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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2021
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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. |
format | Online Article Text |
id | pubmed-8512375 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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