title: Effects of tail alkyl chain length (n), head group structure and junction (Z) on amphiphilic properties of 1-Z-R-D,L-xylitol compounds (R = CnH2n+1).
abstract: In the family of 1-Z-R-D,L-xylitol, we have determined the main amphiphilic properties of esters (Z = OCO) as a function of alkyl chain length (R = CnH2n+1, n = 4-17). A classical decrease of critical micelle concentration with the increase in the alkyl chain has been found. With water, esters displayed lamellar phases at temperatures of 25 degrees C or higher. The extent of hydrophilic/lipophilic balance range obtained by emulsification method can be proven to be of interest for pharmaceutical applications. The results were compared with those obtained in previous investigations, i.e. for alkyl-substituted xylitol, with thioether (Z=S) and ether (Z=O) linking groups in order to discuss the role of the junction nature. Likewise, they were compiled with the results related to their D-glucose homologues, in order to put forward the effects of the head group configuration, cyclic or acyclic.
authors.affiliation: Laboratoire de Chimie Organique et Cinétique, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
authors.forename: M P
authors.initials: MP
authors.lastname: Savelli
authors.forename: P
authors.initials: P
authors.lastname: Van Roekeghem
authors.forename: O
authors.initials: O
authors.lastname: Douillet
authors.forename: G
authors.initials: G
authors.lastname: Cavé
authors.forename: P
authors.initials: P
authors.lastname: Godé
authors.forename: G
authors.initials: G
authors.lastname: Ronco
authors.forename: P
authors.initials: P
authors.lastname: Villa
mesh_terms: D003460:Crystallization; D008823:Micelles; D012995:Solubility; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014993:Xylitol / Q000737:chemistry*
chemical_list: D008823:Micelles; D014993:Xylitol