Tobacco components

Yun, et al. Interactions of ingested food, beverage, and tobacco components involving human cytochrome P4501A2, 2A6, 2E1, and 3A4 enzymes. Environ Health Perspect 1994 102(Suppl 9) 49-53. 

Since its characterization in 1956, solanesol has had an interesting history as a tobacco component. It is present ... 

With regard to tobacco components, Lloyd et al. (2389) identified 275 previously unidentified components of additive-free flue-cured tobacco, 132 new to all additive-free tobacco types. Many of these compounds were highly polar and considered significant contributors to MSS flavor and aroma. Similar detailed studies were conducted on the composition of hurley tobacco by Roberts and Rohde (3219), Oriental tobacco by Schumacher and Vestal (3561), and Maryland tobacco by Schumacher (3550). Years later, it became apparent that many of the highly polar components of tobacco and tobacco smoke were identical with similar to many of the components used in the flavor formulations, that is, the top dressing, added to a specific tobacco blend to impart its unique smoking characteristics (1053). Randomly selected publications on the identification of many additive-free tobacco and/or tobacco smoke components are listed in Table II.A-2. 

In addition to his isolation of the alcohol solanesol and contribution to its characterization, Rowland was involved in the isolation and characterization of the hydroxylated flue-cured tobacco components solanachromene and a-tocopherol, each of which is a phenol. The solanachromene has not been identified in tobacco smoke but a-tocopherol, a well-known anticarcinogen, was identified as a cigarette MSS component in 1959 (3271) and many times since in MSS and ETS, for example, see Risner (3170). 

In their 1962-1963 study of hydroxylated tobacco components, Rowland and colleagues next isolated several 1,3- and... 

Table II.B-1 chronicles many of the reported studies on phytosterols and their derivatives in tobacco and tobacco smoke plus the studies on the pyrolysis of phytosterols. Table II.B-2 lists the 111 phytosterols and phytosteryl derivatives identified in tobacco and tobacco smoke. Of these 111 components, 44 have been reported as tobacco smoke components, 102 as tobacco components, and 35 in both tobacco and tobacco smoke.

At R.J. Reynolds Tobacco Co. (RJRT) R D, two anhydrides, 3,4-diethyldihydro-2,4-furandione (diethylsucccinic anhydride) and 3,4-dimethyldihydro-2,4-furandione (dim-ethylsucccinic anhydride) were identified by Jones and Latimer during their research on Oriental tobacco composition. The two anhydrides were listed in their 1943 report on the Oriental tobacco components they identified through the end of 1942 (1980). 

Table VIII-3 lists the carbohydrates and their derivatives identified to date in tobacco, tobacco smoke, and tobacco substitute smoke. Of the 279 identified carbohydrates listed, most of them are tobacco components 271 have been identified in tobacco vs. only 35 in smoke 27 have been identified in both tobacco and smoke.

Van Duuren et al. also noted that rutin, a tobacco component, also inhibited B[a]P carcinogenesis in the mouse skin-painting bioassay. From the results of their biological experiments on cocarcinogenesis (simultaneous and repeated application of an agent, in this case 1,2-benzenediol [catechol]), with B[fl]P, Van Duuren et al. (4029) deduced that 1,2-benzenediol (catechol) showed remarkable cocarcinogenic activity with B[fl]P. They reported ... 

Zane and Wender (4403) described their pyrolysis (pyrolysis temperature that of a Bunsen burner flame) of the tobacco components rutin, quercitin, and chlorogenic acid. In addition to nonphenolic compounds, each pyrolysate was reported to contain 1,2-benzenediol (catechol) with lesser amounts of... 

The amounts of phenol and 4-methylphenol (p-cresol) in the pyrolysates obtained under various conditions from several major tobacco components (cellulose, pectin, and lignin), a tobacco additive (invert sugar), several individual tobacco types (flue-cured tobacco, cased burley tobacco, Maryland tobacco), and a tobacco substitute (spinach) were reported by Rodgman and Mims (3305) and Rodgman and Cook (3286). Table IX.A-14 summarizes the results. 

Spears et al. (3767) and Bell et al. (248) determined the generation of phenol when flue-cured and burley tobaccos and various tobacco components (glucose, sucrose, starch, cellulose, and pectin) were pyrolyzed at various temperatures in an air or nitrogen atmosphere. In each instance, phenol was generated. 

Pyrolysis of Tobacco, Tobacco Components, and Spinach Pbenol Content of Pyrolysate... 

In a continnation of their stndy of the conversion of various tobacco components to catechol, Schlotzhauer et al. (3462) examined the phenols formed dnring the pyrolysis of a variety of tobacco components, inclnding chlorogenic and caffeic acids, rntin and qnercetin, cellulose and lignin, and fructose and sncrose (Table lX.A-15). They reported that chlorogenic acid, nsually the most abundant polyphenol in tobacco, produced the highest levels of 1,2-benzenediol (catechol) and... 

The major components of the aqueous methanol extract were identified as fructose, glucose, sucrose, and chlorogenic acid. Contributions of each of these tobacco components plus the contributions of the tobacco components cellulose and rutin to the 1,2-benzenediol (catechol) level in cigarette MSS were determined in a spiking experiment in which cigarettes were spiked with each of the components mentioned, two of which were radiolabeled (fructose and cellulose). The... 

The most effective additives in PAHs reduction were the nitrates. The following explanation of their effectiveness was offered. When heated, the nitrates generate nitric oxide (NO), an odd-electron componnd, capable of scavenging free radicals thermally generated from tobacco components... 

While Tso (3973) in his 1990 book listed numerous nicotine alkaloid-related amines as identified tobacco components, his list also included ammonia but very few alkylamines and no aromatic aniline-related amines in tobacco [see Table 27-1, Partly in (3973)]. 

In his 1954 compilation of smoke components, Kosak (2170) listed no amide identified to that date. In their 1959 review of tobacco and tobacco smoke components, Johnstone and Plimmer (1971) described the identification of asparagine and glutamine in tobacco and glutamine and nicotinamide in tobacco smoke. The latter were identified in smoke by Buyske et al. (562). In its 1963 monograph on tobacco and smoke components, Philip Morris (2939) listed the amides, asparagine, glutamine, citrulline, and nicotinamide, as tobacco components but only glutamine and nicotinamide as smoke components. 

Adams et al. (23) reported the results of their study on the transfer of 4-(A-methylnitrosamino)-l-(3-pyridinyl)-l-butanone (NNK) from tobacco to MSS and its formation from tobacco components during the tobacco smoking process. 

Table XV-5 lists several NNAs reported as tobacco components that are seldom discussed. To date, none of them has been identified in tobacco smoke.

Table XVII.E-7 summarizes the variation in the structures of the aza-arene compounds identified in tobacco and/ or tobacco smoke. Of particular interest with regard to the 294 aza-arenes cataloged in Table XVII.E-6 is that only twenty-three of the 294 have been identified as tobacco components. Of the twenty-three, just fifteen have been identified in both tobacco and smoke. The number of aza-arenes identified in smoke is 286. Those isolated from or identified in tobacco in greater than trace amounts include l//-indole, 2,3-dihydro-l//-indole, 9//-pyrido[3,4-/ ]indole (norharman), l-methyl-9//-pyrido[3,4-/ ]indole (harman), l//-purine, and quinoline.

Tobacco leaf protein by itself contributes little to smoking quality, but it is a major precursor of hundreds of tobacco smoke components, for example, numerous nitrogenous compounds and amino acids. Similarly, other major tobacco components such as the carbohydrates, carboxylic acids, pigments, polyphenols, fatty compounds, phytosterols, and many primary or secondary compounds play a significant role in producing a myriad of tobacco smoke compounds (3972, 3973, 3974c). 

Many of the ingredients added to cigarettes are identical or essentially similar in composition to natural leaf tobacco components. 

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