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Oxidation and Rearrangement Reactions of Condensed Tannins

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Plant Polyphenols

Part of the book series: Basic Life Sciences ((BLSC,volume 59))

Abstract

The chemistry of condensed tannins at alkaline pH is regulated by the formation of A- and/or B-ring quinone-methides as highly reactive intermediates. The former group of electrophilic species is of special significance in analogues with 5,7-dihydroxy A-ring functionality and may be successfully trapped by external nucleophiles such as phenolic nuclei and thiols. B-ring quinone-methides may similarly be trapped but are preferentially susceptible to intramolecular trapping to give analogues with rearranged pyran heterocycles. A mechanistic rationale to explain the base-catalyzed rearrangement reactions and the oxidative conversion of B- to A-type proanthocyanidins is proposed. These reactions are of relevance to the industrial application of condensed tannins.

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Authors and Affiliations

  1. Department of Chemistry, University of the Orange Free State, Bloemfontein, 9300, South Africa

    Daneel Ferreira, Jan P. Steynberg, Johann F. W. Burger & Barend C. B. Bezuidenhoudt

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  3. Johann F. W. Burger
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  1. United States Department of Agriculture, Forest Service, Pineville, Louisiana, USA

    Richard W. Hemingway

  2. Institute of Wood Research, Houghton, Michigan, USA

    Peter E. Laks

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Ferreira, D., Steynberg, J.P., Burger, J.F.W., Bezuidenhoudt, B.C.B. (1992). Oxidation and Rearrangement Reactions of Condensed Tannins. In: Hemingway, R.W., Laks, P.E. (eds) Plant Polyphenols. Basic Life Sciences, vol 59. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3476-1_20

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