Formation of mutagens by sorbic acid-nitrite reaction: effects of reaction conditions on biological activities

Mutagen Formation in the Reaction of Nitrite with the Food Components Analogous to Sorbic Acid

“…However, no mutagenicity was detected by the Ames test using S. typhimurium TA 100 and TA 98 strains with or without S-9 mix. The muta- genicity of ethylnitrolic acid has already been reported 4 ) and it showed the same mutagenic profile as No. 2 (5) (positive in the rec-assay but negative in the Ames test).…”

“…2 (5) and ethylnitrolic acid (7) showed strong mutagenicity in the rec-assay Downloaded by [University of California Santa Cruz] at 13:20 20 November 2014 but no activity in the Ames test, while 8 was active in both the rec-assay and Ames test. 4 ) Such a difference in mutagenicity might be correlated with the reduction potential of the nitro groups, on which an investigation is under way using polarography; the results will be published soon.…”

Scientific Opinion on the re‐evaluation of sorbic acid (E 200), potassium sorbate (E 202) and calcium sorbate (E 203) as food additives

“…The Panel also noted that potential reaction products that may result from the interaction of sorbic acid with nitrites and with ascorbic acid in the presence of iron salts were demonstrated to be mutagenic in vitro (Namiki et al, 1980;Kitano et al, 2002) and that there are certain food categories for which the use of these food additives (sorbic acid with ascorbic acid in the presence of iron salts or sorbic acid with nitrites) is permitted in parallel. However, these reaction products have been shown to be formed under optimal experimental conditions in an aqueous environment only and may not be formed to any major extent in food matrices.…”

“…In the study by Namiki et al (1980), the interaction products of sorbic acid (10 mM) and sodium nitrite (80 mM) at 60 °C for 30 minutes were ethylnitrolic acid (ENA), mainly produced at pH values of 3.5-5.0; 1,4-dinitro-2-methylpyrrole, produced maximally at pH 3.5; and compounds "B", 27 "F" 28 and other minor products, mainly produced at lower pH values (1.5) and not fully characterised in their chemical structure. Their genotoxicity was investigated in the Rec-assay with Bacillus subtilis and in an Ames reversion assay with Salmonella typhimurium tester strains TA98 and TA100 in the absence and presence of S9 metabolic activation.…”

“…Sorbic acid can be present with nitrite (natural or incorporated as a food additive) in some foods such as meat products. Sorbic acid may react with nitrite to produce compounds containing C-nitro, C-nitroso and N-nitro groups, yielding potentially mutagenic products such as 1,4-dinitro-2 methylpyrrole and ethylnitrolic acid (Namiki et al, 1980(Namiki et al, , 1981. Further studies on the reactivity of these products and their stability to a range of pH values identified the formation of the acetonitrile oxide, a compound with alkylating capabilities (Pérez-Prior et al, 2008, 2009).…”