title: Preparation of five 3-MCPD fatty acid esters, and the effects of their chemical structures on acute oral toxicity in Swiss mice.
abstract: BACKGROUND
  3-monochloro-1, 2-propanediol fatty acid esters (3-MCPDEs) comprise a group of food toxicants formed during food processing. 3-MCPDEs have received increasing attention concerning their potential negative effects on human health. However, reports on the toxicity of 3-MCPD esters are still limited. To determine the effects of fatty acid substitutions on the toxicity of their esters, 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters of 3-MCPD were synthesized and evaluated with respect to their acute oral toxicities in Swiss mice.
  
  
  RESULTS
  3-MCPDEs were obtained through the reaction of 3-MCPD and fatty acid chlorides, and their purities and structures were characterized by ultraperformance liquid chromatography-quadrupole-time of flight-mass spectrometry (UPLC-Q-TOF-MS), infrared,1H and13C spectroscopic analyses. Medial lethal doses of 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters were 2973.8, 2081.4, 2016.3, 5000 and > 5000 mg kg-1body weight. For the first time, 3-MCPDEs were observed for their toxic effects in the thymus and lung. In addition, major histopathological changes, as well as blood urea nitrogen and creatinine, were examined for mice fed the five 3-MCPDEs.
  
  
  CONCLUSIONS
  The results from the present study suggest that the degree of unsaturation, chain length, number of substitution and relative substitution locations of fatty acids might alter the toxicity of 3-MCPDEs. © 2016 Society of Chemical Industry.
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.
authors.forename: Man
authors.initials: M
authors.lastname: Liu
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.|Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Technology & Business University (BTBU), Beijing 100048, China.
authors.forename: Jie
authors.initials: J
authors.lastname: Liu
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.
authors.forename: Yizhen
authors.initials: Y
authors.lastname: Wu
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.|Department of Nutrition and Food Science, University of Maryland, 0112 Skinner Building, College Park, MD 20742, USA.
authors.forename: Boyan
authors.initials: B
authors.lastname: Gao
authors.affiliation: Department of Pathology, School of Medicine, Shanghai Jiao Tong University, Shanghai, 200025, China.
authors.forename: Pingping
authors.initials: P
authors.lastname: Wu
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.
authors.forename: Haiming
authors.initials: H
authors.lastname: Shi
authors.affiliation: Institute of Food and Nutraceutical Science, School of Agriculture & Biology, Shanghai Jiao Tong University, Shanghai, 200240, China.
authors.forename: Xiangjun
authors.initials: X
authors.lastname: Sun
authors.affiliation: Department of Nutrition and Food Science, University of Maryland, 0112 Skinner Building, College Park, MD 20742, USA.|Diet, Genomics, and Immunology Laboratory, Agricultural Research Service (ARS), United States Department of Agriculture (USDA), Beltsville, MD 20705, USA.
authors.forename: Haiqiu
authors.initials: H
authors.lastname: Huang
authors.affiliation: Diet, Genomics, and Immunology Laboratory, Agricultural Research Service (ARS), United States Department of Agriculture (USDA), Beltsville, MD 20705, USA.
authors.forename: Thomas Ty
authors.initials: TT
authors.lastname: Wang
authors.affiliation: Department of Nutrition and Food Science, University of Maryland, 0112 Skinner Building, College Park, MD 20742, USA.
authors.forename: Liangli Lucy
authors.initials: LL
authors.lastname: Yu
mesh_terms: D000818:Animals; D001522:Behavior, Animal / Q000187:drug effects; D001921:Brain / Q000187:drug effects / Q000473:pathology; D004075:Diglycerides / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D005260:Female; D005506:Food Contamination; D005511:Food Handling; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D007928:Lethal Dose 50; D008099:Liver / Q000187:drug effects* / Q000473:pathology; D008297:Male; D051379:Mice; D015394:Molecular Structure; D050178:Monoglycerides / Q000138:chemical synthesis / Q000737:chemistry / Q000633:toxicity*; D009474:Neurons / Q000187:drug effects / Q000473:pathology; D020258:Neurotoxicity Syndromes / Q000097:blood / Q000209:etiology* / Q000473:pathology; D009929:Organ Size / Q000187:drug effects; D011897:Random Allocation; D013329:Structure-Activity Relationship; D013950:Thymus Gland / Q000187:drug effects* / Q000473:pathology; D023382:Toxicity Tests, Acute
chemical_list: D004075:Diglycerides; D006843:Hydrocarbons, Chlorinated; D050178:Monoglycerides
keywords: 3-MCPD fatty acid esters; acute toxicity; structure and toxicity relationships; toxic target organ