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.

scholarly journals Comparison of Pyrolytic Products from Flue-Cured Tobacco Leaf and a Reconstituted Tobacco Sheet

1975 ◽  
Vol 8 (2) ◽  
Author(s):  
W. S. Schlotzhauer ◽  
O. T. Chortyk
Keyword(s):  
Carboxylic Acids ◽  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Biologically Active ◽  
Tobacco Leaf ◽  
Reconstituted Tobacco Sheet ◽  
Pyrolytic Products

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

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.

Identification of Polynuclear Aromatic Hydrocarbons in Cigarette Smoke and Their Importance as Tumorigens 2

1976 ◽  
Vol 57 (1) ◽  
pp. 191-195 ◽  
Author(s):  
F. J. Akin ◽  
M. E. Snook ◽  
R. E. Severson ◽  
W. J. Chamberlain ◽  
D. B. Walters
Keyword(s):  
Cigarette Smoke ◽  
Aromatic Hydrocarbons ◽  
Polynuclear Aromatic Hydrocarbons

scholarly journals A three-armed cryptand with triazine and pyridine units: synthesis, structure and complexation with polycyclic aromatic compounds

2018 ◽  
Vol 14 ◽  
pp. 1370-1377 ◽  
Author(s):  
Claudia Lar ◽  
Adrian Woiczechowski-Pop ◽  
Attila Bende ◽  
Ioana Georgeta Grosu ◽  
Natalia Miklášová ◽  
...  
Keyword(s):  
Structural Analysis ◽  
Aromatic Hydrocarbons ◽  
Molecular Modelling ◽  
Aromatic Compounds ◽  
Substitution Reaction ◽  
Polycyclic Aromatic Compounds ◽  
Polynuclear Aromatic Hydrocarbons ◽  
Aromatic Nucleophilic Substitution ◽  
Polycyclic Aromatic ◽  
Aromatic Nucleophilic Substitution Reaction

The aromatic nucleophilic substitution reaction based synthesis of a three-armed cryptand displaying 2,4,6-triphenyl-1,3,5-triazine units as caps and pyridine rings in the bridges, along with NMR, MS and molecular modelling-based structural analysis of this compound are reported. Appropriate NMR and molecular modelling investigations proved the formation of 1:1 host–guest assemblies between the investigated cryptand and some polynuclear aromatic hydrocarbons or their derivatives.

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