A 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.

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A neutral fraction of cigarette smoke condensate, which had shown biological activity and was known to contain polynuclear aromatic hydrocarbons (PAH), was fractionated by analytical gel filtration chromatography. These gel fractions were subjected to gas chromatographic separation and their components were identified by relative GC retention times, UV spectra, and mass spectral data. More than 300 PAH, ranging from indene to the dimethylbenzopyrenes, were characterized. This method of isolation has yielded fractions which were more amenable to definitive identifications. The criteria used for identification are tabulated for all the identified PAH compounds.

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The 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.