The Composition of Cigarette Smoke. An Historical Perspective of Several Polycyclic Aromatic Hydrocarbons

Abstract

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.

The systemic and gonadal toxicity of 3-methylcholanthrene is prevented by daily administration of α-naphthoflavone

“…Early research argued that the highly potent tumorigen 3-methylcholanthrene (3MC) is generated from cholesterol by pyrolysis of phytosterols during different cooking processes and other incomplete combustion processes (Fieser and Fieser, 1949;Kröller, 1964;Rodgman and Perfetti, 2013). Although 3MC may be prepared by a series of chemical reactions from a sterol-derived compound structurally related to cholesterol, it is considered that tobacco smoke, as other combustion processes, contains numerous PAHs, including 3MC, because of pyrolysis of the organic material (Rodgman and Cook, 2009;Pleil et al, 2010). Most of these compounds can cause different toxic responses in different systems by activating the aryl hydrocarbon receptor (AhR), although some seem to act by different pathways (Fujii-Kuriyama and Mimura, 2005).…”

Smoke Chemistry

“…They originate from tobacco waxes either structurally intact or fragmented. Monocyclic and polynuclear aromatic hydrocarbons are generated by the pyrolysis of amino acids, fatty acids, sugars and paraffi ns [31,32] . The formation of hydrocarbons depends on the temperature during the pyrolysis of tobacco.…”