This research was aimed to evaluate the formation mechanism of 3-monochloro-1,2-panediol (3-MCPD) fatty acid esters, a new group of food toxicants detected in many food products, oils and human breast milk. The first part of this study was conducted to test the hypothesis that free radical was formed and mediated the formation of 3-MCPD diesters from diacylglycerol (DAG). For the first time, a radical mechanism was proposed and confirmed. The presence of a cyclic acyloxonium free radical (CAFR) intermediate was first confirmed by quadrupole-time of flight mass spectrometer (Q-TOF-MS) and IR analyses of the reaction mixtures. Furthermore, the possible mechanism involved in the formation of 3-MCPD esters from triacylglycerol (TAG) was investigated. The results indicated that iron ion might catalyze the generation of 3-MCPD esters from TAG. Radicals, generated in the lipid peroxidation, might also be associated with 3-MCPD ester formation. The results of this study might be used to control the level of 3-MCPD esters during oil deodorization.

Formation mechanism of 3-monochloro-1,2-panediol (3-MCPD) fatty acid esters

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.