Ethyl lauroyl arginate Hcl or Ethyl lauroyl arginate hydrochloride is a chemical compound based on amino acids, synthesised through esterification and condensation processes.

It appears as a fine, white powder, soluble in water, ethanol, propylene glycol and glycerol.

What it is used for and where

Chemical intermediate.

Food

It is used as an antimicrobial food additive in the sanitisation of preserved foods, approved in the USA, Mexico, Canada and the European Union in 2014 for heat-treated meat products (except emulsified sausages, smoked sausages and liver paste) at levels up to 160 mg/kg.

Its efficacy against Staphylococcus aureus, Listeria innocua, Escherichia coli, Pseudomonas aeruginosa, Salmonella enterica has been established by numerous studies (1) and so has its activity against moulds, yeasts, gram-positive and gram-negative bacteria whose microbial death occurs within 1 hour of contact (2).

Cosmetics

Used as an antimicrobial preservative. It is a restricted ingredient as a III/197 and V/58 Relevant Item in the Annexes of the European Cosmetics Regulation 1223/2009

Safety

Ethyl lauroyl arginate Hcl is believed to be innocuous: it is metabolised in the human body into the ethyl ester arginine and Nα-lauroyl-L-arginine and subsequently arginine, ethanol and lauric acid (EFSA 2007). In both in vitro and in vivo techniques, Ethyl lauroyl arginate Hcl was rapidly metabolised to the natural dietary components lauric acid and arginine (3). 

For more information:

Ethyl lauroyl arginate Hcl studies

Typical commercial product characteristics Ethyl lauroyl arginate HCl

Appearance	White powder
Melting point	60.9-61.4℃
pH	3.0-5.0
PSA	120.79000
LogP	6.05170
N-lauroyl-L-arginine	3% max
Lauric acid	5% max
Ethyl laurate	3% max
L-Arginine HCl	1% max
Ethyl arginine.2HCl	1% max
Arsenic	3mg/kg max
Lead	1mg/kg max
Mercury	1mg/kg max
Cadmium	1mg/kg max
Water content	≤5.0%
Storage	Room temperature
Shelf Life	2 years
Safety

• Molecular Formula   C₂₀H₄₁ClN₄O₃     C₂₀H₄₁ClN₄O₃  · HCl
• Molecular Weight     421.0
• Exact Mass    420.286713
• CAS  60372-77-2
• UNII    XPD6ZY79TB
• EC Number   207-949-1     434-630-6
• DSSTox Substance ID  DTXSID40209136
• IUPAC  ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride
• InChI=1S/C20H40N4O3.ClH/c1-3-5-6-7-8-9-10-11-12-15-18(25)24-17(19(26)27-4-2)14-13-16-23-20(21)22;/h17H,3-16H2,1-2H3,(H,24,25)(H4,21,22,23);1H/t17-;/m0./s1  
• InChl Key      CUBZMGWLVMQKNE-LMOVPXPDSA-N
• SMILES   CCCCCCCCCCCC(=O)NC(CCCN=C(N)N)C(=O)OCC.Cl
• MDL number  
• PubChem Substance ID    
• NACRES NA.22 
• RXCUI     1426162
• RIDADR    UN 3077 9 / PGIII

Synonyms

• Cytoguard LA
• Ethyl lauroyl arginate HCl
• ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride
• lauroyl ethyl arginate hydrochloride
• Ethyl Lauroyl Arginate HCl Lauric Arginate
• ethyl N-lauroyl-L-arginate hydrochloride
• Ethyl N-dodecanoyl-L-argininate hydrochloride (1:1)

References_______________________________________________________________________

(1) Becerril, R., Manso, S., Nerin, C., & Gómez-Lus, R. (2013). Antimicrobial activity of Lauroyl Arginate Ethyl (LAE), against selected food-borne bacteria. Food Control, 32(2), 404-408.

Nübling, S., Wohlt, D., Saile, N., Weiss, A., & Schmidt, H. (2017). Antimicrobial effect of lauroyl arginate ethyl on Escherichia coli O157: H7 and Listeria monocytogenes on red oak leaf lettuce. European Food Research and Technology, 243(5), 879-887.

(2) Nerin, C., Becerril, R., Manso, S., & Silva, F. (2016). Ethyl lauroyl arginate (LAE): Antimicrobial activity and applications in food systems. In Antimicrobial food packaging (pp. 305-312). Academic Press.

(3) Hawkins DR, Rocabayera X, Ruckman S, Segret R, Shaw D. Metabolism and pharmacokinetics of ethyl N(alpha)-lauroyl-L-arginate hydrochloride in human volunteers. Food Chem Toxicol. 2009 Nov;47(11):2711-5. doi: 10.1016/j.fct.2009.07.028.