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Fluorescence Emitted During the Autooxidation of 2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one

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Abstract

Data suggest that the purpurogallin (2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one, hydroxybenzotropolone) and its analogues formed from the polyphenols can be precursors of the most complex natural compounds—humic acids and melanin-like polymers. Therefore, to confirm this possibility, the autooxidation of purpurogallin to humus-like substances has been performed. The oxidation process has been assayed by means of fluorescence and UV/VIS absorption spectroscopy. The obtained results indicate that purpurogallin undergoes a free-radical-mediated autooxidation via purpurogallinquinones to humus-like polymers. The scheme of the complex transformation of purpurogallin has been proposed.

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REFERENCES

  1. J. Slawinski (1971) Photochem. Photobiol. 13, 489–497.

    Google Scholar 

  2. D. Slawinska, K. Lichszteld, and T. Michalska (1978) Polish. J. Chem. 52, 1729–1740.

    Google Scholar 

  3. J. Slawinski, B. Szczodrowska, and M. Wodarczyk-Graetzer (1973) Acta Biochim. Polon. 20(2), 119–13

    Google Scholar 

  4. K. Prasad, R. Kapoor, and P. Lee (1994) Mol. Cell. Biochem. 139, 27–32.

    Google Scholar 

  5. T. Wu, L. Zeng, J. Wu, K. Fung, R. Weisel, A. Hempel, and N. Camerman (1996) Biochem. Pharm. 52, 1073–1080

    Google Scholar 

  6. D. Rootman, R. Bindish, L. Zeng, S. Hasany, and T. Wu (1994) J. Opthalmol. 29, 220–223.

    Google Scholar 

  7. R. Nilsson (1964) Acta Chem. Scand. 19, 389–401.

    Google Scholar 

  8. S. V. Jovanovic, Y. Hara, S. Steenken, M. G. Simic (1997) J. Am. Chem. Soc. 119, 5337–5343.

    Google Scholar 

  9. D. Slawinska, J. Slawinski, and T. Sarna (1975) Photochem. Photobiol. 21, 393–396.

    Google Scholar 

  10. H.-R. Schulten (1995) Fres. J. Anal. Chem. 351, 62–73.

    Google Scholar 

  11. M. Lipski, J. Slawinski, and D. Zych (1999) J. Fluoresc. 9, 133–138.

    Google Scholar 

  12. J. Auger, C. Richard (1996) J. Photochem. Photobiol. A:Chem. 93, 193–198.

    Google Scholar 

  13. D. Slawinska, J. Slawinski, and T. Sarna (1975) Soil Sci. 26, 127–131.

    Google Scholar 

  14. M. Lipski, H. Manikowski, and J. Slawinski (1997) in Application of Magnetic Resonance in Chemistry and Related Areas,Warszawa, pp. C–10.

  15. N. Senesi and T. Miano (1994) Humic Substances in the Global Environment and Implications on Human Health, Elsevier, Amster-dam, pp. 3–386.

    Google Scholar 

  16. M. Cheshire, C. Bedrock, D. McPhail, and A. Fraser (1997) in J. Drozd, S. Gonet, N. Senesi, J. Weber (Eds.) The Role of Humic Substances in the Ecosystems and in Environmental Protection, Wroclaw, pp. 309–314.

  17. M. Lipski, H. Manikowski, R. Skwarek, and J. Slawinski (2000) in International Conference on Photobiophysics in Technology and Medicine, Pozna, p. P16

  18. M. Lipski, K. Gwozdzinski, and J. Slawinski (2000) Curr. Topics Biophys. 24(2), pp. 115–120.

    Google Scholar 

  19. M. Lipski, J. Slawinski, H. Manikowski, and Z. Górski (1997) Eur. J. Clin. Chem. Clin. Biochem. 9(A), 87.

    Google Scholar 

  20. Z. Górski, M. Lipski, D. Slawinska, and J. Slawinski (1997) in XVIIIth International Conference on Photochemistry, Warszawa, p. 3P37.

  21. D. Slawinska and J. Slawinski (1967) Nature, 213, 902–903.

    Google Scholar 

  22. J. Glebska and K. Gwozdzinski (1998) Curr. Topics Biophys. 22, 27–55.

    Google Scholar 

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Authors and Affiliations

  1. Department of Radio & Photochemistry, Institute of Chemistry & Technical Electrochemistry, Faculty of Chemical Technology, Poznan University of Technology, Piotrowo 3 str., 60-965, Poznan, Poland

    M. Lipski

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  1. M. Lipski
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Lipski, M. Fluorescence Emitted During the Autooxidation of 2,3,4,6-tetrahydroxy-5H-benzocyclohepten-5-one. Journal of Fluorescence 12, 83–86 (2002). https://doi.org/10.1023/A:1015319405245

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  • DOI: https://doi.org/10.1023/A:1015319405245

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