Surfactants Derived from Amino Acids. III.

Some Surface Active Properties and Antimicrobial Activities of Salts of Long Chain N ^α-Acyl-L-arginine Esters

Abstract

Long chain N^α-acyl-L-arginines obtained by the reactions of the C₁₀-C₁₆ fatty acid chlorides with L-arginine, were esterified by ethyl alcohol containing dry hydrogen chloride to yield salts of long chain N^α-acyl-L-arginine esters. To examine their surface active properties and antimicrobial activities, Krafft point, pH value, critical micelle concentration, surface tention, foaming power, wetting and emulsifying properties and minimum inhibition concentration (MIC) were measured and these data were compared with those of benzyldimethyl {2- [2 (p-1, 1, 3, 3-tetramethylbutylphenoxy) ethoxy] ethyl} ammonium chloride (benzethonium chloride). Among the salts of long chain N^α-acyl-L-arginine esters, the lauroyl derivatives showed best surface active properties and antimicrobial activities, and had almost the same properties as those of benzethonium chloride. The hydrolysis properties of the salts of N^α-acyl-L-arginine esters were also examined.