A comparative study of the permeation of dihexadecyl phosphate vesicles by various carboxylic acids and some of their tetrazole analogues

Synthesis of New Heterocyclic Fatty Compounds

“…Pernice et al reported on 5-undecyl-1H-tetrazole (1) in a study concerning the permeation properties of carboxylic acids and their tetrazole analogues without giving any data for the characterization of the compound. [10] Although tetrazole 2 is documented in CAS, a reference is missing, indicating that the compound is the subject of a patent. To provide the alkyl-branched tetrazole 7, methyl oleate (8) was treated with iodoacetonitrile in the presence of copper powder in a free radical reaction [11] (Scheme 1).…”

Synthesis of New Heterocyclic Fatty Compounds.

“…By the method of Koguro et al [9] we converted various fatty nitriles into the corresponding 5-alkyl-1H-tetrazoles by use of 3 equiv. [10] Although tetrazole 2 is documented in CAS, a reference is missing, indicating that the compound is the subject of a patent. The reaction was performed in about 2 d at reflux temperature, after which the reaction mixture was dissolved in water and the layers were separated.…”

New method for the determination of permeation coefficients of functional chemical groups using membrane model vesicles

“…Hexyltetrazole has already been described in a previous paper (14). The other chemicals dimethylsulfoxide (DMSO), R~( b p y )~C 1~6 H~O were purchased from Aldrich Chemicals.…”

“…Let us start by pointing out the selection of the hexane series for this study, because of our recent results (14). In this work, we have showed that carboxylic acids having a carbon chain length from 5 to 8 carbon atoms induced vesicle membrane perturbations the magnitude of which is controlled by two parameters -carbon chain length and the carboxylic function while for carboxylic acids having a carbon chain length of more than 10 carbon atoms, the perturbing effect is mainly under the control of the carbon chain length, the contribution of the functional group to the perturbing effect is very low and not suitable for the purpose of this work.…”