Formation of heterocyclic n-nitrosamines from the reaction of nitrite and selected primary diamines and amino acids Public Deposited

http://ir.library.oregonstate.edu/concern/graduate_thesis_or_dissertations/wh246v24g

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  • The reaction of several primary amines with nitrite was investigated with regard to the formation of N-nitrosamines. When reacted in a low moisture system at 160°C with a 1:2 molar ratio of amine to sodium nitrite, various primary amine hydrochloride salts were found to give rise to heterocyclic nitrosamines. The amines and yields of nitrosamines were as follows: putrescine, 22% nitrosopyrrolidine; cadaverine, 21.5% nitrosopiperidine; ornithine, 1% nitrosopyrrolidine and 3% nitrosoproline; lysine, 1% nitrosopiperidine and 2.5% nitrosopipecolic acid. Nitrosamine analysis was by gas chromatography and identification was confirmed by mass spectrometry. The analysis of the nitrosamino acids was facilitated by making the methyl ester derivatives. When the reactions were carried out in buffered solution at temperatures up to 100°C, the same products were identified except ornithine did not produce nitrosopyrrolidine and lysine did not produce nitrosopiperidine. The pH optimum for the formation of nitrosopyrrolidine was 3.8 and the pH optimuna for the production of nitrosopipecolic acid from lysine was 3.4. Substantial differences in nitrosamine yield were noted when various types of buffer were used. The effects of time and temperature were investigated with nitrosamines being produced at temperatures as low as 22°C. The concentration of nitrite influenced nitrosamine yield dramatically and the reaction rate appeared to be second order with respect to nitrite concentration. Theoretical yields of heterocyclic nitrosamines from primary diamines reacted with nitrite in buffer were as high as nine percent. On a comparative basis, yields of five-membered heterocyclic nitrosamines were higher than the six-membered ring compounds, and the amino acids gave higher yields of the respective nitrosamines than did the simple diamines. When butylamine was reacted with nitrite, dibutylnitrosamine was identified as a product. Yields were extremely low in solution, but as a high temperature-low moisture reaction, one percent of the nitrosamine was formed. A system similar to frying bacon was used to determine if putrescine could contribute to the formation of nitrosopyrrolidine in cooked bacon. Ground pork belly containing 200 ppm sodium nitrite was cooked to 177°C and the cooked meat, cooked-out fat, and cooking distillate were combined and analyzed for nitrosopyrrolidine. An average of 109 ppb nitrosopyrrolidine was detected without added putrescine. When 0.40% putrescine was added to the pork prior to cooking, an average of 321 ppb nitrosopyrrolidine was formed. In another set of cooking experiments, only the distillate was analyzed. Increased amounts of nitrosopyrrolidine were detected when the pork contained added putrescine or proline.
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