2240 J. Agric. Food Chem., Vol. 47, No. 6, 1999
Gonza´lez-Mancebo et al.
Challis, B. C.; Lawson, A. J . The chemistry of nitroso com-
pounds. II. The nitrosation of phenol and anisole J . Chem.
Soc. (B) 1971, 770.
Mende, P.; Wacker, C.-D.; Preussmann, R.; Spiegelhalder B.
Nitrosation of the antimicrobial drug hexetidine: Nitros-
amines derived from triamine decomposition product. Food
Chem. Toxicol. 1993, 31, 53.
Mirvish, S. S. Role of N-nitroso compounds (NOC) and N-
nitrosation in etiology of gastric, esophageal, nasopharyn-
geal and bladder cancer and contribution to cancer of known
exposures to NOC. Cancer Lett. 1995, 93, 17.
Ohshima, H.; Friesen, M.; Malaveille, C.; Brouet, I.; Haute-
feuille, A.; Bartsch, H. Formation of direct-acting genotoxic
substances in nitrosated smoked fish and meat products:
Identification of simple phenolic precursors and phenyl-
diazonium ions as reactive products. Food Chem. Toxicol.
1989, 27, 193.
Pignatelli, B.; Scriban, R.; Descotes, G.; Bartsch, H. Modifying
effect of polyphenols and other constituents of beer on the
formation of N-nitroso compounds. J . Am. Soc. Brew. Chem.
1984, 42, 18.
Challis, B. C.; Higgins, R. J . The chemistry of nitroso com-
pounds. VII. The first “fast” proton transfer for an aromatic
nitrosation. J . Chem. Soc., Perkin Trans. 2 1973, 1597.
Connors, K. A. Chemical Kinetics. The Study of Reaction Rates
in Solution; VCH: New York, 1990; pp 292-298.
Davies, R.; Dennis, M. J .; Massey, R. C.; McWeeny, D. J . Some
effects of phenol- and thiol-nitrosation reactions on N-
nitrosamine formation. IARC Scientific Publication 19;
IARC: Lyon, France, 1978; pp 183-197.
Exner, O. Correlation Analysis of Chemical Data; Plenum:
New York, 1988; pp 105-111.
Ferna´ndez-Liencres, M. P.; Calle, E.; Gonza´lez-Mancebo, S.;
Casado, J .; Quintero, B. Nitrosation kinetics of phenolic
components of foods and beverages. Int. J . Chem. Kinet.
1997, 29, 119.
Garc´ıa-Prieto, J . C.; Mateos, R.; Calle, E.; Casado, J . Inhibition
of nitrosation by the reaction medium. J . Agric. Food Chem.
1998, 46, 3517.
Gonza´lez-Mancebo, S.; Calle, E.; Garc´ıa-Santos M. P.; Casado
J . Inhibition of nitrosation by steric hindrance. J . Agric.
Food Chem. 1997, 45, 334.
Haslam, E. Practical polyphenolics: from structure to molec-
ular recognition and physiological action; Cambridge Uni-
versity Press: Cambridge, U.K., 1998.
Pignatelli, B.; Descotes, G.; Barstch, H. Compose´s N-nitrose´s:
formation et effets biologiques. L’Actual. Chim. 1985, 33.
Rosenkranz, H. S.; Klopman, G.; Ohshima, H.; Bartsch, H.
Structural basis of the genotoxicity of nitrosatable phenols
and derivatives present in smoked food products. Mutation
Res. 1990, 230, 9.
Schofield, K. Aromatic Nitration; Cambridge University
Press: Cambridge, U.K., 1980.
Ibne-Rasa, K. M. The mechanism of nitrosodecarboxylation of
3,5-dibromo-4-hydroxy benzoic acid and nitrosodeprotona-
tion of 2,6-dibromophenol. J . Am. Chem. Soc. 1962, 84, 4962.
J ensen, J . Chlorophenols in the terrestrial environment. Rev.
Environ. Contam. Toxicol. 1996, 146, 25.
Senent, S. Cine´tica Qu´ımica; UNED: Madrid, 1986; Vol. III,
pp 54-58.
Shenoy, N. R.; Choughuley, A. S. U. Effect of certain plant
phenolics on nitrosamine formation. J . Agric. Food Chem.
1989, 37, 721.
Kato, T.; Kojima, K.; Hiramoto, K.; Kikugawa, K. DNA strand
breakage by hydroxyphenyl radicals generated from mu-
tagenic diazoquinone compounds. Mutation Res. 1992, 268,
105.
Kikugawa, K.; Kato, T. Formation of a mutagenic diazoquinone
by interaction of phenol with nitrite. Food Chem. Toxicol.
1988, 26, 209.
Kikugawa, K.; Kato, T.; Takeda, Y. Formation of a highly
mutagenic diazo compound from the bamethan-nitrite reac-
tion. Mutation Res. 1987, 177, 35.
Leffler, J . E.; Grunwald, E. Rates and Equilibria of Organic
Reactions; Dover: New York, 1989; pp 128-131.
Lijinsky, W. Chemistry and Biology of N-nitroso Compounds;
Cambridge Monographs on Cancer Research; Cambridge
University Press: Cambridge, 1992.
Lin, J .-K.; Lee, S.-F. Enhancement of the mutagenicity of
polyphenols by chlorination and nitrosation in Salmonella
typhimurium. Mutation Res. 1992, 269, 217.
Loeppky, R. N., Michejda, C. J ., Eds. Nitrosamine and Related
N-Nitroso Compounds. Chemistry and Biochemistry; ACS
Symposium Series No. 553; American Chemical Society:
Washington, DC, 1994a; pp xi-xii.
Loeppky, R. N.; Bao, Y. T.; Bae, J .; Yu, L.; Shevlin, G. Blocking
Nitrosamine Formation. Understanding the Chemistry of
Rapid Nitrosation. In Nitrosamine and Related N-Nitroso
Compounds. Chemistry and Biochemistry; Loeppky, R. N.,
Michejda, C. J ., Eds.; ACS Symposium Series No. 553;
American Chemical Society: Washington, DC, 1994b; pp
52-65.
Loeppky, R. N.; Singh, S. P.; Elomari, S.; Hastings, R.; Theiss,
T. E. Evidence for radical cations in linked mechanisms of
N,N-dialkyl aromatic amine nitration and nitrosative de-
alkylation. J . Am. Chem. Soc. 1998, 120, 5193.
Maruyama, K.; Tanimoto, I.; Goto, R. Studies on the Baudisch
reaction. I. The synthesis of o-nitrosophenols. J . Org. Chem.
1967, 32, 2516.
Siebert, K. J .; Troukhanova, N. V.; Lynn, P. Y. The nature of
polyphenol-protein interactions. J . Agric. Food Chem. 1996a,
44, 80.
Siebert, K. J .; Carrasco, A.; Lynn, P. Y. Formation of protein-
polyphenol haze in beverages. J . Agric. Food Chem. 1996b,
44, 1997.
Tummavuori, J .; Lumme, P. Protolysis of nitrous acid in
aqueous sodium nitrate and sodium nitrite solutions at
different temperatures. Acta Chem. Scand. 1968, 22, 2003.
Turney, T. A.; Wright, G. A. Nitrous acid equilibria in
perchloric acid. J . Chem. Soc. 1958, 2415.
Veibel, S. Nitration. I. Nitrosation of phenol; II. Nitration of
phenol. Chem. Ber. 1930, 63, 1577.
Wakabayashi, K.; Nagao, M.; Ochiai, M.; Tsuda, M.; Yamai-
zumi, Z.; Saitoˆ, H.; Sugimura, T. Presence of 1-methyl-
1,2,3,4-tetrahydro-â-carboline-3-carboxylic acids and tyramine
as precursors of mutagens in soya sauce after nitrite
treatment. In N-Nitroso Compounds: Occurrence, Biological
Effects and Relevance to Human Cancer; O’Neill, I. K., von
Borstel, R. C., Miller, C. T., Long, J ., Bartsch, H., Eds.; IARC
Scientific Publication No. 57; IARC: Lyon, 1984; pp 17-
24.
Wilcox, A. L.; Bao, Y. T.; Loeppky, R. N. Pyrroles as effective
agents for blocking amine nitrosation. Chem. Res. Toxicol.
1991, 4, 373.
Received for review October 8, 1998. Revised manuscript
received March 18, 1999. Accepted March 19, 1999. The
authors thank the Commission of the European Communities
for supporting the research reported in this article as part of
a project on the nitrosatable molecules present in foodstuffs.
S.G.-M., M.P.G.-S., and J .H.-B. thank the Spanish Ministerio
de Educacio´n y Cultura and Universidad de Salamanca for
Ph.D. grants.
McWeeny, R. Coulson’s Valence; Oxford University Press:
Oxford, U.K., 1979; pp 381-383.
J F981094N