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Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System

Ethyl lauroyl arginate (LAE) is an amino acid-based cationic surfactant with low toxicity and antimicrobial activity. It is widely used as a food preservative and component for food packaging. When stored, LAE decomposes by hydrolysis into surface-active components Nα-lauroyl–l-arginine (LAS) or dod...

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Autores principales: Czakaj, Agnieszka, Jarek, Ewelina, Krzan, Marcel, Warszyński, Piotr
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512375/
https://www.ncbi.nlm.nih.gov/pubmed/34641438
http://dx.doi.org/10.3390/molecules26195894
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author Czakaj, Agnieszka
Jarek, Ewelina
Krzan, Marcel
Warszyński, Piotr
author_facet Czakaj, Agnieszka
Jarek, Ewelina
Krzan, Marcel
Warszyński, Piotr
author_sort Czakaj, Agnieszka
collection PubMed
description Ethyl lauroyl arginate (LAE) is an amino acid-based cationic surfactant with low toxicity and antimicrobial activity. It is widely used as a food preservative and component for food packaging. When stored, LAE decomposes by hydrolysis into surface-active components Nα-lauroyl–l-arginine (LAS) or dodecanoic (lauric) acid. There are only a limited number of reports considering the mechanism of surface activity of LAE. Thus, we analysed the surface tension isotherm of LAE with analytical standard purity in relation to LAE after prolonged storage. We used quantum mechanical density functional theory (DFT) computations to determine the preferred hydrolysis path and discuss the possibility of forming highly surface-active heterodimers, LAE-dodecanoate anion, or LAE-LAS. Applying molecular dynamics simulations, we determined the stability of those dimers linked by electrostatic interactions and hydrogen bonds. We used the adsorption model of surfactant mixtures to successfully describe the experimental surface tension isotherms. The real part surface dilational modulus determined by the oscillation drop method follows a diffusional transport mechanism. However, the nonlinear response of the surface tension could be observed for LAE concentration close to and above Critical Micelle Concentration (CMC). Nonlinearity originates from the presence of micelles and the reorganisation of the interfacial layer.
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spelling pubmed-85123752021-10-14 Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System Czakaj, Agnieszka Jarek, Ewelina Krzan, Marcel Warszyński, Piotr Molecules Article Ethyl lauroyl arginate (LAE) is an amino acid-based cationic surfactant with low toxicity and antimicrobial activity. It is widely used as a food preservative and component for food packaging. When stored, LAE decomposes by hydrolysis into surface-active components Nα-lauroyl–l-arginine (LAS) or dodecanoic (lauric) acid. There are only a limited number of reports considering the mechanism of surface activity of LAE. Thus, we analysed the surface tension isotherm of LAE with analytical standard purity in relation to LAE after prolonged storage. We used quantum mechanical density functional theory (DFT) computations to determine the preferred hydrolysis path and discuss the possibility of forming highly surface-active heterodimers, LAE-dodecanoate anion, or LAE-LAS. Applying molecular dynamics simulations, we determined the stability of those dimers linked by electrostatic interactions and hydrogen bonds. We used the adsorption model of surfactant mixtures to successfully describe the experimental surface tension isotherms. The real part surface dilational modulus determined by the oscillation drop method follows a diffusional transport mechanism. However, the nonlinear response of the surface tension could be observed for LAE concentration close to and above Critical Micelle Concentration (CMC). Nonlinearity originates from the presence of micelles and the reorganisation of the interfacial layer. MDPI 2021-09-29 /pmc/articles/PMC8512375/ /pubmed/34641438 http://dx.doi.org/10.3390/molecules26195894 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Czakaj, Agnieszka
Jarek, Ewelina
Krzan, Marcel
Warszyński, Piotr
Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title_full Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title_fullStr Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title_full_unstemmed Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title_short Ethyl Lauroyl Arginate, an Inherently Multicomponent Surfactant System
title_sort ethyl lauroyl arginate, an inherently multicomponent surfactant system
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8512375/
https://www.ncbi.nlm.nih.gov/pubmed/34641438
http://dx.doi.org/10.3390/molecules26195894
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