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

Huiling Lu; Audrey Drelich; Mehdi Omri; Isabelle Pezron; Anne Wadouachi; Gwladys Pourceau

doi:10.3390/molecules21101301

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

Molecules. 2016 Sep 28;21(10):1301. doi: 10.3390/molecules21101301.

Authors

Huiling Lu¹, Audrey Drelich², Mehdi Omri³, Isabelle Pezron⁴, Anne Wadouachi⁵, Gwladys Pourceau⁶

Affiliations

¹ TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. huiling.lu@utc.fr.
² TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. audrey.drelich@utc.fr.
³ LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. mehdi.omri@u-picardie.fr.
⁴ TIMR EA 4297 UTC/ESCOM, Sorbonne University, University of Technology of Compiègne, Rue Personne de Roberval, Compiègne CEDEX 60200, France. isabelle.pezron@utc.fr.
⁵ LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. anne.wadouachi@u-picardie.fr.
⁶ LG2A, UMR CNRS 7378-Chemistry Institute of Picardy FR CNRS 3085, University of Picardy Jules Verne, 33 rue Saint Leu, Amiens CEDEX 80039, France. gwladys.pourceau@u-picardie.fr.

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 (γ_cmc), solubility, and Krafft temperature were measured, and the effect of structural modifications on surface active properties and micelle formation was discussed.

Keywords: TEMPO mediated oxidation; carbohydrate-based surfactants; sugar esters; uronic acids derivatives.