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Issue 0, 1980
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Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight

Abstract

Homogeneous polymeric proanthocyanidins have been isolated from 22 plant sources and all are based on a C(4)–C(8)[or C(6)] linked polyflavan-3-ol structure. 13C N.m.r, spectroscopy in 2[H6]acetone–water is used to calculate the ratio of procyanidin to prodelphinidin monomer units, the average heterocyclic ring stereochemistry of the monomers, and the ratio of monomers to chain-terminating units. The majority of polymers isolated in this study possess monomers with predominantly a 2,3-cis stereochemistry [the same configuration as (–)-epicatechin]. The number-average molecular weight, calculated from monomer to terminal unit ratios, of the polymers is 1 500–5 000. The structure of the chain-terminating group is established by thiolysis degradation and g.l.c. analysis of the products.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1980, 2278-2286
Article type
Paper

Polymeric proanthocyanidins. Stereochemistry, structural units, and molecular weight

Z. Czochanska, L. Y. Foo, R. H. Newman and L. J. Porter, J. Chem. Soc., Perkin Trans. 1, 1980, 2278
DOI: 10.1039/P19800002278

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