Pyrolyses of different tobacco leaf varieties, under conditions designed to simulate cigarette smoke formation, demonstrated a correlation between leaf polyphenol levels and pyrolyzate catechol. Bright tobacco varieties contained significantly higher levels of polyphenols as compared to identically cured Burley tobacco varieties and produced correspondingly higher pyrolyzate catechol yields. Leaf constituents, including polyphenols, lignin, cellulose, and sugars, were pyrolyzed to determine potential conversion to catechol and alkylcatechols. Chlorogenic acid, the polyphenol generally present in highest amounts in tobacco leaf, produced the highest pyrolytic conversions to catechol and 4-ethylcatechol. Flavanoids (rutin and quercetin) produced lesser amounts of catechol and 4-alkylcatechols. The polymeric phenolic leaf constituent, lignin, produced significant yields of catechol.Catechol (1,2-dihydroxybenzene), considered an active cocarcinogen (Van Duuren et al., 1973) and the most abundant phenol in cigarette smoke, has been identified (Schlotzhauer et al., 1978;Hecht et al., 1981) as the principal component of the weakly acidic fraction of cigarette smoke condensate which has been shown to possess tumor-promoting activity (Wynder and Hoffmann, 1964;Bock et al., 1969Bock et al., ,1971. A number of compounds, known to be present in tobacco leaf, have been shown to produce catechol under various pyrolytic conditions. Zane and Wender (1963) produced catechol and alkylcatechols by thermal degradation of the leaf tannin, chlorogenic acid, and of the flavanoids, rutin and quercetin, at reported melt temperatures of 600 °C. Caffeic acid, a structural component of chlorogenic acid, was reported (Jones and Schmeltz, 1968) to produce catechol (31.60 mol % yield) by hot tube (700 °C) pyrolysis under nitrogen. Since neither of these studies attempted to closely simulate actual conditions occurring in a burning cigarette, no realistic quantitative relationships between these leaf constituents and smoke catechol levels were determined. Recently, Camella et al. (1980) extracted tobacco leaf with hexane, chloroform, benzene, and methanol and concluded, through pyrolysis studies, that the catechol precursors resided mainly in the methanol extract, which contained chlorogenic acid and sugars. Using a method designed to simulate the formation of cigarette smoke (Schlotzhauer et al., 1979), Schlotzhauer and Chortyk (1981), by pyrolysis