Antioxidant activity evaluation of alkyl hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives

The antioxidant activity of a new series of alkyl hydroxytyrosyl ethers was evaluated by the Rancimat test in a lipophilic food matrix and by the FRAP, ABTS and DPPH assays in a hydrophilic medium, and compared to free hydroxytyrosol (HTy), butylhydroxytoluene (BHT) and α-tocopherol. All methods used to assess the antioxidant activity of the new compounds emphasised the importance of the ortho-diphenolic structure on the maintenance of the high antioxidant activity associated with free HTy. The results obtained support the ‘polar paradox’ since the antioxidant activity of the lipophilic hydroxytyrosyl ethers was slightly lower in bulk oils and higher in hydrophilic media in comparison with their reference HTy. Although the length of the alkyl chain did not significantly affect the antioxidant activity in bulk oils, it did have a positive influence in hydrophilic medium for ethers with a short alkyl chain (methyl, ethyl and propyl), while ethers with longer alkyl chain (butyl, hexyl, octyl, dodecyl and octadecyl) maintained or even decreased their antioxidant activity, probably due to the steric effect of the side chains. In conclusion, these results show the strong antioxidant activity of a new group of lipophilic HTy derivatives that satisfies the food industry demands for new antioxidants with potential use as functional ingredients to improve the quality and nutritional properties of foods.