Catalytic effect of nitrosophenols on N-nitrosamine formation

  title={Catalytic effect of nitrosophenols on N-nitrosamine formation},
  author={R. Davies and D. McWeeny},
THE effect of phenolic compounds on the rate of nitrosation of secondary amines is not a simple one. Tannins inhibit nitrosamine formation1, but in suitable conditions gallic acid catalyses the nitrosation of diethylamine, the rate being dependent on pH and gallic acid concentration2. Some phenolic constituents of smoked foods3 inhibit nitrosation of morpholine at pH 3.0. Phenolic compounds react with nitrite at a much faster rate than do secondary amines4, but chlorogenic acid and 4… Expand
Effect of malondialdehyde on nitrosamine formation.
Abstract Several aldehydes associated with foodstuffs were investigated for their effect on the formation of N-nitrosodimethylamine and N-nitrosodiethylamine. Whereas glucose, furfural, benzaldehydeExpand
Effect of alcohols on nitrosamine formation.
The effects of the alcohols on nitrosation were different from their effects on azo-dye formation, which was inhibited by ethanol and isopropanol at both pH 3 and pH 5, and the reasons for enhancement at pH 5 are obscure. Expand
A study of the competitive nitrosations of pyrrolidine, ascorbic acid, cysteine and p‐cresol in a protein‐based model system
The effects of competitive C- and S-nitrosations on the formation of nitrosopyrrolidine were studied in a protein-based model system. The results obtained were compared with those of the analogousExpand
The catalysis of the N-nitrosation of secondary amines by nitrosophenols
Abstract p -Nitrosophenols and the structurally related compounds, p -nitroso- N -alkylanilines and p -nitroso- N -dialkylanilines, have been found to catalyse the N-nitrosation of pyrrolidine andExpand
Nitrate, nitrite and N -nitroso compounds: biochemistry, metabolism, toxicity and carcinogenicity
The addition of a nitroso group (−N=O) to a nitrogen atom is termed N-nitrosation: its product is an N-nitroso compound. These compounds include the nitrosamines (RR′−N−N=O), nitrosamides Open imageExpand
A study of the rates of the competitive nitrosations of pyrrolidine, p-cresol and L-cysteine hydrochloride.
The competitive nitrosations of pyrrolidine, p-cresol and L-cysteine hydrochloride were studied in aqueous solution under conditions which simulate those found in meat during processing, storage, cooking and gastric digestion. Expand
Contribution of wood smoke to in vivo formation of N-nitrosothiazolidine-4-carboxylic acid: initial studies.
  • W. Ikins, J. Gray, +4 authors D. J. Buckley
  • Chemistry, Medicine
  • Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
  • 1988
Alpha-Tocopherol was much less effective than ascorbate in blocking NTCA formation, and when smoked bacon, smoked Swiss cheese, and chicken barbecued with a sauce containing smoke flavouring were fed to rats along with nitrate, N TCA was again detected in the urine. Expand
A review of current literature on N-nitroso compounds in foods.
  • J. Hotchkiss
  • Chemistry, Medicine
  • Advances in food research
  • 1987
This chapter discusses the occurrence and formation of N-nitroso compounds in foods and other consumer products, and the relationship between the structure of a given N-Nitrosamine and the organ in which tumors develop. Expand
The occurence and formation of N-nitroso compounds in vivo
A method of analysis was developed for the measurement of total extractable N-nitroso compounds in biological fluids. The method was based on the selective chemical reduction of N-nitroso compoundsExpand
The effect of benzenediols and benzenetriols on the nitrosation of propranolol depends on the position of hydroxyl groups on the benzene ring.
The results of this study indicate that depending on the positions of hydroxyl groups on the benzene ring benzenediols and benzenetriols may inhibit or hasten nitrosation reactions. Expand


Nitrosation of phenols in smoked bacon
The studies of phenol nitrosation in smoked bacons are prompted to report by a recent suggestion that competitive nitrosating of phenolic residues may reduce the amount of nitrosamine formation. Expand
Rapid Nitrosation of Phenols and its Implications for Health Hazards from Dietary Nitrites
THE use of sodium nitrite as a food preservative is under close scrutiny because its presence may result in the formation of secondary N-nitrosamines, which are powerful carcinogens in laboratoryExpand
Possible cocarcinogenic effects of coffee constituents
It is reported here that readily oxidised phenolic compounds act as catalysts rather than inhibitors for N-nitrosamine formation from nitrite salts and secondary amines at gastric pH, which has important implications on the possible cocarcinogenic properties of several foodstuffs and beverages, including coffee. Expand