Isomeric Enhancement of Davanone from Natural Davana Oil Aided by Supercritical Carbon Dioxide

The chemical nature of davanone isolated from natural davana oil via packed column preparative supercritical fluid chromatography with a carbon dioxide-based mobile phase has been defined. Analyses used to characterize davanone included nuclear magnetic resonance spectroscopy, optical rotation, mass spectrometry, headspace solid-phase microextraction, enantiomeric purity via gas chromatography (GC), and GC-coupled olfactometry. For comparison, natural davana oil was subjected to the same types of measurements. The enriched davanone sample was nearly 100% optically pure. This indicates that fractionation of the davana oil with supercritical fluids at near room temperature had little effect on the optical integrity of the sample. Keywords: Chiral chromatography; davana oil; davanone; olfactometry; supercritical fluid extraction