Author(s): Gwendoline Cheng Lian Ee, Soek Sin Teh, Huey Chong Kwong, Mohamed Ibrahim Mohamed Tahir, Siau Hui Mah.


The title compound congestiflorone, C28H32O4, which was isolated from the stem bark of Mesua congestiflora, consists of a benzophenone skeleton with two attached pyran rings to which a cyclo­hexane ring and a C6 side chain are bonded. The benzene ring is significantly distorted from planarity (r.m.s. deviation = 0.0007 Å) due to the constraints imposed by junctions with the two pyran rings. The cyclo­hexane ring is in a chair conformation, one pyran ring is in a boat conformation, while the other is a distorted chair. The phenyl and benzene rings make a dihedral angle of 55.85 (9)°. An intra­molecular O—H⋯O hydrogen bond is observed. In the crystal, mol­ecules are linked via C—H⋯O inter­actions.

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For phytochemical investigations of Mesua congestiflora, see: Awang et al. (2010 ▶); Bala & Seshadri (1971 ▶); Ee et al. (2005b ▶); Bandaranayak et al. (1975 ▶); Morel et al. (1999 ▶); Walia & Mukerjee (1984 ▶). For the biological activity of Congestiflora species, see: Pinto et al. (1994 ▶); Ee et al. (2005a ▶); Mazumder et al. (2004 ▶); Verotta et al. (2004 ▶); Huerta-Reyes et al. (2004 ▶). For related structures, see: Hua et al. (2008 ▶); Liu et al. (2005 ▶). For a description of the Cambridge Structural Database, see Allen (2002 ▶)