Catalog NumberHG60372772
CAS Number60372-77-2
CategoryCationic Surfactants
Use as antistatic agent.
Use as preservative.
Ethyl Lauroyl Arginate: Multicomponent Surface-Active Behavior and Implications for Formulation
Czakaj, Agnieszka, et al. Molecules 26.19 (2021): 5894.
This work clarified the surface-activity mechanisms, aggregation behavior, and storage-related transformations of ethyl lauroyl arginate (LAE) to inform its use as a low-toxicity, antimicrobial surfactant in food, cosmetic and biomedical formulations.
· Multicomponent nature of LAE solutions: Fresh LAE solutions can contain small amounts of surface-active synthesis residues (dodecanoic/lauric acid) and, upon prolonged storage, undergo base-catalysed hydrolysis yielding Nα-lauroyl-l-arginine (LAS). Model fits assumed ~0.2% dodecanoic acid in fresh LAE solution and ~18% LAS after extended hydrolysis. IR spectroscopy supported production of LAS.
· Surface activity characteristics: The measured surface tension isotherm places LAE's surface activity between that of a cationic surfactant and a nonionic surfactant having the same hydrophobic tail length.
· Dimer formation and stability: DFT energetics and MD simulations indicate feasible formation of highly surface-active heterodimers (LAE-dodecanoate anion and LAE-LAS) stabilized by electrostatic attraction, hydrogen bonding (LAE-dodecanoate), and guanidinium-group interactions/stacking (LAE-LAS). These dimers contribute to observed interfacial behavior.
· Interfacial dynamics: The real part of the surface dilational modulus follows a diffusional transport mechanism at most concentrations, consistent with adsorption-controlled interfacial exchange.
· Nonlinear interfacial response near/above CMC: At LAE concentrations close to and above the critical micelle concentration, the surface tension response becomes nonlinear; this nonlinearity was attributed to micelle presence and reorganization of the interfacial surfactant layer during dynamic perturbation.
Incorporation of Ethyl Lauroyl Arginate HCl into Electrospun PLA Films for Antimicrobial Food Packaging
Li, Ting, et al. Food Control 130 (2021): 108371.
This study explored the use of Ethyl-Nα-dodecanoyl-L-arginate hydrochloride (LAE·HCl) as an antimicrobial additive in biodegradable electrospun poly(lactic acid) (PLA) films and assess the films' structure, thermal/intermolecular properties, antimicrobial activity, and effectiveness in preserving fresh strawberries at 25 °C.
Fabrication: Electrospun films were fabricated with LAE concentrations of 0.5% to 2.0% (w/v). The LAE was first dispersed in a solvent system and then blended with PLA to form a homogeneous film-forming solution. This solution was electrospun into ultra-fine nanofibers under controlled processing parameters, including a specific voltage and flow rate, to ensure consistent fiber formation.
Key Results:
· Fiber morphology & size: LAE-loaded nanofibers had average diameters of 325-364 nm, representing a 43.5%-49.5% reduction in diameter relative to neat PLA fibers.
· Intermolecular interaction & thermal stability: The films' intermolecular interactions and thermal behavior were characterized, indicating modified microstructure in LAE-containing mats versus PLA alone.
· Antimicrobial performance: LAE-containing electrospun films exhibited strong antimicrobial activity against Escherichia coli O157:H7, Staphylococcus aureus, and the fungal spoilage organism Botrytis cinerea, as demonstrated in the study's microbiological assays.
· Application test: Packaging strawberries with the LAE-enriched PLA electrospun films effectively extended shelf life at 25 °C, supporting the feasibility of these active, biodegradable films for fresh-produce preservation under the conditions tested.
Enhancing Oral Bioavailability of Rosmarinic Acid Using Ethyl Lauroyl Arginate Hydrophobic Ion Pairing
Gad, Heba A., et al. International Journal of Pharmaceutics 630 (2023): 122388.
This study explored the use of Ethyl lauroyl arginate (ELA), an amino acid-based cationic surfactant, to improve the oral delivery of Rosmarinic acid (RM), a biologically active polyphenol with poor permeability and low bioavailability. By forming a hydrophobic ion pair (HIP) complex between ELA and RM and encapsulating it into lipid nanocapsules (LNCs), the work aimed to enhance RM's lipophilicity, intestinal absorption, and systemic exposure.
Preparation: The HIP complex was formed by combining RM and ELA at various molar ratios. A 1:2 RM:ELA ratio was identified as optimal, demonstrating high complexation efficiency and a significant increase in lipophilicity. The optimized HIP complex was subsequently encapsulated into lipid nanocapsules (LNCs) to create a final oral dosage form.
Key Performance:
· Enhanced Permeability: Ex vivo intestinal permeation studies using porcine intestine revealed cumulative RM permeation per area after 6 hours of 3.79 ± 0.57 µg/cm2 for the RM-ELA HIP, and 5.71 ± 0.32 µg/cm2 for the LNC formulation. These results confirmed that both the HIP complex and the LNC system substantially improved RM's permeability compared to RM alone.
· Improved Pharmacokinetics: Plasma concentration-time profiles of RM demonstrated a significant increase in bioavailability. The Cmax values were in the order of LNC (61.33 ± 8.89 ng/mL) > HIP (42.13 ± 11.22 ng/mL) > RM solution (20.96 ± 3.12 ng/mL). The relative total plasma exposure (AUC) was 1.46-fold higher for HIP and 1.88-fold higher for LNCs compared with free RM.