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Chemistry and Significance of Condensed Tannins pp 265–283Cite as

Reactions at the Interflavanoid Bond of Proanthocyanidins

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Abstract

Condensed tannins with a 5,7-dihydroxy A-ring are particularly suscep­tible to interflavanoid bond cleavage under either acidic or basic condi­tions. The lability of the interflavanoid bond in this class of tannins has been important in development of analytical tools for determination of their structure and for their synthesis. The greatest hope for the use of condensed tannins of the 5,7-dihydroxy class as a renewable source of specialty chemicals lies in exploitation of the lability of the interfla­vanoid bond. Examples include the synthesis of tannin derivatives for use in cold-setting phenolic resins and biocides. Reductive cleavage of­fers the potential for production of significant yields of flavan-3-ols and low molecular weight proanthocyanidins. Cleavage of the interflavanoid bond with sulfite ion under mild acidic or alkaline conditions produces flavan-and oligomeric procyanidin-4-sulfonates that are useful interme­diates for formulation of fast-setting adhesives. We are just beginning to learn how to use base-catalyzed cleavage reactions to our advantage. It can be anticipated that novel uses will be developed from both acid-and base-catalyzed cleavage products of condensed tannins as further understanding of these reactions is obtained.

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Authors and Affiliations

  1. Southern Forest Experiment Station, USDA Forest Service, Pineville, Louisiana, 71360, USA

    Richard W. Hemingway

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  1. Richard W. Hemingway
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Editors and Affiliations

  1. United States Department of Agriculture, Pineville, Louisiana, USA

    Richard W. Hemingway

  2. Oregon State University, Corvallis, Oregon, USA

    Joseph J. Karchesy

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© 1989 Plenum Press, New York

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Hemingway, R.W. (1989). Reactions at the Interflavanoid Bond of Proanthocyanidins. In: Hemingway, R.W., Karchesy, J.J., Branham, S.J. (eds) Chemistry and Significance of Condensed Tannins. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-7511-1_16

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  • DOI: https://doi.org/10.1007/978-1-4684-7511-1_16

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