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Synthesis and structural characterization of oaklin-catechins.

André Sousa¹, Ana Fernandes, Nuno Mateus

¹Departamento de Química, Faculdade de Ciências, Universidade do Porto, Centro de Investigação em Química, Rua do Campo Alegre 687, 4169-007 Porto, Portugal.

Journal of Agricultural and Food Chemistry

|January 17, 2012

Summary

Procyanidin dimer B4 reacts with oak wood cinnamic aldehydes to form new colored compounds. This study elucidates the formation of these oaklin-catechin adducts, highlighting procyanidins

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Quantitative 31P NMR Analysis of Lignins and Tannins

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Area of Science:

* Food Chemistry
* Organic Chemistry
* Analytical Chemistry

Background:

* Procyanidins are key phenolic compounds in oak wood.
* Cinnamic aldehydes are extracted from oak during aging.
* Understanding reactions between these compounds is crucial for wine and spirits quality.

Purpose of the Study:

* To investigate condensation reactions between procyanidin dimer B4 and oak wood cinnamic aldehydes.
* To elucidate the formation mechanism of resulting adducts.
* To demonstrate the role of procyanidins in color formation.

Main Methods:

* Condensation reactions conducted in winelike model solutions.
* Analysis of reaction products using mass spectrometry (m/z 737 and 767).
* Structural characterization of guaiacylcatechin-pyrylium-catechin (GCP-catechin) using 1D and 2D NMR.

Main Results:

* Coniferaldehyde formed guaiacylcatechin-pyrylium-catechin (GCP-catechin, 737 m/z).
* Sinapaldehyde formed syringylcatechin-pyrylium-catechin (SCP-catechin, 767 m/z).
* NMR confirmed the structure of GCP-catechin and provided insights into the formation mechanism.

Conclusions:

* Procyanidins react with oak cinnamic aldehydes to form novel colored compounds.
* The study elucidates the formation pathway of these oaklin-catechin adducts.
* Procyanidins are important contributors to color development in aged oak-derived beverages.