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).
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.
Savelli
M P
MP
Laboratoire de Chimie Organique et Cinétique, Université de Picardie Jules Verne, 33 rue Saint Leu, 80039, Amiens Cedex, France.
Van Roekeghem
P
P
Douillet
O
O
Cavé
G
G
Godé
P
P
Ronco
G
G
Villa
P
P
D003460:Crystallization; D008823:Micelles; D012995:Solubility; D013329:Structure-Activity Relationship; D013816:Thermodynamics; D014993:Xylitol / Q000737:chemistry*
D008823:Micelles; D014993:Xylitol