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...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2007-04, Vol.55 (8), p.3037-3043
Main Authors: Coleman, William Monroe, Dube, Michael Frances, Ashraf-Khorassani, Mehdi, Taylor, Larry Thomas
Format: Article
Language:English
Subjects:
Artemisia - chemistry
Artemisia pallens
Biological and medical sciences
carbon dioxide
Chromatography, Gas
Chromatography, Supercritical Fluid
davanone
essential oils
extraction
Fat industries
Food industries
Fundamental and applied biological sciences. Psychology
Gas Chromatography-Mass Spectrometry
Isomerism
isomers
Magnetic Resonance Spectroscopy
Plant Oils - chemistry
Sesquiterpenes - chemistry
sesquiterpenoids
Smell
Stereoisomerism
supercritical fluid extraction
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Summary: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
ISSN:0021-8561
1520-5118
DOI:10.1021/jf062652y