Ethyl lauroyl arginate HCl

• CAS: 60372-77-2
• Catalog Number: ACM60372772
• Category: Main Products
• Molecular Weight: 421.02
• Molecular Formula: C20H41ClN4O3
• Synonyms: L-Arginine, N2-(1-oxododecyl)-, ethyl ester, hydrochloride (1:1);Ethyl lauroyl arginate hydrochloride;Ethyl N2-dodecanoyl-L-argininate hydrochloride
• Melting Point: 50.5 - 58 °C
• Appearance: Powder
• Active Content: 95%
• Physical State: Solid

Case Study

Ethyl lauroyl arginate as Broad-Spectrum Antimicrobial Preservative for Food Safety and Preservation

Ma, Yunfang, et al. Frontiers in Microbiology 14 (2023): 1125808.

Ethyl lauroyl arginate, a cationic surfactant derived from L-arginine, lauric acid and ethanol, exerts broad-spectrum antimicrobial activity by disrupting microbial cell membranes and inducing oxidative stress, supporting food preservation and microbiological safety.
Experimental Protocol: Minimum inhibitory and bactericidal concentrations are determined by broth and agar dilution methods against foodborne bacteria, yeasts and molds; biofilm inactivation is evaluated on stainless steel and rubber surfaces using 50-200 μg/mL for 2 hours; produce washing trials employ 0.1% (w/w) solutions for 20 minutes with shaking at 200 rpm or 100 mg/L for 2 minutes at 4-45 degrees Celsius.
Performance Evaluation: Minimum inhibitory concentrations range from 4-100 μg/mL against bacteria (for example 8 μg/mL for Staphylococcus aureus), while yeasts such as Saccharomyces cerevisiae require 35 μg/mL. Biofilms of Listeria monocytogenes, Salmonella and Escherichia coli O157:H7 on stainless steel are reduced by up to 7 log10 CFU/cm², and washing water counts drop by 2.7 to more than 4 log units. Approved as generally recognized as safe up to 200 ppm, the compound prolongs shelf life of meat, produce, dairy and aquatic products while retaining sensory quality.

Ethyl lauroyl arginate HCl as Antimicrobial Preservative for Chilled Storage of Aquatic Products

Zhuang, Shuai, et al. Food Chemistry 324 (2020): 126886.

Ethyl lauroyl arginate hydrochloride serves as a food-grade antimicrobial preservative whose cationic surfactant action suppresses spoilage microbiota, particularly Pseudomonas, thereby extending the chilled shelf life of container-cultured largemouth bass fillets.
Experimental Protocol: Fillets (about 8 cm by 6 cm by 1.5 cm) are immersed in a 0.1% (w/v) solution (pH 5.30) at a 1:1 fish-to-solution weight ratio for 10 minutes, drained, aerobically packaged, and stored at 4 degrees Celsius for up to 11 days; total viable counts, total volatile basic nitrogen, trichloroacetic acid-soluble peptides, ammonia, biogenic amines and 16S rRNA-based microbiota are monitored on days 0, 3, 5, 7, 9 and 11.
Performance Evaluation: Treatment lowers initial counts from 4.55 to 3.59 log CFU/g and reduces bacterial loads by up to 1.61 log CFU/g, prolonging sensory acceptability by 4 days. On day 11, total volatile basic nitrogen reaches 18.0 versus 55.8 mg N/100 g in controls, trichloroacetic acid-soluble peptides 1.86 versus 6.03 μmol tyrosine/g, and histamine 0.35 versus 3.71 mg/kg. The relative abundance of Pseudomonas on day 11 is only 5% versus 58% in untreated fillets, confirming targeted suppression of the main spoilage genus.

Ethyl lauroyl arginate HCl as Antiviral Agent in Nasal Spray for Prevention of SARS-CoV-2 Infection

Thacore, Harshad R., et al. (2021). DOI: 10.21203/rs.3.rs-842564/v1

Ethyl lauroyl arginate hydrochloride acts as an antiviral agent that blocks virus attachment to host cell surfaces through its surfactant properties, supporting a nasal spray formulation for the prevention of SARS-CoV-2 infection.
Experimental Protocol: A recombinant vesicular stomatitis virus pseudotyped with the SARS-CoV-2 spike protein is preincubated with the compound for 1 hour at 37 degrees Celsius before infection of Vero cells; separately, SARS-CoV-2 is incubated with undiluted or 1:1 diluted formula (0.1% active) for 10 minutes at 37 degrees Celsius and administered intranasally (0.05 mL per nare) to Syrian golden hamsters challenged and monitored for 14 days. Human lung fibroblasts are also pretreated with 1-10 μg/mL for 10 minutes before human coronavirus 229E challenge.
Performance Evaluation: Pseudovirus replication is inhibited with a half-maximal effective concentration of 15 μg/mL and complete (over 90%) inhibition at 110 μg/mL. Treated hamsters show no significant weight loss and undetectable subgenomic RNA (below 50 copies), while pretreated cells exhibit markedly reduced viral attachment by scanning electron microscopy and virus yield drops of 0.25-0.5 log10 TCID50/mL, confirming the compound as a promising nasopharyngeal barrier agent.

Custom Q&A

What is the molecular formula of Ethyl lauroyl arginate HCl?

The molecular formula of Ethyl lauroyl arginate HCl is C20H41ClN4O3.

What are the synonyms of Ethyl lauroyl arginate HCl?

The synonyms of Ethyl lauroyl arginate HCl are ethyl lauroyl arginate hydrochloride, 60372-77-2, Cytoguard LA, and XPD6ZY79TB.

What is the molecular weight of Ethyl lauroyl arginate HCl?

The molecular weight of Ethyl lauroyl arginate HCl is 421.0 g/mol.

What is the IUPAC name of Ethyl lauroyl arginate HCl?

The IUPAC name of Ethyl lauroyl arginate HCl is ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride.

What is the InChIKey of Ethyl lauroyl arginate HCl?

The InChIKey of Ethyl lauroyl arginate HCl is CUBZMGWLVMQKNE-LMOVPXPDSA-N.

What is the canonical SMILES of Ethyl lauroyl arginate HCl?

The canonical SMILES of Ethyl lauroyl arginate HCl is CCCCCCCCCCCC(=O)NC(CCCN=C(N)N)C(=O)OCC.Cl.

What is the CAS number of Ethyl lauroyl arginate HCl?

The CAS number of Ethyl lauroyl arginate HCl is 60372-77-2.

How many rotatable bond counts does Ethyl lauroyl arginate HCl have?

Ethyl lauroyl arginate HCl has 18 rotatable bond counts.

What is the topological polar surface area of Ethyl lauroyl arginate HCl?

The topological polar surface area of Ethyl lauroyl arginate HCl is 120Ų.

Is Ethyl lauroyl arginate HCl a covalently-bonded unit?

Yes, Ethyl lauroyl arginate HCl is a covalently-bonded unit with 2 compounds.

Synthetic Use

Downstream Synthesis Route 1

• 60372-77-2
• 127-09-3

• 92071-96-0

Reference: [1]Patent: US8212061,2012,B1 .Location in patent: Page/Page column 5

Downstream Synthesis Route 2

• 60372-77-2
• 629-25-4

• 1193347-26-0

Reference: [1]Patent: US8212061,2012,B1 .Location in patent: Page/Page column 5-6

* For details of the synthesis route, please refer to the original source to ensure accuracy.