Novel phenolic antioxidants: 2a (6 0 -hydroxy-2 0 , 5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3-methoxy-4-hydroxycinnamate, 2b (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3,5-dimethoxy-4-hydroxycinnamate, 2c (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -yl)methyl 3,4-dihydroxycinnamate, and 3 (6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)methyl (6 0 -hydroxy-2 0 ,5 0 ,7 0 ,8 0 -tetramethylchroman-2 0 -carboxylate) have been prepared in good yields and fully characterized by 1 H and 13 C NMR, and HRMS. Their radical scavenging activities have been evaluated by DPPH and ORAC assays. Each of the synthesized antioxidants exhibited significantly higher radical scavenging activities than trolox and a-tocopherol. These novel antioxidants efficiently protected canola oil triacylglycerides (CTG) during accelerated storage and frying. Compounds 2c and 3 were significantly more efficient than a-tocopherol protecting CTG under accelerated storage. All new antioxidants were more efficient than a-tocopherol under frying conditions and present significantly higher thermal stability.