Gas chromatographic-mass spectrometric analysis of acrylamide and acetamide in cigarette mainstream smoke after on-column injection

Journal of Chromatographic Science

Volumn 46, Issue 7, 2008, Pages 659-663

  Diekmann, Joerg ^a   Wittig, Arno ^a   Stabbert, Regina ^b  

^a Philip Morris Research Laboratories GmbH   (Germany)

^b Philip Morris Products SA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 49649088914     PISSN: 00219665     EISSN: None     Source Type: Journal    
DOI: 10.1093/chromsci/46.7.659     Document Type: Article

References (45)

1. International agency for Research on Cancer (IARC) (2006): http://monographs.iarc.fr/ENG/Classification/Listagentscasnos.pdf.
2. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 60. Some Industrial Chemicals. International Agency for Research on Cancer, Lyon, 1994, pp. 389-433.
3. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Vol. 71. Re-evaluation of Some Organic Chemicals, Hydrazine, and Hydrogen Peroxide. International Agency for Research on Cancer, Lyon, 1999, pp. 1211-1221.
4. M. Friedman. Chemistry, biochemistry, and safety of acrylamide. A review. J. Agric. Food Chem. 51: 4504-4526 (2003).
5. E. Dybing, P.B. Farmer, M. Andersein, T.R. Fennell, S.P.D. Lalljie, D.J.G. Müller, S. Olin, B.J. Petersen, J. Schlatter, G. Scholz, J.A. Scimeca, N. Slimani, M. Törnqvist, S. Tuijtelaars, and P. Verger. Human exposure and internal dose assessments of acrylamide in food. Food Chem. Toxicol. 43: 365-410 (2005).
6. E. Bergmark, C.J. Calleman, and L.G. Costa. Formation of hemoglobin adducts of acrylamide and its epoxide metabolite glycidamide in the rat. Toxicol. Appl. Pharmacol. 111: 352-363 (1991).
7. E. Bergmark. Hemoglobin adducts of acrylamide and acrylonitrile in laboratory workers, smokers and nonsmokers. Chem. Res. Toxicol. 10: 78-84 (1997).
8. S. Thielen, M. Baum, M. Hoffmann, R.N. Loeppky, and G. Eisenbrand. Genotoxicity of glycidamide in comparison to (±)-anti-benzo[a]pyrene-7,8- dihydrodiol-9,10-epoxide and alpha-acetoxy-N-nitroso-diethanolamine in human blood and in mammalian V79-cells. Mol. Nutr. Food Res. 50: 430-436 (2006).
9. M. Jägerstad and K. Skog. Genotoxicity of heat-processed foods. Mutat. Res. 574: 156-172 (2005).
10. E.A. Smith and F.W. Oehme. Acrylamide and polyacrylamide: A review of production, use, environmental fate and neurotoxicity. Rev. Environ. Health 9: 215-228 (1991).
11. E. Tareke, P. Rydberg, P. Karlsson, S. Eriksson, and M. Törnqvist. A Cooking Carcinogen? Chem. Res. Toxicol. 13: 517-522 (2000).
12. J. Rosèn and K.-E. Hellenäs. Analysis of acrylamide in cooked foods by liquid chromatography tandem mass spectrometry. The Analyst 127: 880-882 (2002).
13. D. Taeymans, J. Wood, P. Ashby, I. Blank, A. Studer, R.H. Stadler, P. Gondé, P. Van Eijck, S. Lalljie, H. Lingnert, M. Lindblom, R. Matissek, D. Tallmdge, D. Müller, S. Thompson, J. O'Brien, T. Whitmore, and D. Silvani. A review of acrylamide: An industry perspective on research, analysis, formation, and control. Crit. Rev. Food Sci. Nutr. 44: 323-347 (2004).
14. R.H. Stadler, I. Blank, N. Varga, F. Robert, J. Hau, P. A. Guy, M.C. Robert, and S. Riediker. Acrylamide from Maillard reaction products. Nature 419: 449-50 (2002).
15. D.S. Mottram, B.L. Wedzicha, and A.T. Dodson. Acrylamide is formed in the Maillard reaction. Nature 419: 448-449 (2002).
16. A. Yasuhara, Y. Tanaka, M. Hengel, and T. Shibamoto. Gas chromatographic investigation of acrylamide formation in browning model systems. J. Agric. Food Chem. 51: 3999-4003 (2003).
17. J.N. Schumacher, C.R. Green, F.W. Best, and M.P. Newell. Smoke composition. An extensive investigation of the water-soluble portion of cigarette smoke. J. Agric. Food Chem. 25: 310-320 (1977).
18. E.L. White, M.S. Uhrig, T.J. Johnson, B.M. Gordon, R.D. Hicks, M.F. Borgerding, W.M. Coleman III, and J.F. Elder, Jr. Quantitative determination of selected compounds in a Kentucky 1R4F reference cigarette smoke by multidimensional gas chromatography and selected ion monitoring-mass spectrometry. J. Chrom. Sci. 28: 393-399 (1990).
19. J.D. deBethizy, M.F. Borgerding, D.J. Doolittle, J.H. Robinson, K.T. McManus, C.A. Rahn, R.A. Davis, G.T. Burger, J.R. Hayes, J.H. Reynolds, and A.W. Hayes. Chemical and biological studies of a cigarette that heats rather than burns tobacco. J. Clin. Pharmacol. 30: 755-763 (1990).
20. H.L. Pérez and S. Ostermann-Golkar. A sensitive gas chromatographic-tandem mass spectrometric method for the detection of alkylating agents in water: Application to acrylamide in drinking water, coffee and snuff. Analyst 128: 1033-1036 (2003).
21. M. Urban, D. Kavvadias, K. Riedel, G. Scherer, and A.R. Tricker. Urinary mercapturic acids and a hemoglobin addduct for the dosimetry of acrylamide exposure in smokers and nonsmokers. Inhal. Toxicol. 18: 831-839 (2006).
22. T. Wenzl, B. De La Calle, and E. Anklam. Analytical methods for the determination of acrylamide in food products: A review. Food Addit. Contam. 20: 885-902 (2003).
23. R.H. Stadler and G. Scholz. Acrylamide: An update on current knowledge in analysis, levels in food, mechanisms of formation, and potential strategies of control. Nutr. Rev. 62: 449-467 (2004).
24. A.F. Lagalante and M.A. Felter. Silylation of acrylamide for analysis by solid phase microextraction-gas chromatography-ion-trap mass spectrometry. J. Agric. Food Chem. 52: 3744-3748 (2004).
25. Y. Zhang, G. Zhang, and Y. Zhang. Occurrence and analytical methods of acrylamide in heat-treated foods. Review and recent developments. J. Chromatogr. A 1075: 1-21 (2005).
26. T. Wenzl, B. De La Calle, R. Gattermann, K. Hoenicke, F. Ulberth, and E. Anklam. Evaluation of the results from an interlaboratory comparison study of the determination of acrylamide in crispbread and butter cookies. Anal. Bioanal. Chem. 379: 449-457 (2004).
27. G.L. Kennedy Jr. Biological effects of acetamide, formamide, and their mono and dimethyl derivatives: An update. Crit. Rev. Toxicol. 31: 139-222 (2001).
28. L. Koymans, J. H. van Lenthe, R. van de Straat, G. M. Donne-Op den Kelder, and N.P. Vermeulen. A theoretical study on the metabolic activation of paracetamol by cytochrome P-450: indications for a uniform oxidation mechanism. Chem. Res. Toxicol. 2: 60-66 (1989).
29. W.R. Johnson, R.W. Hale, and J.W. Nedlock. Aliphatic amides in cigarette smoke. Tob. Sci. 17: 73 (1973).
30. E. Dybing, W.P. Soderlund, W.P. Gordon, J.A. Holme, G. Christensen, G. Becher, E. Rivedal, and S.S. Thorgeirsson. Studies on the mechanism of acetamide hepatocarcinogenicity. Pharmacol. Toxicol. 60: 9-16 (1987).
31. K. Sakano, S. Oikawa, Y. Hiraku, and S. Kawanishi. Mechanism of metal-mediated DNA damage induced by a metabolite of carcinogenic acetamide. Chem. Biol. Interact. 149: 52-59 (2004).
32. R. Mukund, T.J. Kelly, S.M. Gordon, M.J. Hays, and W.A. McClenny. Status of ambient measurement methods for hazardous air pollutants. Environ. Sci. Technol. 29: 183A-187A (1995).
33. Occupational Safety and Health Administration (OSHA): http://www.osha.gov/dts/chemicalsampling/data/CH_216315.html
34. F. Ramirez, O. Monroy, E. Favela, J.P. Guyot, and F. Cruz. Acetamide degradation by a continous-fed batch culture of Bacillus sphaericus. Appl. Biochem. Biotech. 70-72: 215-223 (1998).
35. B. Lindström, P. Sjöberg, and S. Floberg. Gas chromatographic-mass spectrometric method for the determination of dimethylacetamide in whole blood. J. Chromatogr. 428: 156-159 (1988).
36. C. Gertz and S. Klostermann. Analysis of acrylamide and mechanisms of its formation in deep-fried products. Eur. J. Lipid Sci. Technol. 104: 762-771 (2002).
37. E. Roemer, R, Stabbert, K. Rustemeier, D.J. Veltel, T.J. Meisgen, W. Reininghaus, R.A. Carchman, C.L. Gaworski, and K.F. Podraza. Chemical composition, cytotoxicity, and mutagenicity of smoke from US commercial and reference cigarettes smoked under two sets ofmachine smoking conditions. Toxicology 195: 31-52 (2004).
38. J.N. Diana and A. Vaught. Research Cigarettes. The University of Kentucky Printing Services, Lexington, KY, 1990.
39. H.M. Davies and A. Vaught. The Reference Cigarette. Kentucky Tobacco Research & Development Center, Lexington, KY, 2003.
40. International Standard ISO 3402. In Tobacco and Tobacco Products-Atmosphere for Conditioning and Testing, 3rd ed. International Organization for Standardization, Geneva, Switzerland, 1991.
41. International Standard ISO 3308. International Standard ISO 3308. Cigarettes-Routine Analytical Cigarette Smoking Machine-Definitions and Standard Conditions, 3rd ed. International Organization for Standardization, Geneva, Switzerland, 1991.
42. P.X. Chen and S.C. Moldoveanu. Mainstream smoke chemical analyses for 2R4F Kentucky Reference Cigarette. Beitr. Tabakforsch. 20: 448-458 (2003).
43. I. Schmeltz and D. Hoffmann. Nitrogen-containing compounds in tobacco and tobacco smoke. Chem. Rev. 77: 295-311 (1977).
44. J. C. Leffingwell. Chemical Constitution of Tobacco Leaf and Differences among Tobacco Types. Leffingwell Reports 2001, 1, 1-56. Available at: http://www.leffingwell.com/leffrept.htm
45. F.R. Cassee, J.P. Groten, and V.J. Feron. Changes in the nasal epithelium of rats exposed by inhalation to mixtures of formaldehyde, acetaldehyde, and acrolein. Fundam. Appl. Toxicol. 29: 208-218 (1996).