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A Diels-Alder Reaction Between A Cigarette Mainstream Smoke Component and Benzoquinone

   | 30 dic 2014
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1. Stedman, R. L.: The chemical composition of tobacco and tobacco smoke; Chem. Rev. 68 (1967) 153–207.Search in Google Scholar

2. Baker, R.R.: Smoke chemistry; in: Tobacco Pro-duction, Chemistry and Technology; edited by Davis L.D. and M.T. Nielson, Blackwell Science, Oxford, UK, 1999, pp 398–439.Search in Google Scholar

3. Wooten, J.B., S. Chouchane, and T.E. McGrath: Tobacco smoke constituents affecting oxidative stress, in: Cigarette Smoke and Oxidative Stress, edited by Halliwell B.B. and H.E. Poulsen, Springer, Berlin, 2006, pp 5–46.10.1007/3-540-32232-9_2Search in Google Scholar

4. Halliwell, B.B. and H.E. Poulsen: Cigarette Smoke and Oxidative Stress, Springer, Berlin, 2006 pp 1–100.10.1007/3-540-32232-9Search in Google Scholar

5. Pryor, W.A., D.G. Prier and D.F. Church: Electron-spin resonance study of mainstream and sidestream cigarette smoke: nature of the free radicals in gas-phase smoke and in cigarette tar; Environ. Health Perspect. 47 (1983) pp 345–355.10.1289/ehp.8347345Search in Google Scholar

6. Pryor, W.A. and K. Stone: Oxidants in cigarette smoke; Anal. N.Y. Acad. Sci. 686 (1993) 12–27.10.1111/j.1749-6632.1993.tb39148.xSearch in Google Scholar

7. Maskos, Z., L. Khachatryan, R. Cueto, W.A. Pryor, and B. Dellinger: Radicals from the pyrolysis of tobacco; Energy & Fuels 19 (2005) 791–799.Search in Google Scholar

8. Chouchane, S, J.B. Wooten, F.J. Tewes, A. Wittig, B.P. Muller, D. Veltel, and J. Diekmann: Involvement of semiquinone radicals in the in vitro cytotoxicity of cigarette mainstream smoke; Chem. Res. Toxicol. 19 (2006) 1602–1610.Search in Google Scholar

9. Stohs, S.J., D. Bagchi, and M. Bagchi: Toxicity of trace elements in tobacco smoke; Inhal. Toxicol. 9 (1997) 867–890.Search in Google Scholar

10. Yan, F., S. Williams, G.D. Griffin, R. Jagannathan, S.E. Plunkett, K.H. Shafer, and T. Vo-Dinh: Near-real-time determination of hydrogen peroxide generated from cigarette smoke; J. Environ. Monit. 7 (2005) 681–687.Search in Google Scholar

11. Pethig, R., R.C. Gascoyne, J.A. McLaughlin, and A. Szent-Gyogyi: Ascorbate-quinone interactions: electrochemical, free radical and cytotoxic properties; Proc. Natl. Acad. Sci. USA 80 (1983) 129–132.Search in Google Scholar

12. Leanderson, P. and C. Tagesson: Cigarette smoke-induced DNA-damage: role of hydroquinone and cate-chol in the formation of the oxidative DNA-adduct, 8-hydroxydeoxyguanosine; Chem. Biol. Interact. 75 (1990) 71–81.Search in Google Scholar

13. Seike, K., M. Murata, S. Oikawa, Y. Hiraku, K. Hira-kawa, and S. Kawanishi: Oxidative DNA damage in-duced by benz[a]anthracene metabolites via redox cycles of quinone and unique non-quinone; Chem. Res. Toxicol. 16 (2003) 1470–1476.Search in Google Scholar

14. Li, Y. and M.A. Trush: Oxidation of hydroquinone by copper: chemical mechanism and biological effects; Arch. Biochem. Biophys. 300 (1993) 346–355.Search in Google Scholar

15. Ly, Y. and M.A. Trush: DNA damage resulting from the oxidation of hydroquinone by copper: role for a Cu(II)/Cu(I) redox cycle and reactive oxygen generation; Carcinogenesis 14 (1993) 1303–1311.Search in Google Scholar

16. Roginsky, V.A., L.M. Pisarenko, W. Bors and C. Michel: The kinetics and thermodynamics of quinone-semiquinone-hydroquinone systems under physiolo-gical conditions; J. Chem. Soc., Perkin Trans. 2 (1999) 871–876.Search in Google Scholar

17. Maroz, A. and O. Brede: Reaction of radicals with benzoquinone-addition of electron transfer, Radiat. Phys. Chem. 67 (2003) 275–278.Search in Google Scholar

18. Nicolaou, K.C., S.A. Snyder, T. Montangnon and G. Vassilikogiannakis: The Diels-Alder reaction in total synthesis; Angew. Chem. Int. Ed. 41 (2002) pp 1668–1698.10.1002/1521-3773(20020517)41:10<1668::AID-ANIE1668>3.0.CO;2-ZSearch in Google Scholar

19. Yates, P. and K. Switlak: The 1:1 and 2:1 adducts of cyclopentadiene with p-benzoquinone; Can. J. Chem. 68 (1990) 1894–1900.Search in Google Scholar

20. Rustemeier, K., R. Stabbert, H.-J. Haussmann, E. Roemer, and E.L. Carmines: Evaluation of the poten-tial effects of ingredients added to cigarettes. Part 2: Chemical composition of mainstream smoke, Food Chem. Toxicol. 40 (2002) 93–104.Search in Google Scholar

21. Counts, M. E., F.S. Hsu, and F.J. Tewes: Development of a commercial cigarette “market map” comparison methodology for evaluating new of non-conventional cigarettes; Reg. Toxicol. Pharmacol. (2006) 225–242.Search in Google Scholar

22. Scholtzhauer, W.S. and O.T. Chortyk: Recent Advances in studies on the pyrosynthesis of cigarette smoke constituents, J. Anal. Appl. Pyrolysis 12 (1987) 193–222.Search in Google Scholar

23. Zhuang, S., J.B. Paine, III, T.S. Sherwood, J.A. Fournier, K.B. Koller, Z. Luan, and C.E. Thomas, Jr.: Filters including segmented monolithic sorbent for gas-phase filtration; U.S. Patent number 6814786, November 19, 2004.Search in Google Scholar

24. Bon Aire, A.B. and E.W. Robb, II: Use of Diels-Alder adducts as tobacco additives, U.S. Patent number 3,047,433 July 31, 1962.Search in Google Scholar

25. Johnson, D., B. Quimby and J. Sullivan: An atomic emission detector for gas chromatography; Amer. Lab. October (1995) 1–5.Search in Google Scholar

26. Webster, C. and M. Cooke: Use of an atomic emission detector to study the variation in elemental response for chlorine, carbon, and oxygen in phenols; J. High Resol. Chromatogr. 18 (1995) 319–322.Search in Google Scholar

27. Quimby, B.D. and J.J. Sullivan: Evaluation of a micro-wave cavity, discharge tube, and gas flow system for combined gas chromatography-atomic emission detection; Anal. Chem. 62 (1990) 1027–1034.Search in Google Scholar

28. Sullivan J.J. and B.D. Quimby: Characterization of computerized photodiode array spectrometer for gas chromatograph-atomic emission spectrometry; Anal. Chem. 62 (1990) 1034–1043.Search in Google Scholar

29. Juillet, Y., E. Gilbert, A. Begos, and B. Bellier: Investigation of compound-independent calibration and partial molecular formula determination by gas chromatography-atomic-emission detection for charac-terization of organophosphorus and organosulfur agents related to the chemical weapons convention; Anal. Bioanal. Chem. 383 (2005) 848–856.Search in Google Scholar

30. Quimby, B.D., P.C. Dryden, and J.J. Sullivan: Selective detection of stable-isotope labeled com-pounds using gas chromatography-emission spectro-metry, Synthesis and Applications of Isotopically Labeled Compounds, (1991) 1128–1132.Search in Google Scholar

31. Quimby, B.D., P.A. Larson, and P.C. Dryden: A comparison of the HP G2350 AED versus HP 5921A AED for average values of MDL and selectivity for selected elements; HP Application Note 228-363, 1996.Search in Google Scholar

32. Stevens, N.A., and M.F. Borgerding: Effect of column flow rate and sample injection mode on compound-independent calibration using gas chromatography with atomic emission detection; Anal. Chem. 70 (1998) 4223–4227.Search in Google Scholar

33. Yu, J., L.T. Taylor, S. Aref, J.A. Bodnar, and M.F. Borgerding: Influence of puffing parameters and filter vent blocking condition on nicotine fate in a burning cigarette part 1. Full flavor cigarettes; Beitr. Tabak-forsch. Int. 22 (2006) 185–195.Search in Google Scholar

34. Janak, K., C. Ostman, H. Carlsson, A. Bemgard, and A. Colmsjo: Instrument-induced effects in the analysis of polycyclic aromatic compounds by capillary gas chromatography with atomic emission detection (GC-AED); J. High Resol. Chromatogr. 17 (2004) 135–140.Search in Google Scholar

35. Silverstein, R.M., G.C. Bassler, and T.C. Morrill: Spectrometric Identification of Organic Compounds, John Wiley, New York, 1999, pp. 1–419.Search in Google Scholar

36. Stothers, J.B.: Carbon-13 NMR Spectroscopy, Aca-demic Press, New York, 1972, pp. 1–559.Search in Google Scholar

37. Barsanti, K.C., W. Luo, L.M. Isabelle, J.F. Pankow and D.H. Peyton: Tobacco smoke particulate matter chemistry by NMR; Magn. Reson. Chem. 45 (2006) 167–170.Search in Google Scholar

38. Schonher, H., H.-J. Klimisch and H.-P. Harket: Aging of cigarette smoke concentrate quantitative investigations of artifact formation by gas and particulate phase reactions; Beitr. Tabakforsch. 7 (1973) 18–23.Search in Google Scholar

39. Einolf, W.N., R.N. Ferguson, J.F. Whidby, and J.F. DeBardeleben; Isolation and identification of 2,6-dimethyl and 2,2,6-trimethyl-4-piperidone, artifacts produced by the reaction of cigarette smoke conden-sate and acetone; Beitr. Tabakforsch. 9 (1978) 208–213.Search in Google Scholar

40. U.S. Federal Trade Commission: Cigarettes and related matters. Carbon monoxide, “tar”, and nicotine content of cigarette smoke. Description of new machine and methods to be used in testing; Fed. Register 45 (1980) 46483-46487.Search in Google Scholar

41. Stevenson, C.D., T.D. Halvorsen, and R.C. Reiter: Effect of 13C substitution on the solution electron affinity of p-benzoquinone; J. Am. Chem. Soc. 115 (1993) 12405–12408.Search in Google Scholar

42. Van der Vilet, A.: Oxidative modifications of proteins and lipids by CS; in: Cigarette Smoke and Oxidative Stress, edited by B.B. Halliwell and H.E. Poulsen, Springer-Verlag, Berlin, 2006, pp 47–74.10.1007/3-540-32232-9_3Search in Google Scholar

43. Colby College Web Site; www.colby.edu/chemistry (August 31, 2007).Search in Google Scholar

44. Morrison, R.T. and R.N. Boyd: Organic Chemistry; Second Edition, Allyn and Bacon, Inc., Boston, USA, 1966.Search in Google Scholar

45. Gillner, M., G.S. Moore, H. Cederburg, and K. Gustaf-sson: Environmental Health Criteria 157; World Health Organization, 1994, pp. 1–119.Search in Google Scholar

46. Coleman, W.M.: Personal communication, 2007.Search in Google Scholar

47. Yates, P. and K. Switlak: The 1:1 and 2:1 adducts of cyclopentadiene with p-benzoquinone; Can. J. Chem. 68 (1990) 1984–1990.Search in Google Scholar

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