cis/trans-Isomerisation of triolein, trilinolein and trilinolenin induced by heat treatment

To estimate the trans-fatty acid production of edible oils during the frying process, 1.0 g of triolein, trilinolein and trilinolenin, as representative oils, were heated at 180 °C for a defined period. The amounts of trans-fatty acids in heated triacylglycerols were quantitatively determined by gas chromatography after methylation. It was revealed that heating induced cis to trans-isomerisation of unsaturated triacylglycerols, and that trans-fatty acid amounts increased gradually, depending on the heating period. For example, trans-isomer amounts in triolein, trilinolein and trilinolenin (per gram) were 5.8 mg, 3.1 mg and 6.5 mg, respectively, after 8 h incubation at 180 °C. At that time, the contents of polar compounds contained in the heated triolein, trilinolein and trilinolenin were 22%, 27% and 31%, respectively. When triolein was heated under a N2 stream, neither trans-isomerisation nor polar compounds were detected. The addition of α-tocopherol (1.0%) to triolein significantly prevented not only lipid oxidation but also trans-isomerisation during heating. A commercially available vegetable oil was also heated under the same conditions as these model oils. Compared with the trans-isomerisation in model oils, the degree of trans-isomerisation in the edible oil was relatively low. Tocopherols in the oil would prevent not only lipid oxidation but also isomerisation. These results suggest that the geometric isomerisation of unsaturated fatty acids during heating accompanies lipid oxidation.