Home
Resources
Publications
Conformational Interpretation of Vescalagin and Castalagin Physicochemical Properties

Conformational Interpretation of Vescalagin and Castalagin Physicochemical Properties

Nicolas Vivas, Michel Laguerre, Isabelle Pianet de Boissel, Nathalie Vivas de Gaulejac, Marie-Françoise Nonier

J Agric Food Chem. 2004 Apr 7;52(7):2073-8.

PMID: 15053554

Abstract:

Vescalagin and castalagin are two diastereoisomers. The variability of their principal physicochemical properties, compared with their small structural differences, suggests important conformational variations. This study shows, experimentally, that vescalagin has a greater effect on polarity, oxidizability in solution, and thermodegradability than castalagin. Conformational analysis by molecular mechanics demonstrated that vescalagin was more hydrophilic and was more reactive to electrophilic reagents than castalagin. Experimental results were thus explained and demonstrated the distinct behaviors of vescalagin and castalagin. These results were attributed to the C1 position of the two compounds because vescalin and castalin have comparable characteristics. Experimental data were confirmed and interpreted by molecular mechanics. This work represents one of the first attempts to correlate conformation and the properties of phenolic compounds. This step constitutes a predictive method for the pharmacology or chemistry of new compounds.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP24312003	Castalagin		24312-00-3	Price
AP36001475	Vescalagin		36001-47-5	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: