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The important role of quinic acid in the formation of phenolic compounds from pyrolysis of chlorogenic acid

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Abstract

Chlorogenic acid and its two structural components, quinic acid and caffeic acid, were pyrolyzed under reaction conditions simulating the typical pyrolysis conditions inside a burning cigarette. Major phenolic products from pyrolysis of the three acids were quantified and compared to evaluate the respective contribution of the quinic and caffeic acid moieties to the overall phenolic yield in chlorogenic acid pyrolysis. The results show that the most prominent phenolic product of chlorogenic acid is catechol, followed in order by phenol, hydroquinone, and alkylcatechols. Among these phenolics, catechol and alkylcatechols are formed mainly from the caffeic acid moiety of chlorogenic acid, while phenol and hydroquinone are produced predominantly from the quinic acid moiety. The quinic acid moiety can thus contribute more than 40 % of the overall phenolic yields in chlorogenic acid pyrolysis (0.54 mol mol−1 chlorogenic acid pyrolyzed at 600 °C). Because considerable amounts of free quinic acid and its derivatives exist in tobacco, the results of this study indicate that quinic acid can be an important source of phenolic compounds, especially hydroquinone and phenol, in tobacco smoke.

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Acknowledgments

This research is supported by the Funding of Shanghai Tobacco (Group) Corporation (2011-1-010), a grant from the NSFC project (51008175), and the National Special Program of Water Pollution Control and Management (No. 2012ZX07301-005).

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Authors and Affiliations

  1. State Key Laboratory of Chemical Resource Engineering, Beijing University of Chemical Technology, Beijing, 100029, China

    Zhihua Wang & Xiaoliang Li

  2. Shanghai Tobacco (Group) Corporation, Shanghai, 200082, China

    Saijing Zhen

  3. State Key Joint Laboratory of Environmental Simulation and Pollution Control, School of Environment, Tsinghua University, Beijing, 100084, China

    Xiangyu Li, Chengwen Wang & Yujue Wang

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  1. Zhihua Wang
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  2. Xiaoliang Li
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  3. Saijing Zhen
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  4. Xiangyu Li
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  5. Chengwen Wang
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  6. Yujue Wang
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Correspondence to Yujue Wang.

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Wang, Z., Li, X., Zhen, S. et al. The important role of quinic acid in the formation of phenolic compounds from pyrolysis of chlorogenic acid. J Therm Anal Calorim 114, 1231–1238 (2013). https://doi.org/10.1007/s10973-013-3142-z

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  • DOI: https://doi.org/10.1007/s10973-013-3142-z

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