title: Formation of 3-MCPD Fatty Acid Esters from Monostearoyl Glycerol and the Thermal Stability of 3-MCPD Monoesters.
abstract: Formation of 3-monochloropropanediol (3-MCPD) esters from monostearoyl glycerol (MSG) was investigated under high temperature and low moisture conditions. Different organic and inorganic chlorides, including lindane, KCl, CaCl2, NaCl, MgCl2, AlCl3, CuCl2, MnCl2, SnCl2, ZnCl2, and FeCl3, were evaluated for their potential to react with MSG to form 3-MCPD and glycidyl esters at 120 and 240 °C using a UPLC-Q-TOF MS analysis. The results indicated that different chlorine compounds differed in their capacity to react with MSG and formed different products including 3-MCPD mono- and diesters, distearoylglycerol, and glycidyl esters. According to electron spin resonance (ESR) and Fourier transform infrared (FT-IR) spectroscopies, free radical mediated formation mechanisms involving either five-membered or six-membered cyclic acyloxonium free radicals (CAFR) from monoacylglycerol (MAG) were proposed. Tandem quadrupole-time-of-flight (Q-TOF) MS and MS/MS analyses confirmed the free radical mechanisms. In addition, the results from the present study showed that 3-MCPD monoester could be degraded upon thermal treatment and suggested a possible catalytic role of Fe3+under the experimental conditions.
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.
authors: Yue
authors: Y
authors: Zhao
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.
authors: Yaqiong
authors: Y
authors: Zhang
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.
authors: Zhongfei
authors: Z
authors: Zhang
authors: Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology & Business University (BTBU) , Beijing 100048, China.
authors: Jie
authors: J
authors: Liu
authors: Yi-Lin
authors: YL
authors: Wang
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.|Department of Nutrition and Food Science, University of Maryland , College Park, Maryland 20742, United States.
authors: Boyan
authors: B
authors: Gao
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.
authors: Yuge
authors: Y
authors: Niu
authors: Institute of Food and Nutraceutical Science, School of Agriculture and Biology, Shanghai Jiao Tong University , Shanghai 200240, China.
authors: Xiangjun
authors: X
authors: Sun
authors: Department of Nutrition and Food Science, University of Maryland , College Park, Maryland 20742, United States.
authors: Liangli
authors: L
authors: Yu
mesh_terms: D004578:Electron Spin Resonance Spectroscopy; D004952:Esters / Q000737:chemistry*; D005227:Fatty Acids / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D005990:Glycerol / Q000737:chemistry*; D006358:Hot Temperature; D017550:Spectroscopy, Fourier Transform Infrared; D053719:Tandem Mass Spectrometry; D000517:alpha-Chlorohydrin / Q000737:chemistry*
chemical_list: D004952:Esters; D005227:Fatty Acids; D005609:Free Radicals; D000517:alpha-Chlorohydrin; D005990:Glycerol
keywords: 3-MCPD esters; Fe3+; free radical mechanism; lipid chemistry; thermal stability