Multi-alkylated Polynuclear Aromatic Hydrocarbons of Tobacco Smoke: Separation and Identification

1978 ◽  
Vol 9 (4) ◽  
Author(s):  
M. E. Snook ◽  
R. F. Severson ◽  
R. F. Arrendale ◽  
H. C. Higman ◽  
O. T. Chortyk
Keyword(s):  
Liquid Chromatography ◽  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Ultra Violet ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Gel Chromatography ◽  
Cigarette Smoke Condensate ◽  
Gas And Liquid Chromatography ◽  
Silicic Acid Chromatography ◽  
Derivatives Of

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.

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

1977 ◽  
Vol 9 (2) ◽  
Author(s):  
M.E. Snook ◽  
R.F. Severson ◽  
R.F. Arrendale ◽  
H.C. Higman ◽  
O.T. Chortyk
Keyword(s):  
Molecular Weight ◽  
High Molecular Weight ◽  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Biologically Active ◽  
Retention Data ◽  
Active Fraction ◽  
Cigarette Smoke Condensate ◽  
Preparative Gas Chromatography

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.

scholarly journals Correlation of Polynuclear Aromatic Hydrocarbon Formation Between Pyrolysis and Smoking

1977 ◽  
Vol 9 (1) ◽  
Author(s):  
R. F. Severson ◽  
W. S. Schlotzhauer ◽  
R. F. Arrendale ◽  
M. E. Snook ◽  
H. C. Higman
Keyword(s):  
Molecular Weight ◽  
Aromatic Hydrocarbon ◽  
Petroleum Ether ◽  
High Molecular Weight ◽  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Polynuclear Aromatic Hydrocarbon ◽  
Cigarette Smoke Condensate ◽  
Hydrocarbon Formation

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.

scholarly journals Fractionation of Cigarette Smoke Condensate for Biological Testing: Concentration of Polynuclear Aromatic Hydrocarbon and Weak-Acid Fractions

1975 ◽  
Vol 8 (3) ◽  
Author(s):  
W. J. Chamberlain ◽  
D. B. Waiters ◽  
M. E. Snook ◽  
O. T. Chortyk ◽  
F. J. Akin
Keyword(s):  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Mouse Skin ◽  
Gel Permeation Chromatography ◽  
Weak Acid ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Cigarette Smoke Condensate ◽  
Active Materials ◽  
Gel Permeation ◽  
Tumorigenic Activity

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.

scholarly journals Isolation and ldentification of Aza-Arenes of Tobacco Smoke

1981 ◽  
Vol 11 (2) ◽  
Author(s):  
M. E. Snook ◽  
P. J. Fortson ◽  
O. T. Chortyk
Keyword(s):  
Tobacco Smoke ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Gel Chromatography ◽  
Cigarette Smoke Condensate ◽  
Aliphatic Compounds ◽  
Ring Number ◽  
Silicic Acid Chromatography ◽  
Probable Presence ◽  
First Time ◽  
Aza Arenes

AbstractThe nitrogen analogues of polynuclear aromatic hydrocarbons (aza-arenes) were isolated and identified in a basic fraction of cigarette smoke condensate. Silicic acid chromatography removed the predominant nicotine alkaloids, while gel chromatography on Bio-Beads S-X12 in benzene effectively separated the aza-arenes from interfering aliphatic compounds. In addition, the gel columns separated the aza-arenes by ring number and degree of alkylation on the basis of an adsorption-type mechanism. These gel characteristics facilitated the identifications of a large number of isomeric aza-arenes. Compounds identified included 2-vinylpyridine, 3-vinylpyridine and 2-phenylpyridine as well as quinoline, isoquinoline, 4-azafluorene, benzoquinolines, benzoisoquinolines, 1-azafluoranthene, 7-azafluoranthene, 4-aza-pyrene, 7- azaindole, pyrroloquinoline and their mono-, di- and trimethyl derivatives. All eight possible isomers of benzoquinoline and benzoisoquinoline were found, four of which are being reported for the first time. Evidence was also found for the probable presence of 5,6-benzo-7-azaindole.

A Chromatographic Analysis for Polynuclear Aromatic Hydrocarbons in Small Quantities of Cigarette Smoke Condensate

1976 ◽  
Vol 8 (5) ◽  
Author(s):  
R. F. Severson ◽  
M. E. Snook ◽  
O. T. Chortyk ◽  
R. F. Arrendale
Keyword(s):  
Gas Chromatography ◽  
Quantitative Analysis ◽  
Cigarette Smoke ◽  
Silicic Acid ◽  
Aromatic Hydrocarbons ◽  
Chromatographic Analysis ◽  
Gel Filtration ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Cigarette Smoke Condensate ◽  
Step Method

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.

scholarly journals Pyrogenesis of Aromatic Hydrocarbons Present in Cigarette Smoke II: Pyrolytic Products of some Representative Constituents of the Hexane Soluble Fraction of Tobacco

1969 ◽  
Vol 5 (1) ◽  
pp. 5-8 ◽  
Author(s):  
W. S. Schlotzhauer ◽  
I. Schmeltz
Keyword(s):  
Stearic Acid ◽  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Aromatic Compounds ◽  
Plant Sterol ◽  
Soluble Fraction ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Straight Chain ◽  
Alkyl Side Chains ◽  
Pyrolytic Products

Abstract In continued studies to reevaluate the contribution of the hexane-soluble fraction of flue-cured tobacco to the formation of aromatic compounds, especially polynuclear aromatic hydrocarbons, present in cigarette smoke, some compounds representative of that fraction have been pyrolyzed (860°C, N2). The straight chain saturated compounds, n-hexane, stearic acid, and dotriacontane, produced pyrolysates distinguished by relatively low yields of total neutrals and the absence of any significant quantities of aromatic products with alkyl side chains. Compounds containing double bonds, such as the unsaturated fatty acid, linolenic acid and its methyl ester, and the polyene squalene, which like phytol is also characterized by methyl groups on the chain, produced relatively higher yields of neutral products, including alkyl-substituted aromatic hydrocarbons. Phytol, of course, also exhibited this tendency. Pyrolysis of the plant sterol, b-sitosterol, produced the greatest amounts of phenanthrene and BaP. Estimates of BaP levels in pyrolysates indicate that phytol, in addition to the above mentioned sterol, is a relatively effective high temperature precursor of this important carcinogen. The hexane solubles of flue-cured tobacco were shown to produce BaP in levels intermediate to the least effective (stearic acid) and most effective (b-sitosterol) precursor examined.

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