Seven isomeric hydrocarbons were detected in the volatile fraction ofthree samples of virgin oliveoil. Chemical ionization mass spectrometry was used to assign themolecular formulas. Theirstructures were confirmed by comparison of retention time and massspectral data with those of asynthetic sample obtained by pentene radical coupling. A finalcharacterization of each chromatographic peak was done by means of a chiral capillary column todistinguish the optically activecompounds from the isomers without chiral centers. For thequantitation the recovery factor inthe oily matrix during the extraction of the volatile fraction wasobtained using a related chemical,the commercially available
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-citronellene. On the basis of theprevious literature and the presentexperiments a tentative rationalization of the involved biochemicalpathway is proposed.Keywords: Virgin olive oil; flavor; lipoxygenase; pentene dimers; radicalcoupling