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Corel Office-Dokument Beiträge zur Tabakforschung International/Contributions to Tobacco Research Volume 22 @ No. 1 @ April 2006 The Composition of Cigarette Smoke: A Catalogue of the Polycyclic Aromatic Hydrocarbons* by Alan Rodgman1 and Thomas A. Perfetti2 1 2828 Birchwood Drive, Winston-Salem, North Carolina, 27103-3410, USA 2 Perfetti and Perfetti, LLC, 2116 New Castle Drive, Winston-Salem, North Carolina, 27103-5750, USA SUMMARY letzteren umfassender untersucht als jedes andere Konsum- gut. Fast 4800 Einzelsubstanzen wurden im Tabakrauch Classified as toxicants in many of the substances to which nachgewiesen und unter diesen sind mehr als 500 PAHs humans are exposed are the polycyclic aromatic hydrocar- entweder vollständig oder teilweise identifiziert. Wegen der bons (PAHs). Such exposures include air pollutants from a tumorigenen Wirkung vieler PAHs wurde in vielen Studien variety of sources, foodstuffs and beverages, and tobacco versucht, den Zusammenhang zwischen der Struktur der smoke. Since the early 1950s, the composition of the latter PAHs und ihrer spezifischen tumorigenen Wirkung bei has been more completely defined than that of any other Labortieren zu untersuchen. Durch keine dieser Theorien consumer product. Nearly 4800 components have been lassen sich bis heute alle Fragen vollständig beantworten. identified in tobacco smoke and among these are over 500 Als erster Schritt eines Versuchs, eine schlüssigere Bezie- PAHs either completely or partially identified. Because of hung zwischen der Struktur der PAHs und ihrer tumorige- the tumorigenicity of many PAHs, much research has been nen Wirkung zu entwickeln, wurden die PAHs, die voll- conducted in attempts to define the relationship between ständig oder teilweise im Zigarettenrauch identifiziert sind, the PAH structures and their specific tumorigenicities in katalogisiert. In dieser Systematisierung wird unterschieden laboratory animals. None of the theories to date completely zwischen bicyclischen, tricyclischen, tetracyclischen usw. answers all the questions. PAHs, wobei wiederum jede Gruppe unterteilt ist in As a prelude to an attempt to develop a more reasonable benzenoide und cyclopentanoide-benzenoide PAHs. Eine PAH structure-tumorigenicity relationship, the PAHs andere Einteilung bezieht sich auf diejenigen PAHs, die completely or partially identified in cigarette smoke have Gegenstand mehrerer früherer Studien waren, in denen der been catalogued. In the catalogue, they are categorized as Zusammenhang zwischen Struktur und Tumorigenität, bicyclic, tricyclic, tetracyclic, etc. with each group subdi- hauptsächlich benzenoider PAHs, untersucht wurde. [Beitr. vided into all-benzenoid PAHs and cyclopentanoid-ben- Tabakforsch. Int. 22 (2006) 13–69] zenoid PAHs. Another tabulation includes the PAHs considered in several previous studies on structure-tumori- genicity relationships, studies that dealt primarily with all- RESUME benzenoid PAHs. [Beitr. Tabakforsch. Int. 22 (2006) 13–69] Les hydrocarbures polynucléaires aromatiques (PAHs), contenus dans de nombreuses substances auxquelles l’homme est exposé, sont classifiés comme toxiques. Parmi ZUSAMMENFASSUNG ces expositions comptent les polluants de l’air de sources multiples, l’alimentation, les boissons ou la fumée du tabac. Mit toxisch eingestuften polycyclischen aromatischen Depuis le début des années 1950, la composition chimique Kohlenwasserstoffen (PAHs) sind Menschen vielfach de cette dernière a été analysée de façon plus approfondie exponiert. Die Expositionen umfassen Luftverschmutzung que tout autre produit de consommation. Environ 4800 durch eine Vielzahl von Quellen, Lebensmittel, Getränke substances ont été identifiées dans la fumée du tabac et und Tabakrauch. Seit den frühen fünfziger Jahren des parmi celles-ci plus de 500 PAHs complètement ou partiel- vorigen Jahrhunderts wurde die Zusammensetzung des lement identifiées. Due à la tumorigénicité de nombreux *Received: 21st September 2005 – accepted: 9th January 2006 Unauthenticated Download Date | 10/14/15 5:19 PM PAHs, beaucoup d’études ont été menées en vue d’exa- components and vapor-phase components identified in miner la relation entre les structures des PAHs et leurs tobacco smoke. In his 1968 review, STEDMAN (425) listed tumorigénicités spécifiques chez les animaux de labora- nearly 1200 identified tobacco and smoke components. The toire. Jusqu’à présent aucune de ces théories n’explique next year, NEURATH (256) reported on the presence of 180 complètement toutes les questions. nitrogen-containing compounds in smoke. With the meaning- Une approche dans le but de développer une relation plus ful advancements in analytical methodology, the number of raisonnable entre la structure et la tumorigénicité des tobacco and smoke components increased dramatically (125). PAHs, est la classification des PAHs complètement ou At R. J. Reynolds Tobacco Company (RJRT), SCHUMACHER partiellement identifiés. Dans ce catalogue, les PAHs sont et al. (391), HECKMAN and BEST (147), and NEWELL et al. classifiés comme bicycliques, tricycliques, tetracycliques, (264) identified over 1500 compounds in the water-soluble etc., chaque groupe étant subdivisé en PAHs benzenoid et and ether-soluble fractions of tobacco smoke. In 1977, cyclopentanoid-benzenoid. Un autre catalogue comprend SCHMELTZ and HOFFMANN (381) catalogued nearly 500 N- les PAHs examinés dans des études antérieures sur la containing compounds identified in tobacco smoke but their relation entre la structure et la tumorigénicité, surtout des catalogue did not include the more than 230 N-containing PAHs benzenoid. [Beitr. Tabakforsch. Int. 22 (2006) compounds newly identified in tobacco smoke by HECKMAN 13–69] and BEST (147). Between 1974 and 1978, SNOOK et al. (416, 419–422) published the results of their massive study of the PAHs identified in tobacco smoke, a study that was followed INTRODUCTION by an equally definitive one published in 1981 on the aza- arenes in tobacco smoke (418). In 1980, ISHIGURO and Tobacco and tobacco products in the forms of leaf, shredded SUGAWARA (176) listed 1889 identified tobacco smoke or grounded tobacco, and various forms of cigars and components in their monograph. However, a tally of the cigarettes have been available to individuals for ages. For reported tobacco smoke components at that time exceeded centuries people have enjoyed tobacco but have been 2500. No additional catalogues of the total number of admonished of its potential health concerns. Health concerns identified components of cigarette mainstream smoke (MSS) for cigarette smokers have increased steadily since the early have been published since the 1980 ISHIGURO and SUGA- 1950s due to the rapid development and advancement in WARA (176) publication. SMITH et al. (413) recently reported separation sciences, toxicology and medicine. In his 1954 the chemical structures of the 253 identified phenols reported publication, KOSAK (194) was the first person to catalogue in cigarette MSS. compounds reported in tobacco smoke. His list contained Numerous catalogues of PAHs identified in MSS have been fewer than 100 compounds and a significant number were compiled from 1955 through 2005, including this report. incorrectly characterized. Today nearly 4800 compounds Table 1 is a chronology of catalogues of PAHs in MSS. It have been identified as components in tobacco smoke [see contains the year of each catalogue, author (and reference), Figure 1, p. 140 in (125)]. Over the past fifty years, the and the number of PAHs listed. The previous catalogues Tobacco Industry has made significant progress in both the contain much overlap in terms of the PAHs identified. This identification of tobacco and smoke components and the report attempts to eliminate the overlap and clearly present development of technologies to reduce cigarette smoke the 539 PAHs identified in MSS. Our present report is yields. Significant efforts continue in government, academia, intended to present a referenced catalogue of the either and especially the Tobacco Industry to understand the health completely or partially characterizeda PAHs in tobacco effects of smoking and to develop cigarette products with smoke. The catalogue contains the chemical name, struc- reduced health risks for smokers. One class of tobacco smoke ture, molecular weight, molecular formula, CAS registra- components that has been studied extensively and intensively tion number, and alphabetical listing of references on is the polycyclic aromatic hydrocarbons (PAH) due to their PAHs. potential health concerns. Periodically, tobacco researchers have reported the progress on the identification of tobacco and smoke components. THE IDENTIFICATION OF POLYCYCLIC AROMATIC Review articles by JOHNSTONE and PLIMMER (182) and HYDROCARBONS IN CIGARETTE MAINSTREAM IZAWA (177) detailed the tobacco and smoke research SMOKE conducted over 100 years. IZAWA listed 440 identified smoke components by 1961. QUIN (289) published a review of The significant increase in the number of studies on components found in tobacco and smoke. HERRMANN (151) tobacco smoke composition was triggered by the following reviewed phenolic compounds in tobacco smoke. In 1963, events: a) The results in the early 1950s from several PHILIP MORRIS (278) published a monograph on tobacco and retrospective epidemiology studies (487) in which it was smoke composition, a copy of which was provided the reported that an association existed between cigarette Advisory Committee on smoking and health to the US smoking and the incidence of lung cancer
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