Tobacco volatiles

The Tenax containing the tobacco volatiles was placed on a CDS 320 Concentrator equipped with a thermal desorber to accept the 6 X 1/2 probe. A liquid nitrogen cryogenic trap was controlled by the LAS for further focusing. Temperature programming and data acquisitions were performed by the Perkin-Elmer Sigma 1 and the Hewlett-Packard 3354 LAS respectively. 

Correlation of Analytical/Sensory Results. Sensory data was correlated with headspace data of tobacco volatiles by factor analysis (BMDP4M) and canonical correlation BMDP6M. Analytical data included factor scores and discriminant analyses scores sensory data included scores from the two MDS dimensions. Sorted rotated factor loadings of combined sensory/analytical data using factor analysis are shown in Table II. Factor one contained those variables from the analytical and sensory data which related to differences between bright (A), burley (B), and oriental (C) (Figure 10). These included dimension 1 in the... 

Matsukura, M., K.Takahashi, M. Kawamoto, S. Ishiguro, and H. Matsushita Identification of 3-hydroxy-4,5-di-methyl-2-(57/)-furanone (Sotolone) in roasted tobacco volatiles Agr. Biol. Chem. 49 (1985) 3335-3337. Matsumoto, T., G. Sakata, Y. Tachibana, and K. Fukui Stereochemistry of nucleophilic addition. fV. Condensation of 2,2,6-trimethylcyclohexanone with tert-butyl acetate in the presence of lithium amide Bull. Chem. Soc. Japan 45 (1972) 1147-1152. 

Aromatic Hydrocarbons. These are the most toxic of the hydrocarbons and inhalation of the vapor can cause acute intoxication. Benzene is particularly toxic and long-term exposure can cause anemia and leukopenia, even with concentrations too low for detection by odor or simple instmments. The currendy acceptable average vapor concentration for benzene is no more than 1 ppm. PolycycHc aromatics are not sufftcientiy volatile to present a threat by inhalation (except from pyrolysis of tobacco), but it is known that certain industrial products, such as coal tar, are rich in polycycHc aromatics and continued exposure of human skin to these products results in cancer. 

N-Nitrosamines are formed during processing and smoking of tobacco products. Proteins, agricultural chemicals and alkaloids in tobacco products serve as major precursors for volatile, nonvolatile, and tobacco-specific nitrosamines (Figure 1). In this review we will summarize the progress achieved in respect to tobacco nitrosamines since the last ACS symposium in Boston in June of 1978 (J ). Additional papers will review the metabolism of cyclic N-nitrosamines, including that of N -nitrosonornicotine 1) and the correlation between tobacco and alcohol consumption and cancer of the upper alimentary tract (J ). 

Nonvolatile Nitrosamines In Tobacco Smoke. Although there are more than 10 million exsmokers in the U.S.A., 53 million adults continue to smoke cigarettes and an additional 10 million still smoke cigars or pipes (39). The cigarette smokers are exposed to about 10 ng of volatile nitrosamines, 20-40 ng of NDELA and, most importantly, to 1-10 pg of tobacco specific N-nitros-amines with each cigarette smoked (Table IV). Similar quantities of the TSNA are found in sidestream smoke. The quantities of TSNA in the smoke are dependent on nitrate, nitrite, tobacco alkaloids and on NNN, NNK and NAT in the tobacco itself (31)>... 

Volatiles and monomers in insoluble polymers. Aroma volatiles from foodstuffs, fruits, spices, tobacco, etc. Residual solvents in pharmaceuticals and printed films. 

Inhalation (IH) The administration of volatile gases and vapours, followed by drug absorption in the lungs or nasal mucosa. Examples include general anaesthetics like nitrous oxide, nicotine from the tar droplets in tobacco smoke, cannabinoids from cannabis leaf smoke and various opiates from burning opium resin. 

Barrefors G, Petersson G. 1993. Assessment of ambient volatile hydrocarbons from tobacco smoke and from vehicle emissions. J Chromatogr 643 71-76. 

Tobacco smoke and iV-nitrosation are the focus of intense research activity. Workers in the field use the following concepts Tobacco-specific /V-nitrosamines (TSNA) mainstream tobacco smoke (MSTS), smoke inhaled in a puff sidestream tobacco smoke (SSTS), smoke evolved by smoldering cigarettes between puffs nitroso organic compounds (NOC), referring especially to IV-nitrosamines volatile NOC (VNOC) and iV-nitroso amino acids (NAA). 

The acid-base chemistry of nicotine is now well known and investigations have shown that nicotine in tobacco smoke or in smokeless tobacco prodncts can exist in pH-dependent protonated or nnprotonated free-base forms. In tobacco smoke, only the free-base form can volatilize readily from the smoke particnlate matter to the gas phase, with rapid deposition in the respiratory tract. Using volatility-based analytical measurements, the fraction of nicotine present as the free-base form can be quantitatively determined. For smokeless tobacco products, the situation differs because the tobacco is placed directly in the oral cavity. Hence, the pH of smokeless tobacco prodncts can be measured directly to yield information on the fraction of nicotine available in the nnprotonated free-base form. It is important to characterize the fraction of total nicotine in its conjugate acid-base states as this dramatically affects nicotine bioavailability, because the protonated form is hydrophilic while the nnprotonated free-base form is lipophilic and thus readily diffuses across membranes (Armitage and Turner 1970 Schievelbein et al. 1973). As drug delivery rate and addiction potential are linked (Henningfield and Keenan 1993), increases in delivery rate due to increased free-base levels affect the addiction potential. 

Nicotine aa> values in tobacco smoke particulate matter can be estimated based on nicotine volatility from the smoke particulate matter phase, as controlled by the gas/partitioning constant Kp (Pankow et al. 1997) ... 

Multiple publications (Pankow et al. 1997 Ingebrethsen et al. 2001 Pankow et al. 2003 Watson et al. 2004) have discussed measuring free-base nicotine directly, addressed the importance of free-base nicotine delivery, and examined the chemical properties of nicotine in cigarette smoke as an important determinant of the effective delivery and bioavailability of nicotine from cigarettes. Pankow et al. (1997) examined how ammonia influences nicotine delivery in tobacco smoke and concluded that conversion of nicotine to the free-base form could be facilitated by ammonia. Based on a theoretical treatment, Pankow et al. (1997) concluded that, under certain circumstances, up to 40% of the nicotine could be available as the volatile free-base form. These authors also concluded that the rate of volatilization was more rapid than that previously measured by Lewis et al. (1995) using denuder technology to examine the properties of mainstream cigarette smoke. 

Pankow JF, Mader BT, Isabelle LM, Luo W, PavUck A, Liang C (1997) Conversion of nicotine in tobacco smoke to its volatile and available unprotonated form through the action of gaseous ammonia. Environ Sci Technol 31 2428-2433... 

Source Pyridine occurs naturally in potatoes, anabasis, henbane leaves, peppermint (0 to 1 ppb), tea leaves, and tobacco leaves (Duke, 1992). Identified as one of 140 volatile constituents in used soybean oils collected from a processing plant that fried various beef, chicken, and veal products (Takeoka et al., 1996). 

Nicotine is an oily, volatile liquid and is the principal alkaloid found in tobacco Nicotiana tabacum). It can be seen to be a combination of two types of heterocycle, i.e. the aromatic pyridine and the non-aromatic N-methylpyrrolidine. 

Tobacco smoke contains more than 3800 different compounds. About 10% of these constimte the particulate phase, which contains nicotine and tar. The remaining 90% contains volatile substances such as carbon monoxide, carbon dioxide, cyanides, various hydrocarbons, aldehydes, and organic acids. Although all of these substances affect the smoker to some degree, nicotine is generally considered to be the primary substance responsible for the pharmacological responses to smoking (Nielsen et al. 2001). 

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