Sesquiterpene, alkene, and alkane hydrocarbons in virgin olive oils of different varieties and geographical origins

Abstract

The hydrocarbon fraction of 30 virgin olive oils was analyzed, focusing in particular on the sesquiterpenes. The oil samples were of different geographical origins and obtained from different olive varieties. The hydrocarbon fraction was isolated by silica gel column chromatography of the unsaponifiable fraction of the oils. The sesquiterpene hydrocarbons were then fractionated, on the basis of their degree of unsaturation, by AgNO3 TLC and silica gel AgNO3 column chromatography. The composition of the sesquiterpenes was more complex than previously reported. Among the 31 sesquiterpenes detected, 24 have been tentatively identified, by comparison of the linear retention indices on two capillary columns of different polarities and mass spectra with those reported in the literature. The total concentration of the sesquiterpenes in the oils analyzed ranged from about 2 to 37 ppm. Among the sesquiterpenes the more abundant were alpha-farnesene, alpha-copaene, eremophyllene, and alpha-muurolene. The alkenes present in the hydrocarbon fraction were isolated by TLC AgNO3 and characterized by GC-MS of their dimethyl disulfide derivatives. The series of n-Delta9-alkenes from C22 to C27, 8-heptadecene, and 6,10-dimethyl-1-undecene were detected. Among the n-alkanes, those with an odd number of carbon atoms predominated in all of the analyzed oils, the most common being C23, C25, C27, and C29. The concentration of the n-alkenes ranged from about 0.5 to 2 ppm, whereas for the n-alkanes the range was from 30 to 177 ppm.