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R O O + O R1 Cl Cl O O OR 1 R O O
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R OH H
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-H2O OR1
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acylglycerol
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Figure 2.6.13 Proposed mechanism of formation of MCPD-esters from mono- and di-acylglycerols (R = alkyl, R1 = H or COR).
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as a consequence of facile cyclic acyl oxonium ion formation and subsequent ring opening by chloride ion (see Fig. 2.6.13). 2.6.5.3.3 Formation in Malts and Roasted Cereals Studies on the formation of chloropropanols in malts (84) have shown that 3-MCPD can form when malted or unmalted barley is dry roasted (higher than 170 C), and that endogenous lipids and glycerol/acylglycerols in the grain are suf cient to promote this synthesis. The 3-MCPD produced during roasting was correlated with color development, while extended heating at temperatures of 200 C or greater gave a reduction in 3-MCPD, presumably as a result of degradation (84). 2.6.5.4 Mechanisms Involving Enzymes
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The formation of MCPDs has been demonstrated in model systems comprising pepper, oil, and sodium chloride, and over a period of several days (102). As spices are known to be a source of enzyme activity, this was subsequently shown to be a general reaction of a lipase in the presence of chloride and lipid. The highest yield of 3-MCPD was obtained in reaction mixtures containing lipase from Rhizopus oryzae, and all the lipases studied exhibited a high hydrolytic activity toward triglycerides from palm and peanut oil (103). The authors proposed that MCPDs were formed by a lipase-catalyzed reaction between a triacylglycerol and chloride ion. However, it is more likely that MCPDs were formed by the hydrolysis of residual MCPD-esters that are now known to be present in the raw materials used (73). 2.6.5.5 Other Formation Mechanisms of Interest
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In a study of the smoking process, Kuntzer and Weisshaar proposed that 3MCPD generated in smoke from burning wood chips could be derived from
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cellulose (81). A mechanism was proposed for the reaction of chloride ions with acetol (3-hydroxyacetone), a thermal degradation product of cellulose and wood smoke. It is interesting to note that 3-hydroxyacetone is isomeric with the known 3-MCPD intermediate glycidol. 2.6.5.6 Stability and Reactions of MCPDs
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Hamlet et al. studied the degradation reactions of MCPDs in pure water (104) and in bread (96, 105). Under aqueous conditions, 3-MCPD decayed to glycerol, via the intermediate epoxide glycidol, according to rst-order kinetics. The stability of 3-MCPD was sensitive to both pH and temperature, particularly over a range applicable to baked cereal products. In bread dough, the decay of 2-MCPD and 3-MCPD was slower than that in pure water: the decay reaction was inhibited by a decrease in moisture content and the pH drop seen in cooked dough at elevated temperatures. At high temperatures (i.e., >100 C), 2- and 3-MCPD exhibited similar stability. At lower temperatures (i.e., <100 C), this behavior was reversed and 2-MCPD was more stable. It was shown that in bread dough, added 3-MCPD was converted into the isomeric compound 2-MCPD in a mechanism involving the known decay intermediate, glycidol (96, 105). The structure of 3-MCPD indicates that the compound should undergo reactions characteristic of both alcohols and alkyl chlorides. For example, 3MCPD is known to react readily with alcohols, aldehydes, amino compounds, ammonia, ketones, organic acids, and thiols (106). Some of these reaction products, such as 3-MCPD-derived amino alcohols, dihydroxypropylamines, and amino acids, have been identi ed in HVPs (106 108). Model system studies (107, 108) have shown that the reaction of 3-MCPD with either ammonia or amino acids occurs readily and at moderate temperatures (20 90 C). The reactions of cysteine and glutathione with 3-MCPD have also been reported (109).
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MITIGATION
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Manufacturers of HVPs and soy sauces and producers of wet-strength resins for food contact applications have made considerable efforts to reduce chloropropanols in, and contamination of foods from, their products. For example, in alkaline media both 2- and 3-MCPD are decomposed to glycerol (110, 111) and hence alkalization is a method that is used commercially to reduce the level of MCPDs in protein hydrolysates (112) and also in wet-strength resins (113). However, strategies to reduce chloropropanols and chloroesters in other products have not yet been fully explored and may not be possible for all foodstuffs. These strategies need to consider whether interventions to reduce the risk of chloropropanols and chloroesters might increase the risk of other process contaminants, such as furan or acrylamide (114). For example,
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