1. bookVolume 23 (2009): Issue 6 (December 2009)
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The Composition of Cigarette Smoke. An Historical Perspective of Several Polycyclic Aromatic Hydrocarbons

Published Online: 30 Dec 2014
Page range: 384 - 410
Received: 09 Sep 2008
Accepted: 04 May 2009
Journal Details
License
Format
Journal
First Published
23 Oct 2013
Publication timeframe
4 times per year
Languages
English

Because of the significant advancements in fractionation, analytical, and characterization technologies since the early 1960s, hundreds of components of complex mixtures have been accurately characterized without the necessity of actually isolating the individual component. This has been particularly true in the case of the complex mixtures tobacco and tobacco smoke. Herein, an historical account of a mid-1950 situation concerning polycyclic aromatic hydrocarbons (PAHs) in cigarette smoke is presented. While the number of PAHs identified in tobacco smoke has escalated from the initial PAH, azulene, identified in 1947 to almost 100 PAHs identified by late 1963 to more than 500 PAHs identified by the late 1970s, the number of PAHs isolated individually and characterized by several of the so-called classical chemical means (melting point, mixture melting point, derivative preparation and properties) in the mid-1950s and since is relatively few, 14 in all. They were among 44 PAHs identified in cigarette mainstream smoke and included the following PAHs ranging from bicyclic to pentacyclic: Acenaphthylene, 1,2-dihydroacenaphthylene, anthracene, benz[a]anthracene, benzo[a]pyrene, chrysene, dibenz[a, h]anthracene, fluoranthene, 9H-fluorene, naphthalene, 1-methylnaphthalene, 2-methylnaphthalene, phenanthrene, and pyrene. One of them, benzo[a]pyrene, was similarly characterized in another study in 1959 by Hoffmann.

1. Rodgman, A.: The analysis of cigarette smoke condensate. I. The isolation and/or identification of polycyclic aromatic hydrocarbons in Camel cigarette smoke; RDR, 1956, No. 9, September 28, see www.rjrtdocs. com 501008241 -8293.Search in Google Scholar

2. Rodgman, A.: The analysis of cigarette smoke con-densate. IV. 3,4,8,9-Dibenzpyrene in Camel cigarette smoke condensate; RDR, 1957, No. 13, October 7, see www.rjrtdocs. com 501008378 -8386.Search in Google Scholar

3. Rodgman, A. and L. C. Cook: The analysis of cigarette smoke condensate. XIV. Polycyclic aromatic hydro-carbons; RDR, 1960, No. 20, May 26, see www.rjrtdocs. com 501008592 -8660.Search in Google Scholar

4. Rodgman, A.: Studies of polycyclic aromatic hydro-carbons in cigarette mainstream smoke: Identification, tobacco precursors, control of levels: A review; Beitr. Tabakforsch. Int. 19 (2001) 361–379.Search in Google Scholar

5. Lefemine, D. V., E. T. Alvord, and S. Z. Cardon: Identification of 3,4-benzpyrene in cigarette paper smoke and tars; Southeastern Reg. Mtg., Am. Chem. Soc., Birmingham, AL (1954).Search in Google Scholar

6. Cardon, S. Z. and E. T. Alvord: The presence of 3,4-benzpyrene in cigarette smoke; Ann. Mtg., Am. Assoc. Adv. Sci., Atlanta, GA (1955) pp. 1–12.Search in Google Scholar

7. Alvord, E. T. and S. Z. Cardon: Separation and identification of 3,4-benzpyrene in cigarette smoke; 9th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 9, Paper No. 24, 1955, p. 13.Search in Google Scholar

8. Kosak, A. I., J. S. Swinehart, and D. Taber: The com- 11. ponents of cigarette smoke. I. Preliminary studies; J. Nat. Cancer Inst. 17 (1956) 375–390. 12.Search in Google Scholar

9. Fieser, L. F.: Chemical carcinogenesis; Arthur Stolle Festschrift (1957) 489–498. 13.Search in Google Scholar

10. Orris L., B. L. Van Duuren, A. I. Kosak, N. Nelson, and F. L. Schmitt: The carcinogenicity for mouse skin and the aromatic hydrocarbon content of cigarette-smoke 14. condensate; J. Natl. Cancer Inst. 21 (1958) 557–561.Search in Google Scholar

11. Fieser, L. F.: More on smoking and health; Chemistry 1964(3) 18–19.Search in Google Scholar

12. Wynder, E. L. and D. Hoffmann: Experimental tobacco carcinogenesis; Adv. Cancer Res. 8 (1964) 249–453.Search in Google Scholar

13. Wynder, E. L. and D. Hoffmann: Tobacco and tobacco smoke: Studies in experimental carcinogenesis; Academic Press, New York, NY (1967).Search in Google Scholar

14. Wynder, E. L. and D. Hoffmann: The role of higher polycyclic hydrocarbons in tobacco carcinogenesis; Proc. Am. Assoc. Cancer Res. 3 (1) (1959) 74; A study of tobacco carcinogenesis. VII. The role of higher polycyclic hydrocarbons; Cancer 12 (1959) 1079–1086.Search in Google Scholar

15. United States Public Health Service (USPHS): Smoking and health: Report of the Advisory Committee to the Surgeon General of the Public Health Service; PHS Publ. No. 1103 (1964).Search in Google Scholar

16. Philip Morris Inc.: Chemical constituents in tobacco and smoke. A compilation of published information; Philip Morris Inc., Richmond, VA (1963) pp. 1–47.Search in Google Scholar

17. Rodgman, A.: The analysis of cigarette smoke condensate. XXXV. A summary of an eight-year study; RDR, 1964, No. 10, February 12, see www.rjrtdocs. com 501008855 -8928.Search in Google Scholar

18. Elmenhorst, H. and G. Reckzeh: Aromatische Kohlen-wasserstoffe im Tabakrauch [Aromatic hydrocarbons in tobacco smoke]; Beitr. Tabakforsch. 2 (1964) 180–204.Search in Google Scholar

19. Snook, M. E., R. F. Severson, R. F. Arrendale, H. C. Higman, and O. T. Chortyk: High molecular weight polynuclear aromatic hydrocarbons of cigarette smoke; 29th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 29, Paper No. 21, 1975, p. 19; The identification of high molecular weight polynuclear aromatic hydrocarbons in a biologically active fraction of cigarette smoke condensate; Beitr. Tabakforsch. Int. 9 (1977) 79–101; Multi-alkylated polynuclear aromatic hydrocarbons of tobacco smoke: Separation and identification; Beitr. Tabakforsch. Int. 9 (1978) 222–247; Snook, M. E., R. F. Severson, H. C. Higman, R. F. Arrendale, and O. T. Chortyk: Polynuclear aromatic hydrocarbons of tobacco smoke: Isolation and identification; Beitr. Tabakforsch. 8 (1976) 250–272; Snook, M. E., R. F. Severson, H. C. Higman, and O. T. Chortyk: Isolation and identification of polynuclear aromatic hydrocarbons of tobacco smoke; 28th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 28, Paper No. 40, 1974, p. 27.Search in Google Scholar

20. Rodgman, A. and T. A. Perfetti: The composition of cigarette smoke: A catalogue of the polycyclic aromatic hydrocarbons; Beitr. Tabakforsch. Int. 22 (2006) 13–69.Search in Google Scholar

21. Cook, J. W., C. L. Hewitt, and I. Hieger: Coal-tar constituents and cancer; Nature 130 (1932) 926; Isolation of a cancer-producing hydrocarbon from coal tar. II. Isolation of 1,2- and 4,5-benzpyrenes, perylene, and 1,2-benzanthracene; J. Chem. Soc. (1933) 395–398.Search in Google Scholar

22. Orchin, M. and E. O. Woolfolk: Molecular complexes with 2,4,7-trinitrofluorenone; J. Am. Chem. Soc. 68 (1946) 1727-1729; Orchin, M., L. Reggel, and E. O. Woolfolk: Molecular complexes with 2,4,7-trinitrofluorenone. II; J. Am. Chem. Soc. 69 (1947) 1225–1227.Search in Google Scholar

23. Wynder, E. L., E. A. Graham, and A. B. Croninger: Experimental production of carcinoma with cigarette tar; Cancer Res. 13 (1953) 855–864.Search in Google Scholar

24. Bradford, J. A., W. R. Harlan, and H. R. Hanmer: Nature of cigaret smoke: Technic of experimental smoking; Ind. Eng. Chem. 28 (1936) 836–839.Search in Google Scholar

25. Hartwell, J. L.: Survey of compounds which have been tested for carcinogenic activity; United States Public Health Service (USPHS) Publ. No. 149, (1947) Washington, DC; Survey of compounds which have been tested for carcinogenic activity; United States Public Health Service (USPHS) Publ. No. 149, 2nd Edition (1951), Washington, DC; Shubik, P. and J. L. Hartwell: Survey of compounds which have been tested for carcinogenic activity, Suppl. 1; United States Public Health Service (USPHS) Publ. No. 149 (1957) Washington, DC; Suppl. 2; USPHS Publ. No. 149 (1969) Washington, DC.Search in Google Scholar

26. Dipple, A., R. C. Moschel, and C. A. H. Bigger: Polynuclear hydrocarbons. Chapter 2 in Chemical carcinogens, Second edition; edited by C. E. Searle, Am. Chem. Soc. Monograph 182, American Chemical Society, Washington, DC (1984) 41–163.Search in Google Scholar

27. Sander, L. C. and S. A. Wise: Polycyclic aromatic hydrocarbon structure index; National Institute of Standards and Technology Special Publication 922 (1997).Search in Google Scholar

28. Bonnet, J. and S. Neukomm: Résultats actuels des recherches chimiques sur la composition de la fumée du tabac [Current results on the chemical research on the composition of tobacco smoke]; Oncologia 10 (1957) 124–129.Search in Google Scholar

29. Lyons, M. J. and H. Johnston: Chemical analysis of the neutral fraction of cigarettes smoke tar; Brit. J. Cancer 11 (1957) 554–562.Search in Google Scholar

30. Lyons, M. J.: Presence of 1,2,3,4-dibenzpyrene in cigarette smoke; Nature 182 (1958) 178.Search in Google Scholar

31. Wynder, E. L. and G. F Wright: Studies on the identification of carcinogens in cigarette tar; Proc. Am. Assoc. Cancer Res. 2 (2) (1956) 159; A study of tobacco carcinogenesis. I. The primary fractions; Cancer 10 (1957) 255–271.Search in Google Scholar

32. Pyriki, C.: Polycyclische und aliphatische Kohlen-wasserstoffe des Tabakrauches [Polycyclic and aliphatic hydrocarbons in tobacco smoke]; German Chem. Soc., Ann. Mtg., Leipzig DDR (1962); Die Nahrung 7 (1963) 439–448.Search in Google Scholar

33. Lavit-Lamy, D. and N. P. Buu-Hoï: The true nature of “dibenzo[a, l]pyrene” and its known derivatives; Chem. Comm. 4 (1966) 92–94.Search in Google Scholar

34. Rodgman, A. and L. C. Cook: The composition of cigarette smoke. I. Solanesyl acetate; Tob. Sci. 3 (1959) 86–88.Search in Google Scholar

35. Rodgman, A.: The composition of cigarette smoke. III. Phytadienes; J. Org. Chem. 24 (1959) 1916–1924.Search in Google Scholar

36. Rodgman, A., L. C. Cook, and S. S. Mims: The composition of cigarette smoke. V. Solanesenes; 14th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 14, Paper No. 23, 1960, pp. 12-13; J. Org. Chem. 26 (1961) 497–501.Search in Google Scholar

37. Friedel, R. A. and M. Orchin: Ultraviolet spectra of aromatic compounds; John Wiley and Sons, Inc., New York, NY (1961).Search in Google Scholar

38. Hofer, L. J. E. and W. C. Peebles: X-ray diffraction patters of 2,4,7-trinitrofluorenone derivatives of aromatic hydrocarbons; Anal. Chem. 24 (1952) 822–826.Search in Google Scholar

39. Soffer, M. D. and R. A. Stewart: The purification and identification of 1-methylnaphthalene; J. Am. Chem. Soc. 74 (1952) 567–568.Search in Google Scholar

40. Shriner, R. L. and R. C. Fuson: The systematic identification of organic compounds: A laboratory manual; 3rd Edition, John Wiley and Sons, New York, NY (1948) p. 259.Search in Google Scholar

41. Fieser, L. F.: Experiments in organic chemistry; 2nd Edition, D. C. Heath and Co., New York, NY (1941) p. 344.Search in Google Scholar

42. Clar, E.: Aromatische Kohlenwasserstoffe: Polycyclische Systeme [Aromatic hydrocarbons: Polycyclic systems]; Springer-Verlag, Berlin, Germany (1952).Search in Google Scholar

43. Ikeda, S.: Contribution to the study of tobacco smoke; Sci. Papers, Inst. Phys. Chem. Res. (Tokyo) 42 (1947) 80.Search in Google Scholar

44. Roffo, A. E.: Espectrograffe de los derivados obtenidos por destilacion directa de los tabacos y su relacion como agentes carcinogenos [Spectrograph of derivatives obtained by direct distillation of tobaccos and the relation to carcinogenic agents]; Bol. Inst. Med. Exptl. Estud. Cáncer 14 (1937) 311–399, see Chem. Abstr. 32 (1938) 38123; Espectrograffe de los derivados obtenidos por destilacion directa de los tabacos y su relacion como agentes carcinogenos [Spectrograph of derivatives obtained by direct distillation of tobaccos and the relation to carcinogenic agents]; Bol. Inst. Med. Exptl. Estud. Cáncer 17 (1940) 279.Search in Google Scholar

45. Roffo, A. H.: 1,2-Benzopirene: Cancerigeno extraido del alquitran del tabaco [1,2-Benzpyrene: A carcinogen extracted from tobacco tar]; Bol. Inst. Med. Exp. Estud. Cáncer 16 (1939) 1–38; Krebserzeugendes Benzpyren gewonnen aus Tabakteer [Cancer-causing benzpyrene obtained from tobacco tar]; Z. Krebsforsch. 49 (1939) 588–597, see Biol. Abstr. 14 (1939) 16122.Search in Google Scholar

46. Larson, P. S., H. B. Haag, and H. Silvette: Tobacco: Experimental and clinical studies; Williams and Wilkins Company, Baltimore, MD (1961) pp. 422–424.Search in Google Scholar

47. Rodgman, A. and T. A. Perfetti: The chemical compo-nents identified in tobacco and tobacco smoke prior to 1954: A chronology of classical chemistry; Beitr. Tabakforsch. Int. 23 (2009) 277–333.Search in Google Scholar

48. Wynder, E. L. and E. A. Graham: Tobacco smoking as a possible etiologic factor in bronchiogenic carcinoma: A study of 684 cases; J. Am. Med. Assoc. 143 (1950) 329–336; Doll, R. and A. B. Hill: Smoking and car-cinoma of the lung. Preliminary report; Brit. Med. J. 1950 (ii) 739–748; Levin, M. L., H. Goldstein, and P. R. Gerhardt: Cancer and tobacco smoking: A preliminary report; J. Am. Med. Assoc. 143 (1950) 336–338; Mills, C. A. and M. M. Porter: Tobacco smoking habits and cancer of the mouth and respiratory system; Cancer Res. 10 (1950) 539–542; Schrek, R., L. A. Baker, G. P. Ballard, and S. Dolgoff: Tobacco smoking as an etiologic factor in disease; Cancer Res. 10 (1950) 49–58; Doll, R. and A. B. Hill: A study of the aetiology of carcinoma of the lung; Brit. Med. J. 1952(ii) 1271–1286; McConnell, B. B., K. C. T. Gordon, and T. Jones: Occupational and personal factors in the etiology of cancer of the lung; Lancet 1952(ii) 651–656; Koulumies, M.: Smoking and pulmonary carcinoma; Acta Radiol. 39 (1953) 255–260; Lickint, F.: Ätiologie und Prophylaxe des Lungenkrebses. 2. Statistische Voraussetzungen zur Klärung der Tabakrauchätiologie des Lungenkrebses [Etiology and prophylaxis of lung cancer. 2. Statistical assumptions for clarification of the tobacco smoke etiology of lung cancer]; Steinkopf (1953); Sadowsky, D. A., A. G. Gilliam, and J. Corn-field: The statistical association between smoking and carcinoma of the lung; J. Natl. Cancer Inst. 13 (1953) 1237–1258.Search in Google Scholar

49. Snook, M. E., H. C. Higman, R. F. Arrendale, and O. T. Chortyk: Isolation and identification of nitrogen analogs of polynuclear aromatic hydrocarbons; 30th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 30, Paper No. 47, 1976, p. 32; Snook, M. E., P. J. Fortson, L. B. Smith, and O. T. Chortyk: Isolation and identification of aza-arenes of tobacco smoke; 32nd Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 32, Paper No. 46, 1978, p. 25; Snook, M. E., P. J. Fortson, and O. T. Chortyk: Isolation and identification of aza-arenes of tobacco smoke; Beitr. Tabakforsch. Int. 11 (1981) 67–78.Search in Google Scholar

50. Newell, M. P., R. A. Heckman, R. F. Moates, C. R. Green, F. W. Best, and J. N Schumacher: The com-position of the ether-soluble portion of the particulate phase of cigarette smoke; 29th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 29, Paper No. 39, 1975, p. 28; Isolation and identification of new components of the ether-soluble portion of cigarette smoke condensate; Tob. Sci. 22 (1978) 6–11.Search in Google Scholar

51. Schumacher, J. N., C. R. Green, and F. W. Best: The composition of the water-soluble portion of cigarette smoke particulate phase; 29th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 29, Paper No. 38, 1975, p. 27; Schumacher, J. N., C. R. Green, F. W. Best, and M. P. Newell: Smoke com-position. An extensive investigation of the water-soluble portion of cigarette smoke; J. Agr. Food Chem. 25 (1977) 310–320.Search in Google Scholar

52. Heckman, R. A. and F. W. Best: An investigation of the lipophilic bases of cigarette smoke condensate; 32nd Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 32, Paper No. 47, 1978, p. 25; Tob. Sci. 25 (1981) 33–39.Search in Google Scholar

53. Lloyd, R. A. Jr, C. W Miller, D. L. Roberts, J. A. Giles, J. P. Dickerson, N. H. Nelson, C. E. Rix, and P. H. Ayers: Flue-cured tobacco flavor. I. Essence and essential oil components; CORESTA 1974 Symp., Montreux, Switzerland (1974); Tob. Sci. 20 (1976) 40–48.Search in Google Scholar

54. Leffingwell, J. C. and E. D. Alford: Volatile constituents of Perique tobacco; Electronic J. Environ. Agr. Food Chem. 4 (2005) 899–915.Search in Google Scholar

55. Peng, F., L. Sheng, B. Liu, H. Tong, and S. Liu: Comparison of different extraction methods: Steam distillation, simultaneous distillation and extraction and headspace co-distillation, used for the analysis of the volatile components in aged flue-cured tobacco leaves; J. Chromat. A 1040 (2004) 1–17.Search in Google Scholar

56. Kotin, P.: Letter to E. H. Guthrie; Staff Director, 1964 Advisory Committee on Smoking and Health (September 6, 1963).Search in Google Scholar

57. Kotin, P. and H. L. Falk: Atmospheric factors in pathogenesis of lung cancer; Adv. Cancer Res. 7 (1953) 475–514.Search in Google Scholar

58. Bonnet, J. and S. Neukomm: Sur la composition chimique de la fumée du tabac. I. Analyse de la fraction neuter [On the chemical composition of tobacco smoke. I. Analysis of the neutral fraction]; Helv. Chim. Acta 39 (1956) 1724–1733.Search in Google Scholar

59. Gilbert, J. A. S. and A. J. Lindsey: Polycyclic hydrocarbons in cigarette smoke: The amounts held in stubs and ash; Brit. J. Cancer 10 (1956) 642–645.Search in Google Scholar

60. Gilbert, J. A. S. and A. J. Lindsey: Polycyclic hydrocarbons in tobacco smoke: Pipe smoking experiments; Brit. J. Cancer 10 (1956) 646–648.Search in Google Scholar

61. Bonnet, J. and S. Neukomm: Carcinogenic and cocarcinogenic substances in tobacco smoke; Acta Unio Internat. Contra Cancrum 15 (1959) 561–563Search in Google Scholar

62. Bonnet, J. and S. Neukomm: New investigations on carcinogenic substances in tobacco smoke; Oncologia 12 (1959) 80–86.Search in Google Scholar

63. Johnstone, R. A. W. and J. R. Plimmer: The chemical constituents of tobacco and tobacco smoke; Chem. Rev. 59 (1959) 885–936.Search in Google Scholar

64. Pietzsch, A.: Zum Nachweis von cancerogenen Kohlen-wasserstoffen im Tabakrauch [On the detection of car-cinogenic hydrocarbons in tobacco smoke]; Pharmazie (Berlin) 14 (1959) 466–473.Search in Google Scholar

65. Zapior, B., J. Platek, and J. Kaleta: Polycyclic aromatic hydrocarbons in the smoke of domestic Polish cigarette brands; Roczniki Chemii 33 (1959) 243–245.Search in Google Scholar

66. Lyons, M. J.: Comparison of aromatic polycyclic hydrocarbons from gasoline engine and diesel engine exhausts, general atmospheric dust, and cigarette smoke condensate; in: Symposium: Analysis of carcinogenic air pollutants, edited by E. Sawicki and K. Cassel, Natl. Cancer Inst. Monograph 9 (1962) 193–199.Search in Google Scholar

67. Cook, J. W., R. A. W. Johnstone, and P. M. Quan: The composition of cigarette smoke. VIII. Some aromatic hydrocarbon constituents; Israel J. Chem. 1 (1963) 356–364.Search in Google Scholar

68. Cooper, R. L. and A. J. Lindsey: The presence of polynuclear hydrocarbons in cigarette smoke; Chem. and Ind. (London) (1953) 1205.Search in Google Scholar

69. Cooper, R. L. and A. J. Lindsey: The presence of 3,4-benzpyrene and other polycyclic hydrocarbons in the combustion products of cigarette paper; Chem. and Ind. (London) (1954) 1260–1261.Search in Google Scholar

70. Cooper, R. L., A. J. Lindsey, and R. E. Waller: The presence of 3,4-benzpyrene in cigarette smoke; Chem. and Ind. (London) (1954) 1418.Search in Google Scholar

71. Cooper, R. L. and A. J. Lindsey: 3,4-Benzpyrene and other polycyclic hydrocarbons in cigarette smoke; Brit. J. Cancer 9 (1955) 304–309.Search in Google Scholar

72. Lindsey, A. J.: The composition of tobacco smoke. Some minor organic constituents; Analyst 80 (1955) 164.Search in Google Scholar

73. Lyons, M. J.: Tobacco smoke products. Assay for polycyclic hydrocarbons; Brit. Emp. Cancer Camp., Ann. Rpt. 33 (1955) 277–278.Search in Google Scholar

74. Campbell, J. M. and A. J. Lindsey: Polycyclic hydro-carbons extracted from tobacco. The effect upon total quantities found in smoking; Brit. J. Cancer 10 (1956) 649–652.Search in Google Scholar

75. Campbell, J. M. and A. J. Lindsey: Polycyclic hydrocarbons in cigar smoke; Brit. J. Cancer 11 (1957) 192–195.Search in Google Scholar

76. Wynder, E. L. and G. F Wright: A study of tobacco carcinogenesis. I. The primary fractions; Cancer 10 (1957) 255–271.Search in Google Scholar

77. Wynder, E. L., G. F Wright, and J. Lam: A study of tobacco carcinogenesis. V. The role of pyrolysis; Proc. Am. Assoc. Cancer Res. 2(4) (1958) 357–358, Cancer 11 (1958) 1140–1148.Search in Google Scholar

78. Lindsey, A. J.: The composition of cigarette smoke: Studies on stubs and tips; Brit. J. Cancer 13 (1959) 195–199.Search in Google Scholar

79. Alexandrov, K., P. Simova, and I. Savatinova: Potentielle kanzerogene Substanzen in Zigarettenrauch. Befund 3,4-Benzpyren [Potential carcinogenic substances in cigarette smoke. 3,4-Benzpyrene found]; Neoplasma 8 (1961) 575–576.Search in Google Scholar

80. Commins, B. T., R. L. Cooper, and A. J. Lindsey: Polycyclic hydrocarbons in cigarette smoke; Brit. J. Cancer 8 (1954) 296–302.Search in Google Scholar

81. Seelkopf, C.: Über die Isolierung cancerogene Stoffe aus dem Zigarettenteer [On the isolation of cancerogenic substances from cigarette tar]; Z. Lebensm. Untersuch. Forsch. 100 (1955) 218–222.Search in Google Scholar

82. Wright, G. F and E. L. Wynder: Further chemical studies of cigarette smoke condensate; Proc. Am. Assoc. Cancer Res. 2(2) (1956) 159.Search in Google Scholar

83. Ahlmann, J.: Detection of polycyclic aromatic hydro-carbons in cigarette tar; Acta Pathol. Microbiol. Scand. 43 (1958) 379–390.Search in Google Scholar

84. Pietzsch, A.: Zum Nachweis von cancerogenen Kohlen-wasserstoffen im Tabakrauch [On the detection of carcinogenic hydrocarbons in tobacco smoke]; Natur-wissenschaften 45 (1958) 445.Search in Google Scholar

85. Scassellati-Sforzolini, G. and G. Salucci: Prime ricerche sulla presenza di idrocarburi cancerigeni nel fumo delle sigarette Italiane [Initial research on the presence of carcinogenic hydrocarbons in the smoke of Italian cigarettes]; Boll. Soc. Ital. Biol. Sper. 34 (1958) 424–426.Search in Google Scholar

86. Lindsey, A. J.: Tobacco smoke; Brit. Med. J. 1959(ii) 506.Search in Google Scholar

87. Candeli, A., A. J. Lindsey, and K. Persaud: Carta di sigarette al sulfammato di ammonio e idrocarburi can-cerigeni [Cigarette paper containing ammonium sul-famate and carcinogenic hydrocarbons]; Bol. Soc. Ital. Biol. Sper. 36 (1960) 452–454.Search in Google Scholar

88. Cuzin, J. L.: Determination of anthracene, pyrene, and benzo[a]pyrene in condensates of tobacco smoke; SEITA (January, 1960).Search in Google Scholar

89. Mouron, J. C., J. Bonnet, and S. Neukomm: Extraction of tobacco by some organic solvents and consequences on chemical composition of the smoke; Oncologia 13 (1960) 271–278.Search in Google Scholar

90. Wynder, E. L.: Laboratory contributions to the tobacco-cancer problem; Symposium on Chemical and biolo-gical problems related to smoking, Stockholm, Sweden (1960); Acta Med. Scand. Suppl. 369 (1961) 63–101.Search in Google Scholar

91. Sasmoco, S. A.: Improvements in or relating to a process for treating tobacco and tobacco obtained by said process; British Patent No. 885,249 (Cl. 130) (December 30, 1961).Search in Google Scholar

92. Scassellati-Sforzolini, G. and A. Mariani: Benzopirene e di altri idrocarburi policiclici nel fumo delle sigarette “Nationale Esportazione” [Benzopyrene and other polycyclic hydrocarbons in the smoke of “Nationale Esportazione”]; Boll. Soc. Ital. Biol. Sper. 37 (1961) 766–768.Search in Google Scholar

93. Scassellati-Sforzolini, G. and A. Mariani: Ricerca del 3:4-benzopirene e di altri idrocarburi policiclici nel fumo di sigarette Italiane: Contributo allo studio dell'azione cancerigene del fumo di tobacco [Research on 3:4-benzopyrene and other polycyclic hydrocarbons in the smoke of Italian cigarettes: Contribution to the study of the carcinogenic action of tobacco smoke]; Ricerca Sci. Rend. 1(2) (1961) 98–117.Search in Google Scholar

94. Scassellati-Sforzolini, G. and G. Saldi: Ulteriori ricerche sugli idrocarburi policiclici del fumeso di sigarette. (Confronto tra il fumo aspirato e quello raccolto nell'aria ambiente) [Further research on the polycyclic hydrocarbon content of the smoke of cigarettes. (Comparison between the aspirated smoke from cigarettes and that recovered from the ambient air)]; Boll. Soc. Ital. Biol. Sper. 37 (1961) 769–771.Search in Google Scholar

95. Parmele, H. B. and C. O. Jensen: Smoking tobacco product; British Patent No. 903,067 (August 9, 1962).Search in Google Scholar

96. Pietzsch, A.: Ein weiterer Beitrag zum Thema Reti-nierung von Rauchbestandteilen beim Zigaretten-rauchen [An additional contribution to the theme of retention of smoke components from cigarette smoke]; Pharmazie (Berlin) 17 (1962) 36–41.Search in Google Scholar

97. Cuzin, J. L., A. Testa, S. Testa, and G. Anguerra: Chemical and biological control of condensates from smoked tobacco treated after the Neukomm-Bonnet process; Z. Präventivmed. 28 (1963) 125–137.Search in Google Scholar

98. Dickey, J. B. and G. P. Touey: Tobacco research: Hydrocarbon components of the gaseous phase of cigarette smoke; Seminar presented at Research Dept., R. J. Reynolds Tobacco Company, Winston-Salem NC (March 1, 1956), edited by A. Rodgman, see www.rjrtdocs. com 503132566 -2594.Search in Google Scholar

99. Tennessee Eastman Corporation: Composition of tobacco smoke; Tennessee Eastman Corp. Res. Rpt. No. 4-1201-1 (August 21, 1956).Search in Google Scholar

100. Lyons, M. J.: Assay of possible carcinogenic hydro-carbons from cigarette smoke; Nature 177 (1956) 630–631.Search in Google Scholar

101. Kröller, E.: Ergebnisse vergleichender Schwel- und Rauchversuche an Tabak [Comparative results of smoldering and smoking studies on tobacco]; Deut. Lebensm. Rundschau 60 (1964) 214–215.Search in Google Scholar

102. Hoffmann, D. and E. L. Wynder: Identification of poly-nuclear aromatic hydrocarbons; 136th Natl. Mtg., Am. Chem. Soc., Atlantic City, NJ (1959) Paper No. 16U.Search in Google Scholar

103. Wynder, E. L. and D. Hoffmann: A study of tobacco carcinogenesis. VII. The role of higher polycyclic hydrocarbons; Cancer 12 (1959) 1079–1086.Search in Google Scholar

104. Hoffmann, D. and E. L. Wynder: Short-term deter-mination of carcinogenic aromatic hydrocarbons; Anal. Chem. 32 (1960) 295–296.Search in Google Scholar

105. Hoffmann, D. and E. L. Wynder: On the isolation and identification of polycyclic aromatic hydrocarbons; Cancer 13 (1960) 1062–1073.Search in Google Scholar

106. Wynder, E. L. and D. Hoffmann: Present status of laboratory studies on tobacco carcinogenesis; Acta Pathol. Microbiol. Scand. 52 (1961) 119–132.Search in Google Scholar

107. Lettré, H. and A. Jahn: Zur Bildung aromatischer Kohlenwasserstoffe während des Rauchprozesses [The formation of aromatic hydrocarbons during the smoking process]; Naturwissenschaften 42 (1955) 210.Search in Google Scholar

108. Neukomm, S. and J. Bonnet: Untersuchungen über cancerogene Stoffe im Tabakrauch [Investigation of carcinogenic substances in tobacco smoke]; Strahlen-Therapie 37 (Suppl.) (1957) 128–132.Search in Google Scholar

109. Rand, H. J., E. T. Alvord, S. Z. Cardon, and A. Burhan: A study of cigarette smoke and cigarette paper smoke alone; Am. J. Surg. 94 (1957) 438–443.Search in Google Scholar

110. Wynder, E. L. and D. Hoffmann: The role of higher polycyclic hydrocarbons in tobacco carcinogenesis; Proc. Am. Assoc. Cancer Res. 3(1) (1959) 74.Search in Google Scholar

111. Bonnet, J.: What carcinogenic substances have been demonstrated to be present in tobacco smoke conden-sate; Proc. 1st Workshop Conf. on Lung Cancer Res. (App. A) (1958) 27–30.Search in Google Scholar

112. British Empire Cancer Campaign: Aromatic polycyclic hydrocarbons in cigarette smoke; Brit. Emp. Cancer Camp., Ann. Rpt. 35 (1958) 303–305.Search in Google Scholar

113. Bentley, H. R. and E. G. N. Berry: The constituents of tobacco smoke: An annotated bibliography. Research Paper No. 3; Tobacco Manufacturers’ Standing Committee, London (1959).Search in Google Scholar

114. Van Duuren, B. L.: The polynuclear aromatic hydro-carbons in cigarette-smoke condensate. II; J. Natl. Cancer Inst. 21 (1958) 623–630.Search in Google Scholar

115. Van Duuren, B. L. and N. Nelson: The polycyclic aro-matic hydrocarbons in cigarette smoke; Proc. Am. Assoc. Cancer Res. 2(4) (1958) 353.Search in Google Scholar

116. Tennessee Eastman Corporation: Composition of tobacco smoke. II. Composition of tobacco extract and its pyrolysis products; Tennessee Eastman Corp. Res. Rpt. No. 4-1201-2 (April 13, 1959).Search in Google Scholar

117. Mold, J. D., T. B. Walker, and L. G. Veasey: Selective separation of polycyclic aromatic compounds by countercurrent distribution with a solvent system containing tetramethyluric acid; Anal. Chem. 35 (1963) 2071–2074.Search in Google Scholar

118. Neukomm, S.: The newt test in relation to investigations on carcinogenic substances; in: Symposium: Analysis of carcinogenic air pollutants, edited by E. Sawicki and K. Cassels Jr, J. Natl. Cancer Inst. Monograph 9 (1962) 71–73.Search in Google Scholar

119. Gil-Av, E. and J. Shabtai: Precursors of carcinogenic hydrocarbons in tobacco smoke; Nature 197 (1963) 1065–1066.Search in Google Scholar

120. Van Duuren, B. L.: Identification of some polynuclear aromatic hydrocarbons in cigarette-smoke condensate; J. Natl. Cancer Inst. 21 (1958) 1–16.Search in Google Scholar

121. Wieske, R.: Zur Beurteilung von Filterzigaretten [On the evaluation of filter cigarettes]; Z. Lebensm. Untersuch. Forsch. 102 (1955) 123–127.Search in Google Scholar

122. Wright, G. F and E. L. Wynder: Fractionation of cigarette tar; Proc. Am. Assoc. Cancer Res. 2(1) (1955) 55.Search in Google Scholar

123. Alvord, E. T. and S. Z. Cardon: Inhibition of the formation of 3,4-benzpyrene from cigarette paper smoke; Ann. Mtg., Am. Assoc. Adv. Sci., Atlanta GA (1955); The inhibition of the formation of 3,4-benzpyrene in cigarette smoke; Brit. J. Cancer 10 (1956) 498–503.Search in Google Scholar

124. Falk, H. L. and P. Kotin: The experimental production of hydrocarbons in simulated cigarette smoking: Their analysis and quantitation; Progress Report No. 1, December 14, 1955, see http://legacy.library.ucsf.edu/tid/xxt6aa00; Falk, H. L.: The experimental production of hydrocarbons in simulated cigarette smoking: Their analysis and quantitation; Progress Report No. 2, February 1–November 20, 1956, see http://legacy.library.ucsf.edu/tid/uxt6aa00.Search in Google Scholar

125. Babin, J., D. Polic, and B. Neskovic: Detection of carcinogenic substances in wide use. I. The amount of 3,4–benzpyrene in the smoke of “Morava” cigarettes; Glasnik 14 (4) (1956) 45–52.Search in Google Scholar

126. Cardon, S. Z., E. T. Alvord, W. J. Rand, and R. Hitchcock: 3,4-Benzpyrene in the smoke of cigarette paper, tobacco, and cigarettes; Brit. J. Cancer 10 (1956) 485–497.Search in Google Scholar

127. Kuratsune, M.: Benzo[a]pyrene content of certain pyrogenic materials; J. Natl. Cancer Inst. 16 (1956) 1485–1496.Search in Google Scholar

128. Lam, J.: Determination of 3,4-benzopyrene and other aromatic hydrocarbons formed by pyrolysis of aliphatic tobacco hydrocarbons; Acta Path. Microbiol. Scand. 39 (1956) 207–210.Search in Google Scholar

129. Lettré, H., A. Jahn, and C. Hausbeck: Nachweis von 3,4-Benzpyrene unter den Rauchprodukten [Detection of 3,4-benzpyrene in smoke products]; Angew. Chem. 68 (1956) 212–213.Search in Google Scholar

130. Wynder, E. L. and G. F Wright: Studies on the identification of carcinogens in cigarette tar; Proc. Am. Assoc. Cancer Res. 2(2) (1956) 159.Search in Google Scholar

131. Wright, G. F: Studies with tobacco smoke condensate; in: Proc. 3rd Natl. Cancer Conf., June, 1956, JB Lippincott Company (1957) 479–484.Search in Google Scholar

132. Neukomm, S.: Experimental studies on the carcinogenic power of tobacco smoke and other contaminants of the atmosphere; Oncologia 10 (1957) 137–155.Search in Google Scholar

133. Wieske, R.: Untersuchungen über cancerogene Bestandteile im Tabakrauch [Investigations of the carcinogenic components in tobacco smoke]; Arznei-mittelforschung 7 (1957) 324–329.Search in Google Scholar

134. Bentley, H. R. and J. G. Burgan: Benzopyrene in tobacco and tobacco smoke; 12th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 12, Paper No. 16, 1958, pp. 6–7; . Polynuclear hydrocarbons in tobacco and tobacco smoke. I. 3,4-Benzpyrene; Analyst 83 (1958) 442–447.Search in Google Scholar

135. Cardon, S. Z.: 3,4-Benzpyrene in cigarette smoke; Tob. Sci. 2 (1958) 130–131.Search in Google Scholar

136. Clemo, G. R.: Some aspects of the chemistry of tobacco smoke. I; Tetrahedron 3 (1958) 168–174.Search in Google Scholar

137. Cuzin, J. L.: What is evidence for the presence of significant amounts of carcinogens in cigarette paper? In cigarette tobacco? In cigarette additives? Proc. 1st Conf. Lung Cancer Res. (1958) 49–50.Search in Google Scholar

138. Hubert-Habart, M., R. Latarjet, D. Lavalette, B. Muel, L. René, and R. Royer: Comparaison des quantités de benzo-3,4 pyrène formées par combustion de divers types de papiers à cigarettes [Comparison of the quantities of 3,4-benzpyrene formed by the combustion of different types of cigarette papers]; Bull. Cancer 53 (1958) 53–56.Search in Google Scholar

139. Latarjet, R., J. L. Cuzin, M. Hubert-Habart, B. Muel, and R. Royer: Détection quantitative du 3,4 benzo-pyrène formé par combustion du papier à cigarettes et du tabac [Quantitative detection of 3,4-benzpyrene formed by the combustion of cigarette paper and tobacco]; Bull. Assoc. France Étude Cancer 43 (1956) 180–198.Search in Google Scholar

140. Van Duuren, B. L.: The polynuclear hydrocarbons in cigarette smoke condensate; Proc. 1st Workshop Conf. on Lung Cancer Research (1958) 52–55.Search in Google Scholar

141. Burgan, J. G.: The manufacturers’ contribution to experimental research on smoking and lung cancer; Trans. Assoc. Ind. Med. Officers 9 (1959) 13–17.Search in Google Scholar

142. Dikun, P. P.: Use of the fine structure of the fluorescence spectrum of 3:4-benzpyrene to increase the certainty of its detection; Voprosy Onkol. 5 (12) (1959) 672–677.Search in Google Scholar

143. Dikun, P. P. and S. G. Chushkin: Fluorescence spectral analysis of the products of tobacco smoke; Voprosy Onkol. 5(7) (1959) 34–37.Search in Google Scholar

144. Lindsey, A. J., K. Persaud, and A. Candeli: Reduction of benzpyrene in tobacco smoke; Brit. Med. J. 1959(ii) 821.Search in Google Scholar

145. Tennessee Eastman Corporation: Composition of tobacco smoke. III. Effects of the extraction of tobacco on amount of benzo[a]pyrene in cigarette smoke tar; Tennessee Eastman Corp. Res. Rpt. No. 4-1201-3 (July 14, 1959).Search in Google Scholar

146. Wynder, E. L., G. F Wright, and J. Lam: A study of tobacco carcinogenesis. VI. The role of precursors; Cancer 12 (1959) 1073–1078.Search in Google Scholar

147. Bentley, H. R. and J. G. Burgan: Polynuclear hydrocarbons in tobacco and tobacco smoke. II. The origin of 3,4-benzpyrene found in tobacco and tobacco smoke; Analyst 85 (1960) 723–727.Search in Google Scholar

148. Bentley, H. R. and J. G. Burgan: Polynuclear hydrocarbons in tobacco and tobacco smoke. III. The inhibition of the formation of 3,4-benzpyrene in cigarette smoke; Analyst 85 (1960) 727–730.Search in Google Scholar

149. Candeli, A., A. J. Lindsey, and K. Persaud: Determination of polycyclic aromatic hydrocarbons in tobacco smoke; Anal. Chim. Acta 22 (1960) 458–461.Search in Google Scholar

150. Clemo, G. R.: Further aspects of the chemistry of tobacco smoke. II; Tetrahedron 11 (1960) 11–14.Search in Google Scholar

151. Cuzin, J. L., M. Hubert-Habart, B. Muel, R. Roger, and R. Latarjet: La production du benzo-3,4-pyrene dans des cigarettes à papier imprégné de sulfamate d'ammonium [The production of 3,4-benzopyrene in cigarettes with paper impregnated with ammonium sulfamate]; Bull. Soc. Chim. France (1960) 982.Search in Google Scholar

152. Dikun, P. P., S. G. Chushkin, A. L. Gritsiute, and A. L. Mironova: The results of studies on the possible carcinogenic effect of tobacco products; Voprosy Onkol. 6 (1960) 603–604.Search in Google Scholar

153. Hubert-Habart, M. R.: Le benzo-3,4 pyrène pyroformé dans les produits de combustion de la cigarette: Détection, dosage, recherche des facteurs d'inhibition [Pyrogenesis of 3,4-benzpyrene in the products from cigarette combustion: Detection, yield, research on inhibition factors]; Thesis, University of Paris (1960).Search in Google Scholar

154. Pavlu, J. and J. Sula: Detection and estimation of 3,4-benzpyrene and arsenic in cigarette smoke; Casopis Lekaru Ceskych 96 (1960) 101–104, for translation see www.rjrtdocs. com 503288286 -8293.Search in Google Scholar

155. Takayama, S. and K. Oota: Chemical analysis of cigarette tar produced by human smoking; Gann 51 (1960) 97–103.Search in Google Scholar

156. Grimmer, G.: Eine Methode zur Bestimmung von 3,4-Benzpyrene in Tabakrauchkondensaten [A method for the estimation of 3,4-benzpyrene in tobacco smoke condensate]; Beitr. Tabakforsch. 1 (1961) 107–116.Search in Google Scholar

157. Guérin, M.: Étude sur la pouvoir cocarcinogène du goudron de fumée de cigarette [Study of the cocarcinogenic property of tar from cigarette smoke]; Bull. Assoc. Franc. Étude Cancer 48 (1961) 365–376.Search in Google Scholar

158. Mouron, J. C., J. Bonnet, and S. Neukomm: Variations de la composition chimique de la fumée du tabac par l'addition de produites purs à du tabac complètement extrait [Variations in the chemical composition of the smoke from tobacco by addition of pure products to completely extracted tobacco]; Bull. Soc. Vaudoise Sci. Nat. 67 (1961) 447–453.Search in Google Scholar

159. Rand, H. J., S. Z. Cardon, E. T. Alvord, and A. Burhan: A study of cigarette smoke and cigarette paper smoke alone; Cancer Cytol. 4 (1961) 18–21.Search in Google Scholar

160. Barkemeyer, H.: Eine neue Methode zur Bestimmung des 3,4-Benzpyrens in Tabakrauchkondensaten [A new method for the determination of 3,4-benzpyrene in tobacco smoke condensate]; Beitr. Tabakforsch. 1 (1962) 325–328.Search in Google Scholar

161. Bell, J. H.: Determination of benzo[a]pyrene in cigarette smoke condensate; Report, August 30, 1962, see www.Lorillarddocs. com 00118749 -8752.Search in Google Scholar

162. Bentley, H. R.: A study of carcinogenic components in tobacco smoke; Brit. Emp. Cancer Camp., Ann. Rpt. 39 (1962) 25.Search in Google Scholar

163. Dikun, P. P., N. D. Krasnitskaya, and S. G. Chushkin: Some data on the content of 3,4-benzpyrene in tobacco smoke; Voprosy Onkol. 8 (1962) 31–35.Search in Google Scholar

164. Druckrey, H. and A. Schildbach: Quantitativen Unter-suchungen zur Bedeutung des Benzpyrens für die carcinogene Wirkung von Tabakrauch [Quantitative investigation of the significance of benzpyrene in the carcinogenic action of tobacco smoke]; Z. Krebsforsch. 65 (1963) 465–470.Search in Google Scholar

165. Hoffmann, D., G. Rathkamp, and E. L. Wynder: Com-parison of the yields of several selected components in the smoke from different tobacco products; J. Natl. Cancer Inst. 31 (1963) 627–637.Search in Google Scholar

166. Scherbak, M. P., R. L. Rice, and J. E. de Souza: An absolute method for the determination of 3,4-benzpyrene in cigarette smoke; 17th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 17, Paper No. 20, 1963, pp. 15–16.Search in Google Scholar

167. Testa, A., P. Testa, and J. L. Cuzin: A rapid analytical technique for routine determination of benzo[a]pyrene in cigarette smoke condensate; 17th Tobacco Chemists’ Research Conference, Program Booklet and Abstracts, Vol. 17, Paper No. 19, 1963, p. 15.Search in Google Scholar

168. Waltz, P. and M. Häusermann: Sur un traitement du tabac en vue de diminuer la teneur en hydrocarbures policycliques de la fumée [On the treatment of tobacco to diminish the level of polycyclic hydrocarbons in its smoke]; Z. Präventivmed. 8 (1963) 111–124.Search in Google Scholar

169. Izawa, M.: Review of studies of tobacco smoke; Nippon Senbai Kosha (1961).Search in Google Scholar

170. Schoental, R.: Carcinogenic activity of 3,4,9,10-dibenzpyrene; Acta Unio Internat. Contra Cancrum 15 (1959) 216–219.Search in Google Scholar

171. Johnstone, R. A. W. and P. M. Quan: Naphthalenes in cigarette smoke; Nature 199 (1963) 1184.Search in Google Scholar

172. Wynder, E. L.: Statement on the lung cancer-cigarette smoking controversy: Chemical fractionation of cigarette smoke; in: False and misleading advertising (Filter-tip cigarettes), Hearing before Subcommittee of the Committee on Government Operations (the Blatnik Hearings on Filtered Cigarettes), House of Represen-tatives, 85th Congress, 1st Session (1957) 63–114, see p. 104.Search in Google Scholar

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