4.7 Article

Trans-Hydroxy, Trans-Epoxy, and Erythro-dihydroxy Fatty Acids Increase during Deep-Frying

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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 71, 期 19, 页码 7508-7513

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AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.3c00964

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autoxidation; heat; liquid chromatography-mass spectrometry; oxylipins; sunflower oil

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New parameters related to the condition of frying oils were discovered by studying the oxidation products of fatty acids during deep-frying.
Deep-frying of food is a common cooking technique causing thermal oxidation of fatty acids (FA). Here, we investigated for the first time the formation of hydroxy-, epoxy-and dihydroxy-FA derived from oleic, linoleic (LA), and alpha-linolenic acid (ALA) during frying. Potato chips were fried in high-oleic sunflower oil for 4 x 5 cycles on 2 days, and the oil was comprehensively analyzed by liquid chromatography-tandem mass spectrometry. During frying, the E,Z-9-and E,Z-13-hydroperoxy-LA and-ALA concentrations decrease while their corresponding hydroxy-FA remain constant. The concentrations of both E,E-9-/ 13-hydroperoxy-LA and E,E-9-/13-hydroxy-LA increase with the frying cycles, which is also found for the concentration of trans epoxy-FA. The increase in trans-epoxy-FA is more pronounced than that of the corresponding cis-epoxy-FA, exceeding their concentrations on the second day of frying. This selective change in the cis-/trans-epoxy-FA ratio is also observed for their hydrolysis products: concentrations of erythro-dihydroxy-FA, derived from trans-epoxy-FA, increase during frying stronger than threo- dihydroxy-FA derived from cis-epoxy-FA. Based on these data, we suggest that the ratio of E,E-/E,Z-hydroxy-FA, in combination with the cis-/trans-epoxy-FA ratio, as well as the threo-/erythro-dihydroxy-FA ratio are promising new parameters to evaluate the heating of edible oils and to characterize the status of frying oils.

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