Nitrosation of methyl N-methylanthranilate

The nitrosation of methyl N-methylanthranilate (MMA), which is permitted to be used to foods as flavor in Japan, with equimolar nitrite was measured at 37°C at the concentrations of 10-1-10mM of both reactants. MMA was nitrosated very easily, and when 0.1mM of MMA was reacted with equimolar sodium nitrite at pH 2.0 fbr 5min and at pH 3.0 for 20min, the yields of methyl N-methyl-N-nitrosoanthranilate (NO-MMA) were 89.5% and 82.6%, respectively. The rate of nitrosation was found to be dependent on the acidity of reaction mixture and the highest yields of NO-MMA was obtained below pH 2.0 at the MMA concentration of 0.2mM for 5min. A mutation test of NO-MMA was carried out, but NO-MMA was non-mutagenic to Salmonella typhimurium tester strain TA 100 and TA 98 in the presence and absence of the metabolic activation system (S9 mix).