scholarly journals The ldentification of High Molecular Weight Polynuclear Aromatic Hydrocarbons in a Biologically Active Fraction of Cigarette Smoke Condensate

Author(s):  
M.E. Snook ◽  
R.F. Severson ◽  
R.F. Arrendale ◽  
H.C. Higman ◽  
O.T. Chortyk

AbstractA gel filtration chromatography method was developed for the isolation and concentration of the high molecular weight polynuclear aromatic hydrocarbons (PAH) contained in the most biologically active fraction of cigarette smoke condensate (CSC). The unusually complex mixture of large PAH found in CSC necessitated the use of preparative gas chromatography followed by high-pressure liquid chromatography to achieve separation and identification. Mass spectral, ultra-violet absorption, and chromatographic retention data were needed for the comprehensive identification of the large molecular weight PAH components of CSC. The majority of the more than 200 isolated compounds were identified. Compounds newly identified in CSC included 3,4-dimethylenepyrene, 3,4-trimethylenepyrene, cyclopenta(c,-d)pyrene, 4,5-methylenetriphenylene, benzo[b]perylene, and several dibenzofluoranthenes.

Author(s):  
R. F. Severson ◽  
W. S. Schlotzhauer ◽  
R. F. Arrendale ◽  
M. E. Snook ◽  
H. C. Higman

AbstractTobacco, its petroleum ether (PE) extract, and the residual extracted tobacco (marc) were pyrolyzed at 650-750°C, 650-850°C, and 700°C, respectively. Analyses of the polynuclear aromatic hydrocarbons (PAH) produced showed that the pyrolysis of the tobacco and the PE extract at 700°C produced PAH profiles comparable to those found in cigarette smoke condensate (CSC). The data indicated that most of the alkyl PAH and the major PAH in cigarette smoke are derived from the PE extractables of tobacco. The constituents of the marc were the major precursors for phenols, oxygenated PAH, and Iow molecular weight acids; and those of PE extract were the major producers of high molecular weight acids.


Author(s):  
M. E. Snook ◽  
R. F. Severson ◽  
R. F. Arrendale ◽  
H. C. Higman ◽  
O. T. Chortyk

AbstractThe methyl, multi-methyl, and ethyl derivatives of the polynuclear aromatic hydrocarbons (PAH) of cigarette smoke condensate (CSC) were isolated from the neutrals by silicic acid chromatography, solvent partitioning and gel chromatography. The procedure yielded a relatively pure PAH isolate amenable to further identifications. The multi-alkylated PAH were concentrated in the early gel fractions with parent and higher ring PAH found in subsequent gel fractions. It was shown that CSC is very rich in alkylated PAH, and their successful identification required extensive use of gas and liquid chromatography and ultra-violet and GC - mass spectrometric techniques. High-pressure liquid chromatography (HPLC) separated individual isomers of the alkylated PAH in complex GC peaks. PAH from indene to pentamethylchrysene were found. This report concludes our identification studies on the PAH of CSC and complements our two previous reports in this journal. Collectively, our studies have identified approximately 1000 PAH of cigarette smoke condensate and have led to the development of methods for the routine quantitation of PAH in smalI quantities of cigarette smoke condensate.


Author(s):  
W. J. Chamberlain ◽  
D. B. Waiters ◽  
M. E. Snook ◽  
O. T. Chortyk ◽  
F. J. Akin

AbstractCigarette smoke condensate (CSC) was fractionated for bioassay to determine possible tumorigenic activity on mouse skin. Two fractions which previously had shown activity were further separated. A weak-acid fraction (F 8) was separated into three subfractions. A polynuclear aromatic hydrocarboncontaining fraction (F 20) was divided into two fractions by gel permeation chromatography. The polynuclear aromatic hydrocarbons, the suspected active materials in F 20, were successfully concentrated into a fraction (F 55) representing only 0.05 % of CSC. These materials are currently undergoing bioassay.


Author(s):  
R. F. Severson ◽  
M. E. Snook ◽  
O. T. Chortyk ◽  
R. F. Arrendale

AbstractA four-step method has been described for the quantitative analysis of polynuclear aromatic hydrocarbons (PAH) in smoke condensate from 90 or more cigarettes. It involves the extraction of condensate solution with water, silicic acid and gel filtration chromatography, then separation and quantitation by gas chromatography. Individual PAH or totaI PAH profiles of condensates from different cigarettes can now be compared. The method was applied to reference, commercial nonfilter, and commercial filter cigarettes. The details and advantages of the method are elaborated.


Author(s):  
W. S. Schlotzhauer ◽  
O. T. Chortyk

AbstractPyrolytic products of commercial tobacco sheet, flue-cured tobacco leaf, and stems were compared. The yields of acids, bases, neutrals, and phenolics were determined. The neutrals were further characterized by chromatography in order to examine pyrolysis fractions corresponding to biologically active cigarette smoke fractions. Individual phenols, carboxylic acids, polynuclear aromatic hydrocarbons (PAH), and nicotine were determined for sheet and leaf pyrolyzate. Analyses of constituents of various pyrolyzate fractions indicated significantly lower amounts of phenols, PAH, and nicotine in sheet and stem pyrolyzates than in leaf pyrolyzates


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