Cannabidiol revisited

Abstract

The crystal structure of cannabidiol, C 21 H 30 O 2 , {systematic name: 2-[(1 R ,6 R )-3-methyl-6-(prop-1-en-2-yl)cyclohex-2-enyl]-5-pentylbenzene-1,3-diol}, was determined earlier by Jones et al. [(1977). Acta Cryst. B 33 , 3211–3214] and Ottersen & Rosenqvist [(1977). Acta Chem. Scand. B31 , 749–755]. In both investigations, the absolute configuration is given as R , R , referring to Mechoulam et al. [(1967. J. Am. Chem. Soc. 89 , 4552–4554]. In the latter, the absolute configuration was identified by chemical means. Using the advantages of modern single-crystal X-ray diffractometers such as area detectors and high-intensity radiation sources, a high-quality structure determination including the absolute configuration was possible and is shown in this work. Furthermore, the rather uncommon Cu K β wavelength radiation was applied for the structure determination, which confirmed the absolute structure to be R,R .