Cationic Surfactants from Arginine: Synthesis and Physicochemical Properties

Abstract

The present invention concerns the preparation of cationic surfactants derived from the condensation of an acid chloride, preferably a fatty acid with a number of carbon atoms 8, 9 and 14 with esterified amino acids, preferably basic-type amino acids, like (L)-arginine. The method comprises a first step in which the esterification of the amino acid with an alcohol is performed and a second step for the condensation with a chloride of fatty acid, using Schotten Baumann conditions. These surfactants constitute a novel class of chemicals of low toxicity with excellent surface properties and considerable antimicrobial activity. As in a conventional series of surfactants with different chain lengths, changes in the chain result in changes in the physicochemical properties. Excellent antimicrobial activity is observed for the homologue of 14 carbon atoms.

Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

“…C 11 DMM and dodecanoate can form electrostatically bound heterodimers with very high surface activity [ 26 ]. The CMC value of LAE was at the concentration 1.0–1.1 mmol/dm 3 , in agreement with the value reported in [ 18 ], lower than in other reports (see Table 1 ). The surface tension value at CMC (σ CMC ) was 25 mN/m, much lower than for typical cationic surfactants, closer to σ CMC for nonionic surfactants and characteristic for di-chain or Gemini surfactants [ 27 , 28 ].…”

New antimicrobial self-assembling short lipopeptides

“…This reflects the well-known influence of hydrogen bonding capacity and HLB to enhance the formation of supramolecular structures 21. Additionally, lipopeptides bearing longer aliphatic chains display lower CAC than their shorter counterparts, a trend extensively reported for similar lipopeptides 22.…”

The effects of ethyl lauroyl arginate and lemon essential oil added edible chitosan film coating on biogenic amines formation during storage in mackerel fillets

“…LAE alone is a potent antimicrobial agent, and its incorporation of chitosan has led to the creation of the most effective coating on microbial proliferation even at low doses. The antimicrobial activity of LAE has been associated with a positive charge in its structure (Singare & Mhatre, 2012), but its antimicrobial mechanism has not been fully characterized. Some researchers have suggested that bacterial membranes are the main target of LAE (Becerril et al., 2013; Coronel‐León et al, 2016; Pattanayaiying et al., 2014; Rodriguez et al., 2004).…”