Identification of alpha-tocopherol oxidation products in triolein at elevated temperatures

The effect of high-temperature treatment on the stability of alpha-tocopherol (1) in triolein was assessed under a reduced-pressure atmosphere (4-40 mbar) simulating the deodorization step of the refining of vegetable oils. A marked degradation of 1 was observed, which increased with increasing temperature (180-260 degrees C) and heating time (20-80 min). The degradation of 1 in triolein at 240 degrees C was inhibited by the addition of the synthetic antioxidant TBHQ or when heating was performed under nitrogen atmosphere, indicating oxidative degradation. The oxidation products were isolated and identified as alpha-tocopherolquinone (2), 4a,5-epoxy-alpha-tocopherolquinone (3), and 7,8-epoxy-alpha-tocopherolquinone (4).