N-nitrosamines in foods

C R C Critical Reviews in Food Technology

Volumn 5, Issue 4, 1975, Pages 357-402

  Scanlan, Richard A ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84963198655     PISSN: 00079006     EISSN: None     Source Type: Journal    
DOI: 10.1080/10408397509527180     Document Type: Article

References (197)

1. Barnes, J. M. and Magee, P. N., Some toxic properties of dimethylnitrosamine, Br. J. Ind. Med., 11, 167, 1954.
2. Magee, P. N. and Barnes, J. M., The production of malignant primary hepatic tumors in the rat by feeding dimethylnitrosamine, Br. J. Cancer. 10, 114, 1956.
3. Ender, F., Harve, G. N., Madsen, R., Ceh, L., and Helgebostad, A., Studies on conditions under which N-nitrosodimethylamine is formed in herring meal produced from nitrite-preserved herring, Z. Tierphysiol. Tieremaehr. Futtermittelkd. 22, 181, 1967.
4. Ender, F., Harve, G., Helgebostad, A., Koppang, N., Madsen, R., and Ceh, L., Isolation and identification of a hepatotoxic factor in herring meal produced from sodium nitrite preserved herring, Naturwissenschaften, 51,637, 1964.
5. Rhoades, J. W. and Johnson, D. E., Method for the determination of N-nitrosamines in tobacco-smoke condensate, J. Natl. Cancer Inst., 48, 1841. 1972.
6. Hoffmann, D., Hecht, S. S., Ornaf, R. M., and Wynder, E. L., N'-nitrosonornicotine in tobacco, Science, 186, 265, 1974.
7. Druckrey, H., Preussmann, R., Ivankovic, S., and Schmaehl, D., Organotrope carcinogene Wirkungen bei 65 verschiedenen N-Nitroso-Verbindungen an BD-Ratten, Z. Krebsforsch., 69, 103, 1967.
8. Magee, P. N. and Barnes, J. M., Carcinogenic nitroso compounds, in Advances in Cancer Research, Vol. 10, Haddow, A. and Weinhouse, S., Eds. Academic Press, New York, 1967, 163.
9. Sander, J. and Schweinsberg, F., Wechselbeziehungen zwischen Nitrat, Nitrit und kanzerogenen N-Nitrosoverbindungen. 1. Mittenlung: nitrat, nitrit und nitrosierbare Aminoverbindungen der Nahrungs-, GenuB- und Arzneimittel, Chimie der N-Nitrosoverbindungen, Zentralbl. Bakteriol. [Orig. B.]. 156. 299, 1972.
10. Wolff, I. A. and Wasserman, A. E., Nitrates, nitrites, and nitrosamines, Science, 177, 15, 1972.
11. Sebranek, J. G. and Cassens, R. G., Nitrosamines: A Review, J. Milk Food Technol., 36, 76, 1973.
12. Pensabene, J. W., Fiddler, W., Dooley, C. J., Doerr, R. C., and Wasserman, A. E., Spectral and gas chromatographic characteristics of some N-nitrosamines, J. Agric. Food Client., 20, 274, 1972.
13. White, E. H., The chemistry of the N-alkyl-N-nitrosamides. I. Methods of preparation, J. Am. Chem. Soc, 77, 6008, 1955.
14. Fan, T. Y. and Tannenbaum, S. R., Stability of N-nitroso compounds, J. Food Sci., 37, 274, 1972.
15. Yang, K.W. and Brown, E.V., A sensitive analysis for nitrosamines, Anal. Lett., 5, 293, 1972.
16. Hoffmann, D. and Vais, J., Analysis of volatile N-nitrosamines in unaged mainstream smoke of cigarettes, presented at 25th Tobacco Chem. Res. Conf., Louisville, Ky., October 6 to 8, 1971.
17. Telling, G. M., A gas-liquid chromatographic procedure for the detection of volatile N-nitrosamines at the ten parts per billion level in foodstuffs after conversion to their corresponding nitramines, J. Chromatogr., 73, 79, 1972.
18. Ridd, J. H., Nitrosation, Diazotisation, and deamination.Q. Rev. Chem. Soc. Lond., 15,418, 1961.
19. Ingold, C. K., Substitution at hetero-elements, in Structure and Mechanism in Organic Chemistry, 2nd ed., Cornell University Press, Ithaca, N.Y., 1969, 611.
20. Challis, B. C. and Butler, A. R., Substitution at an amino nitrogen, in The Chemistry of the Amino Group, 1st ed., Patai, S., Ed., Interscience, New York, 1968, 277.
21. Kalatzis, E. and Ridd, J. H., Nitrosation, Diazotisation, and deamination. XII. The kinetics of N-nitrosation of N-methyl-aniline, J. Chem. Soc. (Lond.) (B), 529, 1966.
22. Taylor, T. W. J. and Price, L. S., The action of nitrous acid on amino-compounds. III. Dimethylamine, N-propylamine, and glycine ethyl ester, J. Chem. Soc. (Lond.), 2052, 1929.
23. Mirvish, S. S., Kinetics of dimethylamine nitrosation in relation to nitrosamine carcinogenesis, J. Natl. Cancer Inst., 44,633,1970.
24. Hantzsch, A. and Schumann, M., Zur kenntniss des diazotirungsprocesses. Ber. Dtsch. Chem. Ges., 32, 1691, 1899.
25. Hughes, E. D., Ingold, C. K., and Ridd, J. H., Nitrosation, Diazotisation, and deamination. II. Second and third-order Diazotisation of aniline in dilute perchloric acid, J. Chem. Soc, (Lond.), 65, 1958.
26. Hughes, E. D. and Ridd, J. H., Nitrosation, Diazotisation, deamination. III. Zeroth-order Diazotisation of aromatic amines in carboxylic acid buffers, J. Chem. Soc. (Lond.), 70, 1958.
27. Hammett, L. P., Physical Organic Chemistry, McGraw-Hill, New York, 1940,294.
28. Sander, J., Schweinsberg, F., and Menz, H. P., Untersuchungen uber die Entstehung cancerogener Nitrosamine im Magen, Hoppe-Seyler's Z. Physiol. Chem, 349, 1691,1968.
29. Mirvish, S. S., Kinetics of N-nitrosation reactions in relation to tumorigenesis experiments with nitrite plus amines or ureas, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 104.
30. Mirvish, S. S., Kinetics of nitrosamide formation from alkylureas, N-alkylurethans, and alkylguanidines: Possible implications for the etiology of human gastric cancer, J. Natl. Cancer Inst., 46, 1183, 1971.
31. Schmid, H., “Catalyticaliy polar” Substances, Z. Elektrochem., 43, 626, 1937.
32. Schmid, H. and Muhr, G., ber den Mechanismus der Diazotierung, Ber. Dtsch. Cliem. Ges., 70, 421, 1937.
33. Fan, T. Y. and Tannenbaum, S. R., Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite: Acceleration by thiocyanate and other anions, J. Agric. Food Chem. 21, 237, 1973.
34. Boyland, E., Nice, E., and Williams, K., The catalysis of nitrosation by thiocyanate from saliva, Food Cosmet. Toxicol., 9,639.1971.
35. Mirvish, S. S., Sams, J., Fan, T. Y., and Tannenbaum, S. R., Kinetics of nitrosation of the amino acids proline, Hydroxyproline, and sarcosine, J. Natl. Cancer Inst., 51, 1833, 1973.
36. Boyland, E., The effect of some ions of physiological interest on nitrosamine synthesis, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussman, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 124.
37. Fiddler, W., Pensabene, J. W., Kushnir, I., and Piotrowski, E. G., Effect of frankfurter cure ingredients on N-nitrosodimethylamine formation in a model system, J. Food Sci., 38, 714,1973.
38. Hildrum, K. I., Formation of N-nitrosamines from the nitrosation of spermidine and spermine, Ph.D. thesis, Oregon State University, Corvallis, 1975.
39. Frost, A. A. and Pearson, R. G., Kinetics and Mechanism, 2nd ed., John Wiley & Sons, New York, 1961, 150.
40. Keefer, L. K. and Roller, P. P., N-nitrosation by nitrite ion in neutral and basic medium, Science, 181, 1245, 1973.
41. Mirvish, S. S., Wallcave, L., Eagen, M., and Shubik, P., Ascorbate-nitrite reaction: Possible means of blocking the formation of carcinogenic N-nitroso compounds, Science, 177,65, 1972.
42. Fiddler, W., Piotrowski, E. G., Pensabene, J. W., Doerr, R. C., and Wasserman, A. E., Effect of sodium nitrite concentration on N-nitrosodimethylamine formation in frankfurters, J. Food Sci. 37, 668, 1972.
43. Fiddler, W., Pensabene, J. W., Piotrowski, E. G., Doerr, R. C., and Wasserman, A. E., Use of sodium ascorbate or erythorbate to inhibit formation of N-nitrosodimethylamine in frankfurters, J. Food Sci., 38, 1084, 1973.
44. Fan, T. Y. and Tannenbaum, S. R., Natural inhibitors of nitrosation reactions: The concept of available nitrite, J. Food Sci., 38,1067,1973.
45. Daim, H., Loewe, L., and Bunton, C. A., Uber die Oxydation von Ascorbinsaure durch Salpetrige Saure. Teil. 6. Ubersicht und Diskussion der Ergebnesse, Helv. Chim. Acta, 43, 320, 1960.
46. Bogovski, P., Castegnaro, M., Pignatelli, B., and Walker, E. A., The inhibiting effect of tannins on the formation of nitrosamines, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 127.
47. Challis, B. C., Rapid nitrosation of phenols and its implications for health hazards from dietary nitrites, Nature, 244, 466, 1973.
48. Fan, T. Y. and Tannenbaum, S. R., Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite. II. Rate enhancement in frozen solutions, J. Agric. Food Chem., 21, 967,1973.
49. Crosby, N. T., Foreman, J. K., Palframan, J. F., and Sawyer, R., Estimation of steam-volatile N-nitrosamines in foods at the 1kg level, Nature, 238, 342, 1972.
50. Fazio, T., Damico, J. N., Howard, J. W., White, R. H., and Watts, J., Gas chromatographic determination and mass spectrometric confirmation of N-nitrosodimethylamine in smoked-processed marine fish, J. Agric. Food Chem., 19, 250,1971.
51. Geuther, A., Ueber die Einwirkung von Salpetrigsaurem Kali auf Salzsaures Tri thylamin, Arch. Pharm. (Weinheim), 123,200, 1864.
52. Heintz, W., Ueber die Einwirkung des Salpetrigsauren Kali's auf Salzsaures Tri thylamin, und ber die Trennung des Diathylamins von Tri thylamin, Ann. Chem. Pharm., 138, 319, 1866.
53. Hein, G. E., The reaction of tertiary amines with nitrous acid,. J. Chem. Educ, 40, 181, 1963.
54. Smith, P. A. S. and Loeppky, R. N. Nitrosative cleavage of tertiary amines, J. Am. Chem. Soc, 89, 1147, 1967.
55. Fiddler, W., Pensabene, J. W., Doerr, R. C., and Wasserman, A. E., Formation of N-nitrosodimethylamine from naturally occurring quaternary ammonium compounds and tertiary amines, Nature, 236, 307,1972.
56. Schweinsberg, F. and Sander, J., Cancerogene Nitrosamine aus einfachen aliphatischen terti ren Aminen und Nitrit, Hoppe-Seyler's Z. Physiol. Chem., 353, 1671, 1972.
57. Scanlan, R. A., Lohsen, S. M., Bills, D. D., and Libbey, L. M., Formation of dimethylnitrosamine from dimethylamine and trimethylamine at elevated temperatures, J. Agric. Food Chem., 22, 149, 1974.
58. Lijinsky, W., Keefer, L., Conrad, E., and Bogart, R., Nitrosation of tertiary amines and some biologic implications, J Natl. Cancer Inst., 49, 1239, 1972.
59. Lijinsky, W., Reaction of drugs with nitrous acid as a source of carcinogenic nitrosamines, Cancer Res., 34, 255, 1974.
60. Greenblatt, M., Kommineni, V., Conrad, E., Wallcave, L., and Lijinsky, W., In Vivo conversion of phenmetrazine into its N-nitroso derivative, Nat. New Biol., 236, 25,1972.
61. Austin, A. T., The action of nitrous acid on aliphatic amines, Nature. 188,1086,1960.
62. Streitwieser, A., An interpretation of the reaction of aliphatic primary amines with nitrous acid, J. Org. Chem., 22, 861,1957.
63. Linnemann, E., Ueber die Darstellung der Fettalkohole aus ihren Anfangsgliedern, Ann. Chem. Pharm., 161, 15, 1872.
64. Meyer, V., Barbieri, J., and Forster, F., Untersuchungen uber Umlargerungen III, Ber. Dtsch. Chem. Ges., 10, 130, 1877.
65. Adamson, D. W. and Kenner, J., The decomposition of the nitrites of some primary aliphatic amines, J. Chem. Soc. (Lond.), 838, 1934.
66. Warthesen, J., Formation of heterocyclic N-nitrosamines from the reaction of nitrite and selected primary diamines and amino acids, Ph.D. thesis, Oregon State University, Corvallis, 1975.
67. von Demjanow, N., Einwirkung von Salpetriger Saure auf Tetramethylenediamine, Ber. Dtsch. Chem. Ges., 25, 912, 1892.
68. Lijinsky, W. and Epstein, S. S., Nitrosamines as environmental carcinogens, Nature, 225, 21, 1970.
69. Hildrum, K. I., Scanlan, R. A., and Libbey, L. M., Identification of 7-buteny!-(-propenyl)-nitrosamine, the principal volatile nitrosamine formed in the nitrosation of spermidine or spermine, J. Agric. Food Chem. in press.
70. M hler, K. and Hallermayer, E., Bildung von Nitrosaminen aus Lecithin und Nitrit, Z. Lebensm-Unters.-Forsch., 151-152, 1973.
71. Preussmann, R., Toxicity of nitrite and N-nitroso compounds, in Proc. Int. Symp. Nitrite Meat Prod., Zeist, Krol, B. and Tinbergen, B. J., Eds., Centre for Agricultural Publishing and Documentation, Pudoc, Wageingen, 1974, 217.
72. Druckrey, H., Specific carcinogenic and teratogenic effects of “indirect” alkylating methyl and ethyl compounds, and their dependency of stages of oncogenic developments, Xenobiotica, 3, 271,1973.
73. Druckrey, H., Preussmann, R., and Ivankovic, S., N-nitroso compounds in organotropic and transplacental carcinogenesis, Ann. N. Y. Acad. Sci., 163, 676, 1969.
74. Terracini, B.,Magee, R. N., and Barnes, J. M., Hepatic pathology in rats on low dietary levels of dimethylnitrosamine, Br. J. Cancer, 21,559, 1967.
75. Garcia, H. and Lijinsky, W., Studies of the tumorigenic effect in feeding of nitrosoamino acids and of low doses of amines and nitrite to rats, Z. Krebsforsch., 79, 141, 1973.
76. Greenblatt, M. and Lijinsky, W., Failure to induce tumors in Swiss mice after concurrent administration of amino acids and sodium nitrite J. Natl. Cancer Inst., 48, 1389, 1972.
77. Greenblatt, M., Kommineni, V. R., and Lijinsky, W., Null effect of concurrent feeding of sodium nitrite and amino acids to MCR rats, J. Natl. Cancer Inst., 50, 799, 1973.
78. Montesano, R. and Magee, P. N., Metabolism of dimethylnitrosamine by human liver slices in vitro, Nature, 228, 173, 1970.
79. Bogovski, P., Preussmann, R., and Walker, E. A., Eds., N-Nitroso Compounds: Analysis and Formation, International Agency for Research on Cancer, Scientific Publication No. 3, Lyon, France, 1972.
80. Fazio, T., Howard, J. W., and White, R., Multidetection method for determining volatile nitrosamines in foods, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 16.
81. Fazio, T., White, R. H., Dusold, R., and Howard, J. W., Nitrosopyrrolidine in cooked bacon, J. Assoc. Off. Anal. Chem., 56, 919, 1973.
82. Proc. Conf. N-Nitroso Compounds Analysis and Formation, Lyon, France, October, 1973, in press.
83. Krol, B. and Tinbergen, B. J., Eds., Proc. Int. Sym. Nitrite Meat Prod., Zeist. Centre for Agricultural Publishing and Documentation, Pudoc, Wageingen, 1974.
84. Eisenbrand, G. A., von Hodenberg, A., and Preussmann, R., Trace analysis of N-nitroso compounds. II. Steam distillation at neutral, alkaline and acid pH under reduced and atmospheric pressure, Z. Anal. Chem., 251, 22, 1970.
85. Telling, G. M., Bryce, T. A., and Althorpe, J. J., Use of vacuum distillation and gas chromatography mass spectrometry for determining low levels of volatile nitrosamines in meat products, J. Agric. Food Chem., 19, 937, 1971.
86. Telling, G. M., A gas-liquid chromatographic procedure for the detection of volatile n-nitrosamines at the ten parts per billion level in foodstuffs after conversion to their corresponding nitramines, J. Chromatogr., 73, 79, 1972.
87. Sen, N. P., Multidetection methods for determining volatile nitrosamines in foods, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 25.
88. Eisenbrand, G., Determination of volatile nitrosamines at low levels in food by acid-catalyzed denitrosation and formation of derivatives from the resulting amines, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R., and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 64.
89. Castegnaro, M., Pignatelli, B., and Walker, E. A., A rapid method for the semi-quantitative determination of volatile N-nitrosamines in alcoholic beverages. Analyst, 99, 156, 1974.
90. Fiddler, W., Doerr, R., Ertel, J., and Wasserman, A. E., Gas liquid chromatographic determination of N-nitrosodimethylamine in ham, J. Assoc. Off. Anal. Chem., 54, 1160, 1971.
91. Howard, J. W., Fazio, T., and Watts, J. O., Extraction and gas chromatographic determination of N-nitrosodimethylamine in smoked fish: application to smoked nitrite-treated chub, J. Assoc. Off. Anal. Chem., 53, 269, 1970.
92. Issenberg, P. and Tannenbaum, S. R., Approaches to the determination of volatile and non-volatile nitrosamines in foods and beverages, in N-Nitroso Compounds: Analysis and Formation, Bogovski, P., Preussmann, R. and Walker, E. A., Eds., Scientific Publication No. 3, International Agency for Research on Cancer, Lyon, France, 1972, 31.
93. Likens, S. T. and Nickerson, G. B., Detection of certain hop oil constituents in brewing products, Am. Soc. Brew. Chem. Proc, 5,1964.
94. Marquardt, P. and Hedler, L., ber das Vorkommen von Nitrosaminen in Weizenmehl, Arzneim.Forsch., 16, 778, 1966.
95. Eisenbrand, G., Spaczynski, K., and Preussmann, R., Spurenanalyse von N-Nitroso-Verbindugen III. Quantitative D nnschichtchromatographie von Nitrosaminen, J. Chromatogr., 51,503, 1970.
96. Wasserman, A. E., Fiddler, W., Doerr, E. C., Osman, S. F., and Dooley, C. J., Dimethylnitrosamine in frankfurters, Food Cosmet. Toxicol, 10,681, 1972.
97. Newell, J. E. and Sisken, H. R., Determination of nitrosodimethylamine in the low parts per billion, J. Agric. Food Chem., 20, 7.11, 1972.
98. Preussmann, R., Neurath, G., Wulf-Lorentzen, G., Daiber, D., and Hengy, H., Anfarbemethoden und Dunnschicht-chromatographie von organischen N-nitroso-Verbindungen, Z. Anal. Chem. 202, 187, 1964.
99. Sen, N. P. and Dalpe, C, A simple thin-layer chromatographic technique for the semiquantitative determination of volatile nitrosamines in alcoholic beverages. Analyst, 97, 216, 1972.
100. Cox, G. B., Estimation of volatile N-nitrosamines by high-performance liquid chromatography, J. Chromatogr. 83, 471,1973.
101. Heyns, K. and R per, H., Ein Spezifisches Analytisches Nachweisverfahren fur Nitrosamine durch Kombination von Gaschromatographie mit der Massenspecktrometrie, Tetrahedron Lett., 10, 737, 1970.
102. Heyns, K. and Koch, H., Zur Frage der Entstehung von Nitrosaminen bei der Reaktion von Monosacchanden mit Ammosuaren (Maillard-Reaktion), Tetrahedron Lett., 10, 741, 1970.
103. Saxby, M. J., The separation of volatile N-nitrosamines and pyrazines Anal. Lett. 3. 397, 1970.
104. Essigmann, I.M. and Issenberg, P., Gas chromatographic determination of volatile nitrosamines in foods, J. Food Sci. 37,684, 1972.
105. Rhoades, J. W. and Johnson, D. E., Gas-chromatography and selective detection of N-nitrosamines, J. Chromatogr. Sci., 8,616, 1970.
106. Scanlan, R. A. and Libbey, L. M., N-nitrosamines not identified from heat induced D-glucose/alanine reactions, J. Agric. Food Chem., 19, 570, 1971.
107. Gough, T. A. and Webb, K. S., A method for the detection of traces of nitrosamines using combined gas chromatography and mass spectrometry, J. Chromatogr., 79, 57, 1973.
108. Foreman, J. K., Palframan, J. F., and Walker, E. A., Gas chromatographic determination of N-alkyl nitrosamines, Nature, 225, 554, 1970.
109. Mosier, A. R. and Andre, C. E., Direct gas chromatographic analysis of aqueous solutions of aliphatic N-nitrosamines, Anal. Chem., 45, 372, 1973.
110. Daiber, D. and Preussmann, R., Quantitative colorimetrische Bestimmung organischer N-nitroso-Verbindungen durch photochemische Spaltung der Nitrosaminbindung, Z. Anal. Chem., 206, 344, 1964.
111. Sander, J., Ein Methode zum Nachweis von Nitrosaminen, Hoppe-Seyler's Z. Physiol. Chem., 348, 852, 1967.
112. Fan, T. V. and Tannenbaum, S. R., Automatic colorimetric determination of N-nitroso compounds, J. Agric. Food Chem., 19, 1267, 1971.
113. Eisenbrand, G. and Preussmann, R., Elne neue Methode zur kolorimetrischen Bestimmung von Nitrosaminen nach Spaltung der N-nitrosogruppe mit Brom wasserst off in Eisessig, Arzneim.-Forsch., 20, 1513, 1970.
114. Ender, F. and Ceh, L., Conditions and chemical reaction mechanisms by which nitrosamines may be formed in biological products with reference to their possible occurrence in food products, Z. Lebensm.-Unters. -Forsch., 145, 133,1971.
115. Devik, O. G., Formation of N-nitrosamines by the Maillard Reaction, Acta Chem. Scand., 21, 2302, 1967.
116. Walters, C. L., Johnson, E. M., and Ray, N., Separation and detection of volatile and non-volatile N-nitrosamines, Analyst. 95,485, 1970.
117. Palframan, J. F., Macnab, J., and Crosby, N. T., An elevation of the alkali flame ionization detector and the Coulson electrolytic conductivity detector in the analysis of N-nitrosamines in foods, J. Chromatogr., 76, 307, 1973.
118. Alliston, T. G., Cox, G. B.,and Kirk, R. S., The determination of steam-volatile N-nitrosamines in foodstuffs by formation of electron-capturing derivatives from electrochemically derived amines, Analyst, 97, 915, 1972.
119. Sen, N. P., Gas-liquid chromatographic determination of dimethylnitrosamine as dimethylnitramine at picogram levels, J. Chromatogr., 53, 301, 1970.
120. Althorpe, J., Goddard, D. A., Sissons, D. J., and Telling, G. M., The gas chromatographic determination of nitrosamines at the picogram level by conversion to their corresponding nitramines, J. Chromatogr., 53, 371, 1970.
121. Dooley, C, J., Wasserman, A. E., and Osman, S., A contaminant in N-nitrosodimethylamine confirmation by high resolution mass spectrometry,J. Food Sci., 38, 1096, 1973.
122. Gough, T. A. and Webb, K. S., The use of a molecular separator in the determination of trace constituents by combined gas chromatography and mass spectrometry,J. Chromatogr., 64, 201, 1972.
123. Walters, C. L., Fueggle, D. G., and Lunt, T. G., The determination of total non-volatile nitrosamines in microgram amounts, in Proc. Int. Symp. Nitrite Meat Prod., Zeist, Krol, B. and Tinbergen, B. J., Eds., Centre for Agricultural Publishing and Documentation, Pudoc, Wageningen, 1974, 53.
124. Lunt, T. G., Fueggle, D. G., and Walters, C. L., The estimation of total non-volatile nitrosamines and nitrosamides in microgram amounts. Anal. Lett., 6, 369, 1973.
125. Fine, D. H., Rufeh, F., and Lieb, D., Group analysis of volatile and non-volatile N-nitroso compounds,Nature, 247, 309, 1974.
126. Fiddler, W., Kushnir, I., Feinberg, J., Piotrowski, E. G., and Wasserman, A. E., Isolation and identification of nitrosoproline in uncooked bacon, Presented at the 34th Annual IFT Meeting, New Orleans, May 1974.
127. Williams, A. A., Timberlake, C. F., Tucknott, O. G., and Patterson, R. L. S., Observations on the detection of dimethyl- and diethyl-nitrosamines in foods with particular reference to alcoholic beverage, J. Sci. Food Agr ‘C, 22, 431,1971.
128. Christiansen, L. N., Johnston, R. W., Kautter, D. A., Howard, J. W., and Aunan, W. J., Effect of nitrite and nitrate on toxin production by Clostridium botulinum and on nitrosamine formation in perishable canned comminuted cured meat. Appl. Microbiol., 25, 357, 1973.
129. Hustad, G. O., Cerveny, J. G., Trenk, H., Deibel, R. H., Kautter, D. A., Fazio, T., Johnston, R. W., and Kolari, O., Effect of sodium nitrite and sodium nitrate on botulinal toxin production and nitrosamine formation in wieners, Appl. Microbiol., 26, 22, 1973.
130. Fiddler, W., Pensabene, J. W., Fagan, J. C., Thorne, E. J., Piotrowski, E. G., and Wasserman, A. E., The role of lean and adipose tissue on the formation of nitrosopyrrolidine in fried bacon,J. Food Sci., 39, 1070, 1974.
131. Sen, N. P., Smith, D. C., Schwinghamer, L., and Hawsam, B., Formation of nitrosamines in nitrite-treated fish, Can. Inst. Food Technol. J., 3,66, 1970.
132. Fazio, T., White, R. H., and Howard, J. W., Analysis of nitrite- and/or nitrate-processed meats for N-nitrosodimethylamine, J. Assoc. Off. Anal. Chem., 54, 1157, 1971.
133. Sen, N. P., Schwinghamer, L. A., Donaldson, B. A., and Miles, W. F., N-nitrosodimethylamine in fish meal, J. Agric. Food Chem., 20, 1280, 1972.
134. Sen, N. P., The evidence for the presence of dimethylnitrosamines in meat products, Food Cosmet. Toxicol, 10, 219,1972.
135. Panalaks, T., Iyengar, J. R., and Sen, N. P., Nitrate, nitrite and dimethylnitrosamine in cured meat products, J. Assoc. Off. Anal. Chem., 56, 621, 1973.
136. Sen, N. P., Donaldson, B., Iyengar, J. R., and Panalaks, T., Nitrosopyrrolidine and dimethylnitrosamine in bacon, Nature, 241,473, 1973.
137. Sen, N. P., Miles, W. F., Donaldson, B., Panalaks, T., and Iyengar, J. R., Formation of nitrosamines in a meat curing mixture,Nature, 245, 104, 1973.
138. Panalaks, T., Iyengar, J. R., Donaldson, B. A., Miles, W. F., and Sen, N. P., Further survey of cured meat products for volatile N-nitrosamines, J. Assoc. Off. Anal. Chem., 57, 806, 1974.
139. Sen, N. P., Iyengar, J. R., Donaldson, B. A., and Panalaks, T., Effect of sodium nitrite concentration on the formation of nitrosopyrrolidine and dimethylnitrosamine in fried bacon, J. Agric. Food Chem., 22, 540,1974.
140. Pensabene, J. W., Fiddler, W., Gates, R. A., Fagan, J. C., and Wasserman, A. E., Effect of frying and other cooking conditions on nitrosopyrrolidine formation in bacon, J. Food Sci., 39, 314,1974.
141. Seiler, N., Identification and quantitation of amines by thin-layer chromatography,J. Chromatogr., 63, 97, 1971.
142. Narasimhachari, N., Spaide, J., and Heller, B., Gas-liquid chromatographic and mass spectrometric studies on trimethylsilyl derivatives of N-methyl- and N,N-dimethyltryptamines, J. Chromatogr. Sci., 9,502, 1971.
143. Zeman, A. and Wirotama, I.P.G., Identifiziering von Aminen. II. Capillar-Gas-Chromatographie-Massenspektrometrie (GC-MS) von Trifluoracetylderivaten (TFA-Amine), Z. Anal. Chem., 247, 158, 1969.
144. Anggard, E. and Sedvall, G., Gas chromatography of catecholamine metabolites using electron capture detection and mass spectrometry, Anal. Chem., 41, 1250, 1969.
145. Miller, A., III, Scanlan, R. A., Lee, J. S., and Libbey, L. M., Quantitative and selective gas chromatographic analysis of dimethyl-and trimethylamine in fish, J. Agric. Food Chem., 20, 709, 1972.
146. Miller, A., III., Scanlan, R. A., Libbey, L. M., Petropakis, H., and Anglemier, A. F., Quantitative determination of dimethyl-and trimethylamine in fish protein concentrate, J. Agric. Food Chem., 21,451, 1973.
147. Gulan, M. P., Measurement of dimethylamine and trimethylamine in Dungeness crab, Cancer magist er, M.S. thesis, Oregon State University, Corvallis, 1973.
148. Miller, A., III, Scanlan, R. A., Lee, J. S., and Libbey, L. M., Volatile compounds produced in ground muscle tissue of canary rockfish (Sebastes pinniger) stored on ice, J. Fish Res. Board Can., 29, 1125, 1972.
149. Code of Federal Regulations, Title 21, Sec. 121.1063, Sec. 121. 1064, Sec. 121.1230, and Sec. 121.13 (revised as of April 1, 1974).
150. Code of Federal Regulations, Title 9, Sec. 318.7 (revised as of Jan. 1, 1974).
151. Bard, J. and Townsend, W. E., Meat curing, in The Science of Meat and Meat Products, Price, J. F. and Schweigen, B. S., Eds., W. H. Freeman & Co., San Francisco, 1971, 452.
152. Bailey, M. E. and Swain, J. W., Influence of nitrite on meat flavor, Proc Meat Industry Research Conf, American Meat Institute Foundation, Chicago, 1973, 29.
153. Wasserman, A. E., Nitrite and the flavor of cured meat II, in Proc. Int. Symp. Nitrite Meat Prod., Zeist, Krol, B. and Tinbergen, B. J., Eds., Centre for Agricultural Publishing and Documentation, Pudoc, Wageningen, 1974, 173.
154. Cho, I. C. and Bratzier, L. J., Effect of sodium nitrite on flavor of cured pork, J. Food Sci., 35, 668, 1970.
155. Wasserman, A. E. and Talley, F., The effect of sodium nitrite on the flavor of frankfurters, J. Food Sci., 37, 536, 1972.
156. Simon, S., Ellis, D. E., MacDonald, B. D., Miller, D. G., Waldman, R. C., and Westerberg, D. O., Influence of nitrite and nitrate curing ingredients on quality of packaged frankfurters, J. Food Sci., 38,919, 1973.
157. Mottram, D. S. and Rhodes, D. N., Nitrite and the flavour of cured meat I., in Proc. Int. Symp. Nitrite Meat Prod., Zeist, Krol, B. and Tinbergen, B. J., Eds., Centre for Agricultural Publishing and Documentation, Pudoc, Wageningen, 1974, 161.
158. Skjelkvale, R., Tjaberg, T., and Valland, M., Comparison of salami sausage produced with and without addition of sodium nitrite and sodium nitrate, J. Food Sci., 39, 520, 1974.
159. Cross, C. K. and Ziegler, P., A comparison of the volatile fractions from cured and uncured meat, J. Food Sci., 30, 610, 1965.
160. Swain, J. W., Volatile flavor constituents of pork cured with and without nitrite, Ph.D. thesis, University of Missouri, Columbia, 1972.
161. Westerberg, D. O., Cured meat flavor and the role of nitrite in its development, in Proc. 26th Annu. Reciprocal Meat Conf. A.M.S.A., Pennsylvania State University, National Livestock and Meat Board, Chicago, 1973,45.
162. Schuck, P. and Wellford, H., Botulism and nitrites, Science, 180, 1322, 1973.
163. Rust, R. E., Here's what the future holds for meat curing, Natl. Provis., August 31, 1974, 16.
164. Lijinsky, W., Nitrites in foods, Science, 182, 1194, 1973.
165. Christiansen, L. N., Tompkin, R. B., Shaparis, A. B., Kueper, T. V., Johnston, R. W., Kautter, D. A., and Kolari, O. J., Effect of sodium nitrite on toxin production by Clostridium botulinum in bacon, Appl. Microbiol, 27, 733, 1974.
166. Collins-Thompson, D. L., Chang, P. C., Davidson, C. M., Larmond, E., and Pivnick, H., The effect of nitrite and storage temperature on the organoleptic quality and toxinogenesis by Clostridium botulinum in vacuum-packaged bacon, J. Food Sci., 39, 607,1974.
167. Greenberg, R. A., Tompkin, R. B., Bladel, B. O., and Kittaka, R. S., Incidence of mesophilic Clostridium spores in raw pork, beef, and chicken in processing plants in the United States and Canada, Appl. Microbiol., 14, 789, 1966.
168. Taclindo, C, Midura, T., Nygaard, G. S., and Bodily, H. L., Examination of prepared foods in plastic packages for Clostridium botulinum, Appl. Microbiol, 15,426, 1967.
169. Insalata, N. F., Witzeman, S. J., Fredericks, G., and Sunga, F. C. A., Incidence study of spores of Clostridium botulinum in convience foods, Appl. Microbiol, 17, 542, 1969.
170. Abrahamsson, K. and Riemann, H., Prevalence of Clostridium botulinum in semi-preserved meat products, Appl. Microbiol, 21,543, 1971l
171. Bowen, V. C., Cerveny, J. G., and Deibel, R. H., Effect of sodium ascorbate and sodium nitrite on toxin formation of Clostridum botulinum in wieners, Appl. Microbiol, 27, 605, 1974.
172. Tannenbaum, S. R., Sinskey, A. J., Weisman, M., and Bishop, W., Nitrite in human saliva. Its possible relationship to nitrosamine formation, J. Natl. Cancer Inst., 53, 79, 1974.
173. Kolari, O. E. and Aunan, W. J., The residual levels of nitrite in cured meat products, Meat Science Review (American Meat Institute Foundation), 6, 27, 1972.
174. Anonymous, The use of nitrate and nitrite in the meat industry, Meat Science Review (American Meat Institute Foundation), 5, 1, 1971.
175. Nordin, H. R., The depletion of added sodium nitrite in ham, Can. Inst. Food Technol. J., 2, 79, 1969.
176. Mira, A. and Hoffman, K., ber den vergleib von Nitrit in Fleischwaren, Fleischwirtschaft, 10, 1361, 1969.
177. Woolford, G., Casselden, R. J., and Walters, C. L., Gaseous products of the interaction of sodium nitrite with porcine skeletal muscle, J. Biochem., 130, 82,1972.
178. Olsman, W. J., About the mechanism of nitrite loss during storage of cooked meat products, in Proc. Int. Symp. Nitrite Meat Prod., Zeist, Centre for Agricultural Publishing and Documentation, Pudoc, Wageningen, 1974, 129.
179. Sebranek, J. G., Cassens, R. G., Hoekstra, W. G., and Winder, W. C., 15N tracer studies of nitrite added to a comminuted meat product, J. Food Sci, 38, 1220, 1973.
180. Fox, J. B. and Nicholas, R. A., Nitrite in meat. Effect of various compounds on loss of nitrite, J. Agric. Food Chem., 22, 302, 1974.
181. Archer, M. C., Gark, S. D., Thilly, J. E., and Tannenbaum, S. R., Environmental nitroso compounds: Reaction of nitrite with creatine and creatinine, Science, 174, 1341, 1971.
182. Knowles, M. E., McWeeny, D. J., Couchman, L., and Thorogood, M., Interaction of nitrite with proteins at gastric pH, Nature, 247, 288, 1974.
183. Knowles, M. E., Gilbert, J., and McWeeny, D. J., Nitrosation of phenols in smoked bacon, Nature, 249, 672, 1974.
184. Issenberg, P. and Virk, M., Inhibition of morpholine nitrosation by some phenolic wood smoke components, presented at the 168th American Chemical Society National Meeting, Atlantic City, New Jersey, September 1974.
185. Knowles, M. E., Gilbert, J., and McWeeny, D. J., C-Nitrosation products in food, Presented at the IV International Congress of Food Science and Technology, Madrid, Spain, September 1974.
186. Code of Federal Regulations, Title 21, Sec. 121.1164 (revised as of April 1, 1974).
187. Scanlan, R. A., unpublished data.
188. Collins-Thompson, D. L., Sen, N. P., Aris, B., and Schwinghamer, L., Non-enzymatic in vitro formation of nitrosamines by bacteria isolated from meat products, Can. J. Microbiol, 18, 1968, 1972.
189. Ayanaba, A. and Alexander, M., Microbial formation of nitrosamines in vitro. Appl. Microbiol, 25, 862, 1973.
190. Sander, J., Nitrosaminsynthese durch Bakterien, Hoppe-Seyler's Z. Physiol. Chem., 349, 429, 1968.
191. Hawksworth, G. M. and Hill, M. J., Bacteria and the N-nitrosation of secondary amines, Br. J. Cancer, 25, 520, 1971.
192. Hawksworth, G. and Hill, M. J., The formation of nitrosamines by human intestinal bacteria, Biochem. J., 122, 28, 1971.
193. Sen, N. P., Miles, W. F., Donaldson, B., Panalaks, T., and Iyengar, J. R., Formation of nitrosamines in a meat curing mixture, Nature, 245, 104, 1973.
194. Herring, H. K., Effect of nitrite and other factors on the physico-chemical characteristics and nitrosamine formation in bacon, Proc. Meat Industry Research Conf., American Meat Institute Foundation, Chicago, 1973, 47.
195. Lewin, D. N., How to calculate heat processes, Food Eng., N.Y., March 1962, 87.
196. Huxel, E. T., Scanlan, R. A., and Libbey, L. M., Formation of N-nitrosopyrrolidine from pyrrolidine ring containing compounds at elevated temperatures, J. Agric. Food Chem., 22, 698, 1974.
197. Bills, D. D., Hildrum, K. I., Scanlan, R. A., and Libbey, L. M., Potential precursors of N-nitrosopyrrolidine in bacon and other fried foods,J. Agric. Food Chem., 21, 876, 1973.