Preparation of five 3‐MCPD fatty acid esters, and the effects of their chemical structures on acute oral toxicity in Swiss mice

• Published in: Journal of the science of food and agriculture 2017-02, Vol.97 (3), p.841-848
• Main Authors: Liu, Man, Liu, Jie, Wu, Yizhen, Gao, Boyan, Wu, Pingping, Shi, Haiming, Sun, Xiangjun, Huang, Haiqiu, Wang, Thomas TY, Yu, Liangli(Lucy)
• Format: Article
• Language: English
• Subjects: 3‐MCPD fatty acid esters; acute toxicity; Animals; Behavior, Animal - drug effects; Brain - drug effects; Brain - pathology; Chains; Chlorides; Diglycerides - chemical synthesis; Diglycerides - chemistry; Diglycerides - toxicity; Esters; Fatty acids; Female; Food Contamination; Food contamination & poisoning; Food Handling; Food safety; Foods; Hydrocarbons, Chlorinated - chemical synthesis; Hydrocarbons, Chlorinated - chemistry; Hydrocarbons, Chlorinated - toxicity; Lethal Dose 50; Liquids; Liver - drug effects; Liver - pathology; Male; Mice; Molecular Structure; Monoglycerides - chemical synthesis; Monoglycerides - chemistry; Monoglycerides - toxicity; Neurons - drug effects; Neurons - pathology; Neurotoxicity Syndromes - blood; Neurotoxicity Syndromes - etiology; Neurotoxicity Syndromes - pathology; Organ Size - drug effects; Random Allocation; structure and toxicity relationships; Structure-Activity Relationship; Thymus Gland - drug effects; Thymus Gland - pathology; toxic target organ; Toxicity; Toxicity Tests, Acute
• ISSN: 0022-5142; 1097-0010
• DOI: 10.1002/jsfa.7805

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 and 13C 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−1 body 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. CONCLUSION 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