Crystal structure of olivetolic acid: a natural product from Cetrelia sanguinea (Schaer.)

Friardi Ismed; Aulia Farhan; Amri Bakhtiar; Erizal Zaini; Yuda Prasetya Nugraha; Okky Dwichandra Putra; Hidehiro Uekusa

doi:10.1107/S2056989016016273

Crystal structure of olivetolic acid: a natural product from Cetrelia sanguinea (Schaer.)

Acta Crystallogr E Crystallogr Commun. 2016 Oct 18;72(Pt 11):1587-1589. doi: 10.1107/S2056989016016273. eCollection 2016 Nov 1.

Authors

Friardi Ismed¹, Aulia Farhan¹, Amri Bakhtiar¹, Erizal Zaini¹, Yuda Prasetya Nugraha², Okky Dwichandra Putra², Hidehiro Uekusa²

Affiliations

¹ The Laboratory of Natural Resource of Sumatra (LBS) and Faculty of Pharmacy, Andalas University, 26163 Padang, Indonesia.
² Department of Chemistry and Materials Science, Tokyo Institute of Technology, Ookayama 2-12-1, Meguro-ku, Tokyo 152-8551, Japan.

Abstract

The title compound, C₁₂H₁₆O₄ (systematic name: 2,4-dihy-droxy-6-pentyl-benzoic acid) is a natural product isolated from C. sanguinea (Schaer.) and is reported to have various pharmacological activities. The mol-ecule is approximately planar (r.m.s. deviation for the non-H atoms = 0.096 Å) and features an intra-molecular O-H⋯O hydrogen bond. In the crystal, each olivetolic acid mol-ecule is connected to three neighbours via O-H⋯O hydrogen bonds, generating (10-1) sheets. This crystal is essentially isostructural with a related resorcinolic acid with a longer alkyl chain.

Keywords: Cetrelia sanguinea; crystal structure; olivetolic acid.