The influence of the unsaturation degree of different triacylglycerols (tristearin, triolein, trilinolein and trilinolenin) on cholesterol oxidation at 180 °C, was evaluated. Cholesterol degraded faster when heated alone than in the presence of triacylglycerols; moreover, the more unsaturated the matrix, the slower the degradation of cholesterol. Both cholesterol and triacylglycerols degradation fit a first order kinetic model (R(2)>0.9), except for the tristearin sample. Cholesterol oxidation products (COPs) and peroxides were formed during the heating treatment. The presence of any type of lipid matrix postponed and decreased the maximum concentration of both oxidation parameters. Maximum total COPs concentrations were achieved at 20 min in neat cholesterol, 120 min in tristearin and triolein and 180 min in polyunsaturated matrix samples. 7-Ketocholesterol was the main COP in most cases during the whole heating treatment. Both the presence of triacylglycerols and their unsaturation degree inhibited cholesterol thermooxidation at 180 °C.