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Molecules 2016, 21(10), 1301; doi:10.3390/molecules21101301

Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties

1
TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France
2
LG2A, UMR CNRS 7378—Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France
*
Author to whom correspondence should be addressed.
Academic Editors: Christophe Len and Derek J. McPhee
Received: 27 July 2016 / Revised: 13 September 2016 / Accepted: 22 September 2016 / Published: 28 September 2016
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Abstract

Large quantities (>3 g) of a new series of alkyl uronates were synthesized in two steps from commercial methyl hexopyranosides. Firstly, several tens of grams of free methyl α-d-glucopyranoside were selectively and quantitatively oxidized into corresponding sodium uronate using 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (TEMPO)-catalyzed oxidation. Hydrophobic chains of different length were then introduced by acid-mediated esterification with fatty alcohols (ethyl to lauryl alcohol) leading to the desired alkyl glucuronates with moderate to good yields (49%–72%). The methodology was successfully applied to methyl α-d-mannopyranoside and methyl β-d-galactopyranoside. Physicochemical properties, such as critical micelle concentration (CMC), equilibrium surface tension at CMC (γcmc), solubility, and Krafft temperature were measured, and the effect of structural modifications on surface active properties and micelle formation was discussed. View Full-Text
Keywords: carbohydrate-based surfactants; uronic acids derivatives; sugar esters; TEMPO mediated oxidation carbohydrate-based surfactants; uronic acids derivatives; sugar esters; TEMPO mediated oxidation
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Lu, H.; Drelich, A.; Omri, M.; Pezron, I.; Wadouachi, A.; Pourceau, G. Catalytic Synthesis of a New Series of Alkyl Uronates and Evaluation of Their Physicochemical Properties. Molecules 2016, 21, 1301.

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