S-Nitroso-N-acetylcysteine Generates Less Carcinogenic N-Nitrosamines in Meat Products than Nitrite

Adi Shpaizer, Amos Nussinovich, Joseph Kanner, Oren Tirosh

Research output: Contribution to journalArticlepeer-review

Abstract

Nitrite reacts with secondary amines to form N-nitrosamines (N-NA), which lead to gastrointestinal cancers. The aim of this study was to compare nitrite with S-nitrosocysteine (Cys-SNO) and S-nitroso-N-acetylcysteine (NAC-SNO) with respect to N-NA formation, which was evaluated by determining the conversion of N-methylaniline to Nnitrosomethylaniline. Under neutral and acidic pH conditions, N-NA formation rate was nitrite > Cys-SNO > NAC-SNO. In the presence of copper or nucleophiles, NAC-SNO generated much less N-NA than Cys-SNO. Nitrite and Cys-SNO produced higher amounts of N-NA in the presence of oxygen, whereas NAC-SNO was almost oxygen insensitive. In meat in the stomach medium, NAC-SNO produced much lower amounts of N-NA than other additives. In heated meat, Cys-SNO and NAC-SNO generated the nitrosyl-hemochrome pink pigment, better than nitrite. In conclusion, NAC-SNO was much less reactive for N-NA formation than nitrite and Cys-SNO in conditions relevant to meat production and stomach digestion.

Original languageAmerican English
Pages (from-to)11459-11467
Number of pages9
JournalJournal of Agricultural and Food Chemistry
Volume66
Issue number43
DOIs
StatePublished - 2018

Keywords

  • carcinogens
  • food safety
  • meat preservation
  • nitrite
  • reactive nitrogen species

All Science Journal Classification (ASJC) codes

  • General Chemistry
  • General Agricultural and Biological Sciences

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