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

Abstract

The title compound, C 12 H 16 O 4 (systematic name: 2,4-dihydroxy-6-pentylbenzoic acid) is a natural product isolated from C. sanguinea (Schaer.) and is reported to have various pharmacological activities. The molecule is approximately planar (r.m.s. deviation for the non-H atoms = 0.096 Å) and features an intramolecular O—H…O hydrogen bond. In the crystal, each olivetolic acid molecule 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.