In an effort to establish the origin of the fatty acid esters of 3-chloropropanediol, which recently have been isolated in small amounts from goat milk, we compared the molecular species composition of the chlorohydrin diesters and of goat milk triacylglycerols. The chloropropanediol diesters were found to be composed of molecular species containing C10-C18 fatty acids and corresponded closely in carbon number to those calculated for the long chain sn-1,2-diacylglycerol moieties of goat milk triacylglycerols. The molecular species of goat milk total triacylglycerols contained C4-C18 fatty acids. It is suggested that triacylglycerols and chloropropanediol diesters are derived from the same pool of long chain fatty acids. A molecular distillate of bovine milk fat did not contain chloropropanediol diesters, while the available samples of human milk fat were shown to contain alkyldiacylglycerols as the major components of a neutral lipid fraction corresponding in polarity to the chloropropanediol diesters.
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Occurrence and exposure of 3-monochloropropanediol diesters in edible oils and oil-based foodstuffs from the Spanish market.
Food Chem
January 2019
Department of Analytical Chemistry, Nutrition and Food Science, University of Santiago de Compostela, 15782 Santiago de Compostela, Spain; Health Research Institute of Santiago de Compostela (IDIS), University of Santiago de Compostela, 15782 Santiago de Compostela, Spain.
During the industrial refining process of edible oils and the manufacture of oil-based foodstuff, contaminants such as 3-monochloropropanediol (3-MCPD) fatty acid diesters can be produced. One hundred samples of different edible oils and related fatty food purchased from local Spanish markets were analyzed to evaluate the occurrence of these contaminants. Data of seven 3-MCPD diesters together with corresponding total 3-MCPD equivalents are presented.
View Article and Find Full Text PDFThe fatty acid esters of chloropropanediol isolated from goat milk fat in small quantities were subjected to a stereospecific analysis via phospholipase C and phosphocholine esters as intermediates. Synthetic rac-1-chloro-2,3-dioleoyl-propanediol was prepared by standard methods and was used as a control. The stereospecific analyses were performed following a release of the fatty acids from the primary positions of each chloropropanediol diester with pancreatic lipase.
View Article and Find Full Text PDFIn an effort to establish the origin of the fatty acid esters of 3-chloropropanediol, which recently have been isolated in small amounts from goat milk, we compared the molecular species composition of the chlorohydrin diesters and of goat milk triacylglycerols. The chloropropanediol diesters were found to be composed of molecular species containing C10-C18 fatty acids and corresponded closely in carbon number to those calculated for the long chain sn-1,2-diacylglycerol moieties of goat milk triacylglycerols. The molecular species of goat milk total triacylglycerols contained C4-C18 fatty acids.
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