Reactivity of acrylamide as an alkylating agent: A kinetic approach

Journal of Physical Organic Chemistry

Volumn 23, Issue 2, 2010, Pages 171-175

  Céspedes Camacho, Isaac F ^a   Manso, José A ^a   Teresa Perez Prior M ^a   Gómez Bombarelli, Rafael ^a   González Pérez, Marina ^a   Calle, Emilio ^a   Casado, Julio ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Acrylamide; Alkylation reactions

Indexed keywords

ACRYLAMIDES; ADDUCT FORMATION; ALKYLATING AGENTS; ALKYLATION REACTIONS; DIELECTRIC CONSTANTS; DNA BASIS; EPIDEMIOLOGIC-STUDY; FOOD SCIENCE; GIBBS ENERGY; HUMAN CARCINOGEN; KINETIC APPROACH; RATE EQUATIONS;

ACTIVATION ENERGY; ALKYLATION; AMIDES; ENVIRONMENTAL PROTECTION AGENCY; MUTAGENS; PERMITTIVITY; REACTION RATES;

HYDROCARBONS;

EID: 76749142541     PISSN: 08943230     EISSN: 10991395     Source Type: Journal    
DOI: 10.1002/poc.1600     Document Type: Article

References (38)

1. M. Friedman, J. Agric. Food Chem. 2003, 51, 4504.
2. T. R. Fennell, S. C. Sumner, R. W. Snyder, J. Burgess, R. Spicer, W. Bridson, M. Friedman, Toxicol. Sci. 2005, 85, 447.
3. H. L. Pérez, H. K. Cheong, J. S. Yang, S. Osterman-Golkar, Anal. Biochem. 1999, 274, 59.
4. D. R. Doerge, G. Gamboa da Costa, L. P. McDaniel, M. I. Churchwell, N. C. Twaddle, F. A. Beland, Mutat. Res. 2005, 580, 131.
5. S. C. Sumner, T. Fennell, T. A. Moore, B. Chanas, B. I. Ghanayem, Chem. Res. Toxicol. 1999, 12, 1110.
6. B. I. Ghanayem, K. L. Witt, G. E. Kissling, L. Recio, Mutat. Res. 2005, 578, 284.
7. M. A. Friedman, L. H. Dulak, M. A. Stedham, Fundam. Appl. Toxicol. 1995, 27, 95.
8. R. J. Bull, M. Robinson, R. D. Laurie, G. D. Stoner, E. Greisiger, J. R. Meier, J. Stober, Cancer Res. 1984, 44, 107.
9. IARC. Acrylamide in: IARC Monographs on the Evaluation of Carcinogenic Risk to Humans: Some Industrial Chemicals, Vol.60. IARC, Lyon, France, 1994, pp. 389.
10. U.S. EPA. Assessment of Health Risk from Exposure to Acrylamide, Office of Toxic Substances, U.S. EPA, Washington, DC, (1990).
11. R. M. LoPachin, Neurotoxicology 2004, 25, 617.
12. A. Besaratinia, G. P. Pfeifer, Mutat. Res. 2005, 580, 31.
13. K. L. Dearfield, C. O. Abernathy, M. S. Ottley, J. H. Brantner, P. F. Hayes, Mutat. Res. 1988, 195, 45.
14. P. S. Spencer, H. H. Schaumburg, Canc. J. Neurol. Sci. 1974, 1, 152.
15. W. Lijinsky, A. Andrews, Teratogen. Carcinogen. 1980, 1, 259.
16. E. Tareke, P. Rydberg, P. Karlsson, S. Eriksson, M. Tornqvist, J. Agric. Food Chem. 2002, 50, 4998.
17. J. Knol, W. Van Loon, J. Linssen, A. L. Ruck, M. Van Boekel, A. Voragen, J. Agric. Food Chem. 2005, 53, 6133.
18. K. De Vleeschouwer, I. Van der Plancken, A. Van Loey, M. E. Hendrickx, Biotechnol. Prog. 2007, 23, 722.
19. R. V. Hedegaard, H. Frandsen, L. H. Skibsted, Food Chem. 2008, 108, 917.
20. D. S. Mottram, B. L. Wedzicha, A. T. Dodson, Nature 2002, 419, 448.
21. R. H. Stadler, I. Blank, N. Varga, F. Robert, J. Hau, P. A. Guy, S. Riediker, Nature 2002, 419, 449.
22. R. H. Stadler, F. Robert, S. Riediker, N. Varga, T. Davidek, S. Devaud, T. Goldmann, J. Hau, I. Blank, J. Agric. Food Chem. 2004, 52, 5550.
23. S. I. Martins, M. A. Van-Boekel, Food Chem. 2005, 90, 257.
24. P. Rydberg, S. Eriksson, E. Tareke, P. Karlsson, L. Ehrenberg, M. Tornqvist, J. Agric. Food Chem. 2003, 51, 7012.
25. M. Biedermann, A. Noti, S. Bidermann-Brem, V. Mozzetti, K. Grob, Mitt. Lebensm. Hyg. 2002, 93, 668.
26. J. H. Kim, J. J. Thomas, Bull. Environ. Contam. Toxicol. 1992, 49, 879.
27. S. E. Shepard, W. K. Lutz, Cancer Surv. 1989, 8, 401.
28. J. A. Manso, M. T. Pérez-Prior, M. P. García-Santos, E. Calle, J. Casado, Chem. Res. Toxicol. 2005, 18, 1161.
29. E. Fernández-Rodríguez, J. A. Manso, M. T. Pérez-Prior, M. P. García- Santos, E. Calle, J. Casado, Int. J. Chem. Kinet. 2007, 39, 591.
30. R. Gómez-Bombarelli, M. González-Pérez, M. T. Pérez-Prior, J. A. Manso, E. Calle, J. Casado, Chem. Res. Toxicol. 2008, 21, 1964.
31. J. A. Manso, M. T. Pérez-Prior, M. P. García-Santos, E. Calle, J. Casado, J. Phys. Org. Chem. 2008, 21, 932.
32. M. T. Pérez-Prior, J. A. Manso, M. P. García-Santos, E. Calle, J. Casado, J. Solution Chem. 2007, 37, 459.
33. M. T. Pérez-Prior, J. A. Manso, M. P. García-Santos, E. Calle, J. Casado, J. Agric. Food Chem. 2005, 53, 10244.
34. Joint Institute for Food Safety and Applied Nutrition (JIFSAN). http:// www.acrylamide-food.org
35. J. Casado, M. A. López-Quintela, F. M. Lorenzo-Barral, J. Chem. Educ. 1986, 63, 450.
36. K. A. Connors, Chemical kinetics, in The Study of Reaction Rates in Solution, VCH, New York, 1990, pp. 208-246.
37. J. J. Jungers, L. Sajus, I. Aguirre, D. Decrocq, L'analyse cinétique de la transformation chimique, Technip, Paris, 1968.
38. G. Åkerlöf, O. Short, J. Am. Chem. Soc. 1936, 58, 1241.