Synthesis of 2-Monochloropanol Fatty Acid Esters and Their Acute Oral Toxicities in Swiss Mice.
Zhongfei ZhangPuyu YangBoyan GaoGuoren HuangMan LiuLiangli Lucy YuPublished in: Journal of agricultural and food chemistry (2019)
A novel synthetic route was designed, developed, and utilized to synthesize six high-purity 2-monochloropropanediol fatty acid esters (2-MCPD esters), a group of potential processing-induced food contaminants. A chlorine atom was introduced to C-2 of a diethyl malonate molecule, which was reduced by NaBH4 and followed by esterification using fatty acids. The reaction products were isolated and purified using silica gel columns to obtain three 2-MCPD monoesters and three diesters at about 50-54% and 56-59% yields, respectively. In addition, 2-MCPD monopalmitate and dipalmitate were examined for their acute oral toxicities in Swiss mice. The LD50 values of 2-MCPD mono- and dipalmitate were greater than 5000 mg/kg body weight (BW), along with detectable nephrotoxicity and testicular toxicity. The results of this study may promote future investigation of MCPD ester toxicology and detection.
Keyphrases
- fatty acid
- body weight
- drug induced
- liver failure
- respiratory failure
- drinking water
- high fat diet induced
- aortic dissection
- human health
- high glucose
- molecular dynamics
- mass spectrometry
- hepatitis b virus
- current status
- intensive care unit
- wild type
- risk assessment
- metabolic syndrome
- endothelial cells
- electron transfer
- sensitive detection