Identification of 9(E),11(E)-18:2 fatty acid methyl ester at trace level in thermal stressed olive oils by GC coupled to acetonitrile CI-MS and CI-MS/MS, a possible marker for adulteration by addition of deodorized olive oil

The olive oil market is suffering from sophisticated illegal treatments. One common adulteration process consists of the addition to virgin olive oil of lower quality oils, such as "lampante" oil, an inexpensive oil and with some organoleptic defects, which is then submitted to thermal deodorization under vacuum processes for removal of the undesired flavor components. Such a blending may not have a huge influence on the chemical composition and may not significantly affect the parameters usually checked as quality indicators, although the organoleptic properties may change. As a consequence, a major effort is being devoted to find reliable markers able to unmask such adulterations. We report here the complete characterization of a compound, detected at trace levels exclusively in thermal stressed oils, which could be a candidate marker for adulteration. The investigation, carried out by GC-MS and GC-MS/MS, provided its complete structure, including the stereochemistry, shown to be a 9(E),11(E)-18:2 fatty acid methyl ester. Experimental data also confirmed the influence of both temperature and heating time on formation and concentration of this compound.