酸化脂質による褐変の初期反応機構について (水産加工品の褐変に関する研究-4,5-)

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To clarify the mechanism of the browning reaction observed in fish products, the separation and identification of a few intermediate products were carried out in model browning systems. Acetaldehyde and 2-hexenal, the main aldehydes in autoxidized oil, were incubated with ammonia ethanol solution at 37°C for 4 days. From the reaction mixture containing acetaldehyde, carbonyl compounds were separated as their 2, 4-dinitrophenylhydrazones by T. L. C. (Fig. 2). As a result, crotonaldehyde and aldol were identified as the main products (Table 1), and the occur-rence of these aldehydes indicated that aldol condensation had occurred. As crotonaldehyde has a higher browning potential than acetaldehyde (Fig. 3), it is assumed to be polymerized without much accumulation. From 2-hexenal, the formation of 2-(1-butenyl)-octa-2, 4-dienal as the first browning substance was proved by elementary analysis (Table 2), NMR spectrum (Fig. 5) and mass spectrum (Fig. 5). This substance was formed also by aldol condensation and the dehydration of two molecules of 2-hexenal. Correlating these results with the facts that the browning of acetaldehyde was faster in DMSO than in ethanol (Fig. 4), and the selective reduction of carbonyl groups faded the browning substances almost completely (Fig. 7), the authors concluded that aldol condensation was the main reaction in the early stage of browning.
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