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 = Cn H2n+1, n = 4-17). A classical decrease of critical micelle concentration wi th the increase in the alkyl chain has been found. With water, esters displ ayed lamellar phases at temperatures of 25 degrees C or higher. The extent of hydrophilic/lipophilic balance range obtained by emulsification method c an be proven to be of interest for pharmaceutical applications. The results were compared with those obtained in previous investigations, i.e. for alk yl-substituted xylitol, with thioether (Z = S) and ether (Z = O) linking gr oups in order to discuss the role of the junction nature. Likewise, they we re compiled with the results related to their D-glucose homologues, in orde r to put forward the effects of the head group configuration, cyclic or acy clic. (C) 1999 Elsevier Science B.V. All rights reserved.