Formation of multiple-membered heterocycles in monochloropropanediol esters using diacylglycerol and glutamic or aminoadipic acids.

Monochloropropanol esters (MCPDE) might pose a risk to human health are often present in thermally processed foods. The effect of 20 amino acids on the formation of MCPDE was examined in a palm oil model reaction. The findings indicated that glutamic and aminoadipic acids markedly enhance formation of MCPDE. Diacylglycerol was the primary precursor for MCPDE formation. Glutamic and aminoadipic acids could form five- or six-membered heterocycle compounds with diacylglycerol. The structures of these intermediates were identified using FT-IR spectra and LC-MS/MS. It is proposed that glutamic or aminoadipic acids reacts with glycerol diesters to form intermediates that promote formation of MCPDE. Our results provide a theoretical basis for the formation of MCPDE in thermal processing, which implies formation can be reduced by preventing contact between glutamate and glycerol esters.