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

Author
item LIU, MAN - Shanghai Jiaotong University
item LIU, JIE - Shanghai Jiaotong University
item WU, YIZEN - Shanghai Jiaotong University
item GAO, BOYAN - Shanghai Jiaotong University
item WU, PINGPING - Shanghai Jiaotong University
item SHI, HAIMING - Shanghai Jiaotong University
item SUN, XIANGJUN - Shanghai Jiaotong University
item HUANG, HAIQUI - University Of Maryland
item Wang, Thomas - Tom
item YU, LIANGLI - University Of Maryland

Submitted to: Journal of Food Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 5/17/2016
Publication Date: 5/17/2016
Citation: Liu, M., Liu, J., Wu, Y., Gao, B., Wu, P., Shi, H., Sun, X., Huang, H., Wang, T.T., Yu, L. 2016. Preparation of five 3-MCPD fatty acid esters and the effects of their chemical structures on acute oral toxicity in Swiss mice. Journal of Food Chemistry. doi: 10.1002/jsfa.7805.

Interpretive Summary: Fatty acid esters of 3-monochloro-1, 2-propanediol (3-MCPDEs) are emerging food contaminants and have raised significant food safety concern. The structure and efficacy relationship of MCPDEs remains unclear. The present study aimed to investigate the potential influence of fatty acid chain length, unsaturation degree, number of fatty acids, and relative fatty acid locations on overall oral acute toxicity of 3-MCPDEs. Fatty acid esters of 3-monochloro-1, 2-propanediol (3-MCPDEs), including 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters were synthetized and examined for their acute oral toxicities in Swiss mice. 3-MCPDEs were obtained through the reaction of 3-MCPD and fatty acid chlorides and their purities and structures were characterized by UPLC-TOF-MS, IR, 1H and 13C spectroscopic analyses. Medial lethal doses (LD50) 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 greater than 5000 mg/kg body weight (BW), respectively. For the first time, 3-MCPDEs were observed for their toxic effects in brain, thymus, and lung. In addition, major histopathological changes and blood urea nitrogen and creatinine were examined for the five 3-MCPDEs. The results from this study suggested that the degree of unsaturation, chain length, number of substitution, and relative substitution locations of fatty acids might alter the toxicity of the corresponding 3-MCPDEs. The findings may advance our understanding of 3-MCPDEs toxicity and provide science-based information for food safety scientist interested in structure-efficacy relation of contaminants from food.

Technical Abstract: Fatty acid esters of 3-monochloro-1, 2-propanediol (3-MCPDEs), including 1-stearic, 1-oleic, 1-linoleic, 1-linoleic-2-palmitic and 1-palmitic-2-linoleic acid esters, were synthetized and examined for their acute oral toxicities in Swiss mice. 3-MCPDEs were obtained through the reaction of 3-MCPD and fatty acid chlorides, and their purities and structures were characterized by UPLC-TOF-MS, IR, 1H and 13C spectroscopic analyses. Medial lethal doses (LD50) 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 greater than 5000 mg/kg body weight (BW), respectively. For the first time, 3-MCPDEs were observed for their toxic effects in brain, thymus, and lung. In addition, major histopathological changes and blood urea nitrogen and creatinine were examined for the five 3-MCPDEs. The results from this study suggested that the degree of unsaturation, chain length, number of substitution, and relative substitution locations of fatty acids might alter the toxicity of the corresponding 3-MCPDEs. The findings may advance our understanding of 3-MCPDEs toxicity and may improve food safety.