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New lipophilic catechin derivatives by oxa-Pictet-Spengler reaction

  • Bouddah Poaty
  • Stéphane Dumarçay
  • Dominique Perrin
Original Paper

Abstract

Synthesis of lipophilic catechin derivatives was carried out to improve their solubility in lipidic substances that must be protected against oxidation. For this purpose, an oxa-Pictet-Spengler coupling reaction, which is not only conservative for antioxidative activity, but also simple, mild and inexpensive, was applied. This method permitted grafting of alkyl chains, from various methyl ketones, between the C and B rings of catechin. The derivatives were isolated, on the one hand, by silica gel column chromatography and, on the other, by simple aqueous washing of the crude product. Both treatments produced almost the same purity; products of the second one had best antioxidative activities given by inhibition of the induced oxidation of methyl linoleate and by reactivity with the free radical 2,2-diphenyl-picrylhydrazyl. All derivatives acquired a lipophilic character as proven by measurement of the partition coefficient between octanol and water.

Keywords

Catechin Antioxidative activity Oxa-Pictet-Spengler reaction Lipophilic derivatives Log P 

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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Bouddah Poaty
    • 1
  • Stéphane Dumarçay
    • 1
  • Dominique Perrin
    • 1
  1. 1.Laboratoire d’Etudes et de Recherche sur le Matériau Bois, IFR 110, Faculté des Sciences et TechniquesNancy-UniversitéVandœuvre-lès-NancyFrance

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