ETHYL LAUROYL ARGINATE

CAS Number: 60372-77-2 (also 88674-34-8 for the hydrochloride salt)
 Synonyms: Ethyl N²-lauroyl-L-arginate hydrochloride; LAE; E243; Ethyl lauroyl arginate HCl; Lauric arginate ethyl ester; Lauroyl ethyl arginate; LAE hydrochloride
Physical Properties:
Appearance: White to off-white, free-flowing powder or granular solid (hydrochloride salt form).
Solubility: Freely soluble in water (> 250 g/L at 20°C); soluble in propylene glycol, glycerol, ethanol; slightly soluble in oils.
Molecular weight: 421.02 g/mol (free base); 457.48 g/mol (as HCl salt).
Melting point: 50-58°C (decomposes gradually above 60°C).
pH (1% solution in water): 3.5–5.0 (acidic due to HCl salt and arginine guanidinium group).
Partition coefficient (log P): 2.1 (moderately lipophilic, allows membrane interaction).
Surface activity: Cationic surfactant (similar to quaternary ammonium compounds).
Stability: Stable at pH 3–7 and up to 80°C; hydrolyzes under strongly alkaline conditions (pH > 9) or prolonged high temperature to lauric acid and ethyl arginine. Stable in typical food processing (pasteurization, UHT).
Zeta potential: Positive charge in solution (cationic).
Applications:
Meat and poultry products: Fresh ground beef (80/20), ground pork, fresh sausages, hot dogs, deli meats, marinated raw poultry, and cooked ham. Typical use: 50–200 ppm alone or with sodium diacetate/lactate to control Salmonella, E. coli O157:H7, Listeria monocytogenes.
Seafood: Raw shrimp, surimi, fish fillets, smoked salmon, and crab meat.
Dairy products: Processed cheese slices, cheese spreads, cottage cheese, cream cheese, sour cream dips, yogurt, ice cream mix.
Bakery: Tortillas, flatbreads, pita, cakes, pastries, cream-filled donuts.
Sauces and dressings: Mayonnaise, salad dressings (emulsified), marinades, salsas, and dips.
Beverages: Ready-to-drink (RTD) coffees and teas, protein shakes, flavored milks, fruit smoothies.
Pet food and animal feed: Wet and semi-moist formulations.
Cosmetics and personal care: Mouthwash, toothpaste, contact lens cleaning solutions, skin creams, shampoos (as preservative and mild biocide).
Medical: Catheter lock solutions, wound dressings, topical antiseptic.
Description:
 Ethyl lauroyl arginate (LAE, E243) is a cationic surfactant and broad-spectrum antimicrobial agent derived from natural sources: lauric acid (from coconut oil or palm kernel oil) and L-arginine (an essential amino acid produced by fermentation). The molecule features an ethyl ester linkage connecting lauric acid to the α-amino group of arginine, while the guanidinium group of arginine remains intact. This unique structure imparts both hydrophilic (guanidinium, positively charged) and lipophilic (lauryl chain) properties, allowing LAE to insert into microbial cell membranes. The mechanism of action involves electrostatic attraction between the positively charged guanidinium group and negatively charged microbial membrane components (phospholipids, lipopolysaccharides, teichoic acids). Upon binding, LAE disrupts membrane integrity, causing rapid leakage of intracellular ions, ATP, and small metabolites, followed by dissipation of the proton motive force and cell death. Unlike some surfactants (e.g., quaternary ammonium compounds), LAE does not cause bacterial resistance development due to its multi-target action (membrane disruption, interference with DNA replication, and inhibition of key enzymes). LAE is extremely effective at low concentrations: minimum inhibitory concentrations (MICs) range from 2–32 ppm for Gram-positive bacteria (Listeria monocytogenes, Staphylococcus aureus, Bacillus cereus) and 4–64 ppm for Gram-negative bacteria (E. coli O157:H7, Salmonella enterica, Campylobacter jejuni, Pseudomonas aeruginosa). It is also fungicidal against yeasts (Candida, Zygosaccharomyces) and molds (Aspergillus, Penicillium) at 5–50 ppm. One of the most remarkable properties of LAE is its rapid hydrolysis in the human body: after ingestion, it is cleaved by esterases and amidases into lauric acid (a common dietary fatty acid) and L-arginine (an essential amino acid), plus ethanol (at negligible levels). Therefore, LAE is completely nontoxic and not absorbed as the parent compound. The ADI established by JECFA is 0–10 mg/kg bw/day (very safe). The US FDA approved LAE as Generally Recognized as Safe (GRAS) for use as an antimicrobial preservative in various meat, poultry, seafood, dairy, and beverage products (GRN No. 296, 316, 323). LAE does not significantly alter taste, odor, color, or texture at effective concentrations (50–200 ppm). Unlike nitrites (E249-E252), LAE does not form carcinogenic nitrosamines. Unlike sorbic acid (E200), it is effective in neutral pH foods (pH 5–7) and in high-fat systems. However, LAE can be inactivated by anionic ingredients (e.g., carrageenan, alginate, anionic emulsifiers, high concentrations of lecithin or caseinate) due to electrostatic neutralization and precipitation. Therefore, formulation compatibility studies are essential. In meat products, LAE synergizes with sodium diacetate, potassium lactate, and sodium citrate to control Listeria monocytogenes on ready-to-eat meats. In tortillas, LAE extends mold-free shelf life from 14 days to 45 days at room temperature. Its positive environmental profile (biodegradable, low aquatic toxicity) makes it a sustainable alternative to synthetic preservatives. The commercial product is typically sold as the hydrochloride salt (ethyl lauroyl arginate HCl, e.g., Apetit™, Mirenat™, LAE powder) at 95% purity. Due to its cationic nature, it is incompatible with anionic thickeners like xanthan gum at high concentrations (above 0.3%). Despite this limitation, LAE represents one of the most significant advances in food preservation in the past two decades, bridging the gap between "clean label" consumer expectations and industrial microbial safety requirements.

SAFETY INFORMATION ABOUT ETHYL LAUROYL ARGINATE

First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product