Add time:08/09/2019         Source:sciencedirect.com

Dinitrogen trioxide (N2O3) was reacted with methyl oleate and the residual N2O3 removed. The resulting products were capable of nitrosating 2,6-dimethylmorpholine above 80°C with a maximum yield of nitrosamine at 130°C. N-nitroso-2,6-dimethylmorpholine formation was first order in nitrosating agent. When the reaction products were added to ground uncured pork and fried, N-nitrosodimethylamine and N-nitrosopyrrolidine were formed in amounts similar to those formed in fried bacon. 2,3-Dimethyl-2-nitro-3-nitrosobutane also nitrosated amines in the presence of pork lipids. Individual products were separated by HPLC and identified by IR and MS as nitronitroso-, dinitro-, nitronitrate-, and nitro oxime additions to methyl oleate. The nitronitroso derivative, as previously predicted, occurred in the fraction with the greatest capacity to nitrosate the amine. The products of the reaction between oleic acid and N2O3 were mutagenic in Salmonella typhimurium strain TA1535 without S-9 activation showing a 5·5- to 66-fold increase in revertants at doses of 90 to 200 μg/plate. These findings support, but do not prove, the theory that nitrite reacts with unsaturated lipids in bacon to form compounds which are responsible for nitrosamine formation during frying.

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