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Published on: December 27, 2018
Kinetics of Squalene Quenching Singlet Oxygen and the Thermal Degradation Products Identification
Yunping Yao1, Yue Zheng1, Haiting Dai1
1State Key Laboratory of Food Nutrition and Safety, Key Laboratory of Food Quality and Health of Tianjin, Tianjin University of Science & Technology, 300457 Tianjin, China.
Abstract:
Squalene has been proven to possess various bioactive functions that are widely present in vegetable oils. A more comprehensive understanding of the reaction behavior of squalene under oxidative conditions was achieved by studying its antioxidant capacity and thermal degradation products. The total singlet oxygen quenching rate constant (kr + kq) of squalene was 3.8 × 107 M-1 s-1, and both physical and chemical quenching mechanisms equally contribute to the overall singlet oxygen quenching. Fourteen degradation products of squalene were identified at 180 °C by using gas chromatography-mass spectrometry (GC-MS). Combining with DFT calculations, the thermal degradation pathway of squalene was proposed: the aldehydes, ketones, and alcohols, and epoxy compounds were formed by the homolytic cleavage of squalene hydroperoxides to form alkoxy radicals, followed by β-scission of the alkoxyl radicals at adjacent C-C bonds or intramolecular cyclization.
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