Roles of tobacco cellulose, sugars, and chlorogenic acid as precursors to catechol in cigarette smoke

Carmella, Steven G.; Hecht, Stephen S.; Tso, T. C.; Hoffmann, Dietrich

doi:10.1021/jf00122a023

Cited by 40 publications

(39 citation statements)

References 6 publications

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“…6. A significant increase in the yield of catechol and phenol was observed when CGA was added to bright tobacco, which is consistent with previous literature results [14,21,27,29,31]. CGA also increased the yield of hydroquinone as recently reported by Dyakonov et al [14] and Torikaiu et al [32].…”

Section: Co-pyrolysis Of Tobacco With Selected Tobacco Componentssupporting

confidence: 91%

“…It has been reported that chlorogenic acid (CGA) is a significant precursor to catechol [3,21,22,27,29,31]. During the curing of burley tobacco, CGA levels decrease due to interactions of CGA with polyphenol oxidase to form CGA-quinone and this in turn can form polymeric pigments by complexing with amino acids [38,40,41].…”

Section: Comparison Of Phenolic Yields From Bright Burley and Orienmentioning

confidence: 99%

“…Schlotzhauer et al [25] reported on the contributions of different solvent extracts to the overall yields of phenol and cresols by pyrolyzing the different extracts at 860 8C. In a similar set of experiments, Carmella et al [31] sequentially extracted tobacco with hexane and methanol/water and pyrolyzed the extracts at 650 8C. The methanol/water extract and the extracted tobacco were both reported to be precursors of catechol.…”

Section: Effect Of Water Extraction On Phenolic Compound Yieldsmentioning

confidence: 99%

“…Despite numerous papers addressing the formation of selected phenolic compounds, there is little information available in the current literature on their temperature of formation. Selected tobacco constituents such as chlorogenic acid, caffeic acid, rutin, quercetin, cellulose, pectin, and lignin have all been previously identified as potential precursors of catechol, phenol, and cresols [14,21,24,27,29,31]. While hydroquinone has been detected in cigarette smoke at levels similar to catechol for reference cigarettes [13], relatively little information is available on the formation and yields of hydroquinone from different tobaccos or selected tobacco components [14,26,32].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Phenolic compound formation from the low temperature pyrolysis of tobacco

McGrath

Brown

Meruva

et al. 2009

Journal of Analytical and Applied Pyrolysis

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Section: Co-pyrolysis Of Tobacco With Selected Tobacco Componentssupporting

confidence: 91%

Section: Comparison Of Phenolic Yields From Bright Burley and Orienmentioning

confidence: 99%

Section: Effect Of Water Extraction On Phenolic Compound Yieldsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phenolic compound formation from the low temperature pyrolysis of tobacco

McGrath

Brown

Meruva

et al. 2009

Journal of Analytical and Applied Pyrolysis

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“…Beside its natural occurrence [32][33][34][35], phenol is a product of the thermal degradation of CAT and HQ [27,36] and is abundantly found in mainstream tobacco smoke [37]. Its pyrolysis, as it can be seen from Figure 2, shows a linear increase trend with all pyrolysis temperatures.…”

Section: Time Dependence Of Total Radical Accumulationmentioning

confidence: 99%

Gas Chromatography Mass Spectrometry Identification of Labile Radicals Formed during Pyrolysis of Catechool, Hydroquinone, and Phenol through Neutral Pyrolysis Product Mass Analysis

Adounkpè

Aïna

Mama

et al. 2013

ISRN Environmental Chemistry

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Catechol, hydroquinone, and phenol are known to be environmental pollutants due to their ability to generate environmentally free radicals, which cause millions of deaths worldwide. Recently, efforts have been done to precisely identify the origin and the nature of those free radicals employing EPR-LTMI technique. All the three precursors generate cyclopentadienyl radical as major pyrolysis products and phenoxyl radical as both pyrolysis and photolysis products which were obtained from phenol; ortho-semiquinone and para-semiquinone were seen, respectively, from the pyrolysis of catechol and hydroquinone. However, it has been suspected that the solely use of the EPR-LTMI did not allow the isolation of the more labile radicals that is supposedly terminated by radicalradical or radical-surface interaction. The present study reports the gas chromatography mass analysis of the pyrolysis products from catechol, hydroquinone, and phenol. Naphthalene , indene, and hydroxyindene were observed as the pyrolysis products of hydroquinone, while fluorene, 1H-indenol and its isomer 1H-inden-1-one 2,3 dihydro, acenaphthylene, benzofuran-7-methyl, and benzofuran-2-methyl were observed as pyrolysis products of catechol. Dibenzo dioxin and dibenzo furan were observed from pyrolysis of catechol and hydroquinone. Those products result from the combination of radicals such as cyclopentadienyl, parasemiquinone, ortho-semiquinone, hydroxyl-cyclohexadienyl, phenoxyl, and most importantly Hydroxycyclopentadienyl which was not identified by EPR-LTMI.

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Lung carcinogenesis by tobacco smoke

Hecht

2012

Intl Journal of Cancer

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389

299

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Cigarette smoke is a complex mixture of chemicals including multiple genotoxic lung carcinogens. The classic mechanisms of carcinogen metabolic activation to DNA adducts, leading to miscoding and mutations in critical growth control genes, applies to this mixture but some aspects are difficult to establish because of the complexity of the exposure. This paper discusses certain features of this mechanism including the role of nicotine and its receptors; lung carcinogens, co-carcinogens and related substances in cigarette smoke; structurally characterized DNA adducts in the lungs of smokers; the mutational consequences of DNA adduct formation in smokers’ lungs; and biomarkers of nicotine and carcinogen uptake as related to lung cancer. While there are still uncertainties which may never be fully resolved, the general mechanisms by which cigarette smoking causes lung cancer are well understood and provide insights relevant to prevention of lung cancer, the number one cancer killer in the world, causing 1.37 million deaths per year.

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Roles of tobacco cellulose, sugars, and chlorogenic acid as precursors to catechol in cigarette smoke

Cited by 40 publications

References 6 publications

Phenolic compound formation from the low temperature pyrolysis of tobacco

Phenolic compound formation from the low temperature pyrolysis of tobacco

Gas Chromatography Mass Spectrometry Identification of Labile Radicals Formed during Pyrolysis of Catechool, Hydroquinone, and Phenol through Neutral Pyrolysis Product Mass Analysis

Lung carcinogenesis by tobacco smoke

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