Squalene oxidation products: Monitoring the formation, characterisation and pro-oxidant activity

Squalene (SQ), a precursor of sterols and terpenoids is a functional lipid of high importance in the food and pharmaceutical sectors. SQ oxidation studies are rather limited compared with those for other olefins. The aim of the present study was to monitor the formation of SQ oxidation products under different conditions (temperature, air supply), to characterise the most abundant of them by spectroscopic techniques and then examine their pro-oxidant activity in a model lipid substrate. Squalane (SQA), the saturated analogue of SQ, was used as a reference compound. FT-MIR analysis indicated the presence of alcohols, epoxides, aldehydes, and ketones. GC-MS was used to characterise SQ primary oxidation and scission products. The presence of epoxides was further confirmed by means of H-1 NMR and C-13 NMR spectroscopy. It could be argued that SQ stability is due to its stereochemistry and specifically to the presence of methyl groups next to the double bonds. The pro-oxidant activity of SQ oxidation products was evident at 62 and 40 degrees C and suppressed only in the presence of primary antioxidants, not of SQ. The present work adds to the characterisation of SQ oxidised products. To our knowledge their pro-oxidant activity has never been examined before.