Formation of Oleic Acid Chlorohydrins in Vegetables during Postharvest Chlorine Disinfection

• Published in: Environmental science & technology Vol. 56; no. 2; pp. 1233 - 1243
• Main Authors: Simpson, Adam M.-A, Suh, Min-Jeong, Plewa, Michael J, Mitch, William A
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 18.01.2022
• Subjects: Animals; Biopolymers; Brassica; Broccoli; Carrots; Chlorine; Chlorohydrins; CHO Cells; Cricetinae; Cricetulus; Cytotoxicity; Disinfectants; Disinfection; Drinking water; Fatty acids; Foodborne pathogens; Haloacetic acids; Isomers; Leaves; Lipids; Micelles; Oleic Acid; Shredding; Spinach; Toxicity; Treatment and Resource Recovery; Trihalomethanes; Vegetables; Yield; postharvest washing; fatty acid; chlorohydrin; chlorine
• ISSN: 0013-936X; 1520-5851
• DOI: 10.1021/acs.est.1c04362

High chlorine doses (50–200 mg/L) are used in postharvest washing facilities to control foodborne pathogen outbreaks. However, chlorine can react with biopolymers (e.g., lipids) within the produce to form chlorinated byproducts that remain in the food. During chlorination of micelles of oleic acid, an 18-carbon alkene fatty acid, chlorine added rapidly across the double bond to form the two 9,10-chlorohydrin isomers at a 100% yield. The molar conversion of lipid-bound oleic acid to 9,10-chlorohydrins in chlorine-treated glyceryl trioleate and produce was much lower, reflecting the restricted access of chlorine to lipids. Yields from spinach treated with 100 mg/L chlorine at 7.5 °C for 2 min increased from 0.05% (0.9 nmol/g-spinach) for whole leaf spinach to 0.11% (2 nmol/g) when shredding increased chlorine access. Increasing temperature (21 °C) and chlorine contact time (15 min) increased yields from shredded spinach to 0.83% (22 nmol/g) at 100 mg/L chlorine and to 1.8% (53 nmol/g) for 200 mg/L chlorine. Oleic acid 9,10-chlorohydrin concentrations were 2.4–2.7 nmol/g for chlorine-treated (100 mg/L chlorine at 7.5 °C for 2 min) broccoli, carrots, and butterhead lettuce, but 0.5–1 nmol/g for cabbage, kale, and red leaf lettuce. Protein-bound chlorotyrosine formation was higher in the same vegetables (5–32 nmol/g). The Chinese hamster ovary cell chronic cytotoxicity LC50 value for oleic acid 9,10-chlorohydrins was 0.106 mM. The cytotoxicity associated with the chlorohydrins and chlorotyrosines in low masses (9–52 g) of chlorine-washed vegetables would be comparable to that associated with trihalomethanes and haloacetic acids at levels of regulatory concern in drinking water.