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

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

Contributions to Tobacco & Nicotine Research
Volume 23 (2008): Issue 3 (December 2008)
By:   
Open Access
|Dec 2014
References

References

  1. 1. Stedman, R. L.: The chemical composition of tobacco and tobacco smoke; Chem. Rev. 68 (1967) 153–207.
    Search in Google Scholar
  2. 2. Baker, R.R.: Smoke chemistry;: 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. 3. Wooten, J.B., S. Chouchane, and T.E. McGrath: Tobacco smoke constituents affecting oxidative stress,: Cigarette Smoke and Oxidative Stress, edited by Halliwell B.B. and H.E. Poulsen, Springer, Berlin, 2006, pp 5–46.
    Open DOISearch in Google Scholar
  4. 4. Halliwell, B.B. and H.E. Poulsen: Cigarette Smoke and Oxidative Stress, Springer, Berlin, 2006 pp 1–100.
    Open DOISearch in Google Scholar
  5. 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.
    Open DOISearch in Google Scholar
  6. 6. Pryor, W.A. and K. Stone: Oxidants in cigarette smoke; Anal. N.Y. Acad. Sci. 686 (1993) 12–27.
    Open DOISearch in Google Scholar
  7. 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. 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. 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. 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. 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. 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. 13. Seike, K., M. Murata, S. Oikawa, Y. Hiraku, K. Hira-kawa, and S. Kawanishi: Oxidative DNA damage in-duced by benz[]anthracene metabolites via redox cycles of quinone and unique non-quinone; Chem. Res. Toxicol. 16 (2003) 1470–1476.
    Search in Google Scholar
  14. 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. 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. 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. 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. 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.
    Open DOISearch in Google Scholar
  19. 19. Yates, P. and K. Switlak: The 1:1 and 2:1 adducts of cyclopentadiene with-benzoquinone; Can. J. Chem. 68 (1990) 1894–1900.
    Search in Google Scholar
  20. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 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. 36. Stothers, J.B.: Carbon-13 NMR Spectroscopy, Aca-demic Press, New York, 1972, pp. 1–559.
    Search in Google Scholar
  37. 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. 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. 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. 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. 41. Stevenson, C.D., T.D. Halvorsen, and R.C. Reiter: Effect ofC substitution on the solution electron affinity of-benzoquinone; J. Am. Chem. Soc. 115 (1993) 12405–12408.
    Search in Google Scholar
  42. 42. Van der Vilet, A.: Oxidative modifications of proteins and lipids by CS;: Cigarette Smoke and Oxidative Stress, edited by B.B. Halliwell and H.E. Poulsen, Springer-Verlag, Berlin, 2006, pp 47–74.
    Open DOISearch in Google Scholar
  43. 43. Colby College Web Site; www.colby.edu/chemistry (August 31, 2007).
    Search in Google Scholar
  44. 44. Morrison, R.T. and R.N. Boyd: Organic Chemistry; Second Edition, Allyn and Bacon, Inc., Boston, USA, 1966.
    Search in Google Scholar
  45. 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. 46. Coleman, W.M.: Personal communication, 2007.
    Search in Google Scholar
  47. 47. Yates, P. and K. Switlak: The 1:1 and 2:1 adducts of cyclopentadiene with-benzoquinone; Can. J. Chem. 68 (1990) 1984–1990.
    Search in Google Scholar
DOI: https://doi.org/10.2478/cttr-2013-0855 | Journal eISSN: 2719-9509 (formerly 1612-9237)
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Language: English
Page range: 121 - 136
Submitted on: Oct 11, 2007
Accepted on: Oct 1, 2008
Published on: Dec 30, 2014
Published by: Beiträge zur Tabakforschung GmbH
In partnership with: Paradigm Publishing Services
Related subjects:
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© 2014 WM Coleman, published by Beiträge zur Tabakforschung GmbH
This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Volume 23 (2008): Issue 3 (December 2008)
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