title: Reactions of aqueous chlorine and chlorine dioxide with model food compounds.
abstract: Chlorine and chlorine dioxide (ClO2), common disinfecting and bleaching chemicals used in the food industry, are potent oxidizing and chlorinating agents. Unfortunately, little is known about the nature of the reactions of chlorine with organic food constituents. This presentation reviews published information concerning the reactions of chlorine gas (Cl2[g]), aqueous chlorine, and ClO2 with model food compounds, the fate of chlorine during the chlorination of specific food products, and the potential toxicity of the reaction products. Fatty acids and their methyl esters react with chlorine with the degree of incorporation corresponding to their degree of unsaturation. Aqueous chlorine oxidizes and chlorinates lipids and amino acids much more readily than ClO2. Several amino acids are highly susceptible to oxidation and chlorination by chlorine compounds. Reactions of chlorine and ClO2 with several food products, including flour and shrimp, have also been characterized. In one model system, 99% of Cl2(g) either reacted with components of flour or was consumed by oxidation/chlorination reactions. The lipids extracted from the chlorinated flour contained significant amounts of chlorine. Exposure of shrimp to hypochlorous acid (HOCl) solution resulted in significant incorporation of chlorine into the edible portion. Although significant quantities of chlorine can be incorporated into specific model compounds and food products, the health risks associated with exposure to chlorinated organic products are unknown. Preliminary studies using the Ames Salmonella/microsome mutagenicity assay indicate that the reaction products from mixtures of aqueous chlorine and various lipids or tryptophan are nonmutagenic. Nevertheless, additional studies are warranted, so that the toxicological significance of these reaction products can be understood more fully.
mesh_terms: D000596:Amino Acids; D002241:Carbohydrates; D055598:Chemical Phenomena; D002621:Chemistry; D002713:Chlorine / Q000009:adverse effects*; D017606:Chlorine Compounds; D004202:Disinfectants / Q000009:adverse effects*; D005502:Food; D005511:Food Handling; D008055:Lipids; D010087:Oxides / Q000009:adverse effects*; D010455:Peptides; D011506:Proteins; D014867:Water
chemical_list: D000596:Amino Acids; D002241:Carbohydrates; D017606:Chlorine Compounds; D004202:Disinfectants; D008055:Lipids; D010087:Oxides; D010455:Peptides; D011506:Proteins; D014867:Water; D002713:Chlorine; C025109:chlorine dioxide