W-Nitroso compounds

Certain species of Enterobacteriaceae, especially 0. proteus, could utilise nitrates as electron acceptors for anaerobic respiration, resulting in reduction of nitrate into nitrite. Nitrite further could possibly react with secondary amines present in the wort, forming (V-nitrosoamine (Figure 8.2). A -nitrosomines are carcinogenic in nature (Smith, 1994). Hence, a considerable amount of apparent total N-nitroso compounds (ATNCs) represents a possible risk to health, and consequently their concentration is strictly monitored and limited to 20 gg/1 (Maiguerite and Walker, 2002). Because of the risk of W-nitroso compounds, the Enterobacteriaceae species related to brewery environments are monitored. 

W. Lijinsky, Chemist and Biology of N-Nitroso Compounds, Cambridge University Press, Cambridge, U.K., 1992. 

W-Nitroso amine (Section 22.15) A compound of the type R,N—N=0. R may be alkyl or aryl groups, which may be the same or different. A-Nitroso amines are formed by nitrosation of secondary amines. 

Fong, Y. Y. Chan, W. C. "Environmental N-Nitroso Compounds Analysis and Formation," International Agency for Research on Cancer, Lyon, 1976, pp 461-464. 

Ivankovic, S. Preussmann, R. Schmahl, D. Zeller, J. W. N-Nitroso Compounds in the Environment, International Agency for Research on Cancer, Lyon, 1974, pp. 101-102. 

Mergens, W. J. Kamm, J. J. Newmark, H. L. Fiddler, W. Pensabene, J. "Environmental Aspects of N-Nitroso Compounds, International Agency for Research on Cancer,... 

Walker, E.A. Griciute, L. Castegnaro, M. Borzsonyl, M. Davis, W., Eds. N-Nitroso Compounds Analysis, Formation and Occurrence , vol. 31 Internatl. Agency for Research on Cancer Lyon, France, 1980... 

Lijinsky, W. and D. Schmal. 1978. Carcinogenesis by nitroso derivatives of methylcarbamate insecticides and other nitrosoamides in rats and mice. Pages 495-501 in E.A. Walker, M. Castenegro, L. Griciute, and R.E. Lyle (eds.). Environmental Aspects of N-nitroso Compounds. World Health Qrg., Int. Agency Res. Cancer, IARC Sci. Publ. 19. 

Joel F. Liebman, Mary Stinecipher Campbell and Suzanne W. Slayden D. Aliphatic Nitroso Compounds... 

Oberdorster E (2004) Manufactured nanomaterials (fullerenes, C60) induce oxidative stress in the brain of juvenile largemouth bass. Environ Health Pers 112 1058-1062 Oberdorster G, Sharp Z, Atudorei V, Elder A, Gelein R, Kreyling W, Cox C (2004) Translocation of inhaled ultrafine particles to the brain of rats. Inhal Toxicol 16 437-445 Odashima S (1980) Overview N-nitroso compounds as carcinogens for experimental animals and man. Oncology 37 282-286... 

Of trialkyl phosphites the most frequently used is triethyl phosphite (EtO)3P (M.W. 166.16, b.p. 156°, density 0.969) which combines with sulfur in thiiranes [291, 294] and gives alkenes in respectable yields. In addition, it can extrude sulfur from sulfides [295], convert a-diketones to acyloins [296], convert a-keto acids to a-hydroxy acids [297], and reduce nitroso compounds to hydroxylamines [298] Procedure 47, p. 111). 

W. R. Analytical determination of N-nitroso compounds in pesticides by the United States Environmental Protection Agency - A preliminary study. In Walker, E. A. Castegnaro, M. Griciute, L. Lyle, R. E., Eds. "Environmental Aspects of N-Nitroso Compounds" lARC Scientific Publication... 

Bishop,W.W. in "Environmental Aspects of N-nitroso Compounds" Walker, E.A., Castegnaro, M., ... 

Knaak, J.B., Leung, H.-W., Stott, W.T., Busch, J. Bilsky, J. (1997) Toxicology of mono-, di-, and triethanolamine. Rev. environ. Contam. Toxicol., 149, 1-86 Konishi, Y, Yokose, Y, Mori, Y, Yamasaki, H., Yamamoto, K., Nakajima, A. Denda, A. (1987) Lung carcinogenesis by V-nitrosobis(2-hydroxypropyl)amine-related compounds and their formation in rats. In Bartsch, H., O Neill, l.K. Schulte-Hermann, R., eds. Relevance ofN-nitroso Compounds to Human Cancer Exposures and Mechanisms (lARC Scientific Publications No. 84), Lyon, lARCPrexx, pp. 250-252... 

Spiegelhalder, B., Muller, J., Drasche, H. Preussmann, R. (1987) V-nitrosodiethanolamine excretion in metal grinders. In Bartsch, H., O Neill, I.K. Schulte-Hermaim, R., eds. The Relevance of N-Nitroso Compounds to Human Cancer Exposures and Mechanisms (lARC Scientific Publications No. 84), Lyon, lARCPrei i, pp. 550-552 Sterzel, W. Eisenbrand, G. (1986) V-nitrosodiethanolamine is activated in the rat to an ultimate genotoxic metabolite by sulfotransferase. J. Cancer Res. din.Oncol., Ill, 20-24 Sullivan, P.A., Eisen, E.A., Woskie, S.R., Kriebel, D., Wegman, D.H., Hallock, M.F., Hammond, S.K., Tolbert, P.E., Smith, T.J. Monson, R.R. (1998) Mortality studies of metalworking fluid exposure in the automobile industry Vt. A case-control study of esophageal cancer. Am. J. ind. Med., 34, 36 8... 

Mergens, W. J., Kamm, J. J., Newmark, H. L., Fiddler, W., and Pensabene, J. (1978). Alpha-tocopherol Uses in preventing nitrosamine formation. In Environmental Aspects of N-Nitroso Compounds (E. A. Walker, L. Griciute, M. Castegnaro, and R. E. Lyle, eds.), pp. 199-212. lARC Scientific Publication NO. 19. International Agency for Research on Cancer, Lyon, France. 

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