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CAS Number : 48076-74-0
EC Number : 434-630-6
ChemSpider : 163603
PubChem CID : 188214
Chemical formula : C20H40N4O3
Molar mass : 384.565 g·mol−1
IUPAC name :
Ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate
Other names :
-Ethyl N(alpha)-lauroyl-L-arginate
-Lauric arginate ethyl ester
Ethyl lauroyl arginate (LAE) is a food preservative more commonly known as E243.
Ethyl lauroyl arginate has chemical formula C20H40N4O3 and is a drug for dermatological disorders.
Periodontal diseases of Ethyl lauroyl arginate
Ethyl lauroyl arginate has potential in treating gingivitis, and the more advanced periodontitis.
In a study comparing ethyl lauroyl arginate in 0.147% mouthwash to chlorhexidine (CHX) 0.12% as an adjunctive therapy in the non-surgical treatment of periodontitis, the results showed there were no treatment-related adverse events.
Total bacterial count and the specific pathogens were reduced at 4 weeks and 3 months by both mouthwashes with no statistical differences between them at neither periods of time.
Ethyl lauroyl arginate was concluded that 0.147% LAE-containing mouthwash could be an alternative to the use of 0.12% CHX in the non-surgical therapy of periodontitis considering the similar clinical effects, more stable microbiological improvement and absence of adverse effects.
Ethyl lauroyl arginate is sold as the main active ingredient in Listerine Advanced Defence Gum Treatment and as one of the active ingredients in GUM Activital Mouthwash.
Ethyl lauroyl arginate is used as preservative.
Ethyl lauroyl arginate which is a cationic surfactant has a wide spectrum of activity against Gram positive and negative bacteria, yeasts and moulds.
Ethyl lauroyl arginate acts on cell membranesand the cytoplasm, and inhibits the growth of populations but in no case is celllysis observed under the conditions studied.
Ethyl lauroyl arginate can be used in a wide range of foods.
Ethyl lauroyl arginate is used as a food antimicrobial in the sanitation of preserved foods.
Ethyl lauroyl arginate is also used in cosmetics as a preservative.
The use of ethyl lauroyl arginate (LAE) as an antimicrobial and food preservative is currently approved by the Food and Drug Administration (FDA) and the European Food Safety Agency (EFSA), respectively.
Due to this fact, in recent years, there has been a great focus on the possible application of this compound to food systems.
In this chapter, although an overview on Ethyl lauroyl arginate synthesis, properties, stability, metabolism, and toxicity is provided, a special emphasis is given to this compound’s antimicrobial activity and mode of action, as well as its application in food systems.
Ethyl lauroyl arginate is a fairly stable compound with low reactivity that is synthesized through esterification and condensation steps.
The vast amount of in vitro and in vivo toxicological studies demonstrates that Ethyl lauroyl arginate has low toxicity, possibly due to the fact that this compound is readily hydrolyzed by chemical and metabolic pathways.
Ethyl lauroyl arginate is effective as a food preservative, due to its strong antimicrobial activity against a wide range of microorganisms, including molds, yeasts, gram-positive, and gram-negative bacteria.
Ethyl lauroyl arginate is the active ingredient in the commercial product, LAE.
In the crude technical product the aqueous paste contains 74-84% Ethyl lauroyl arginate .
Ethyl lauroyl arginate is the dehydrated crude product containing 85-95% Ethyl lauroyl arginate.
Ethyl lauroyl arginate is a food-grade cationic surfactant with antimicrobial properties that is derived from the natural building blocks lauric acid and L-arginine.
Ethyl lauroyl arginate inhibits the proliferation of microorganisms such as bacteria, fungi and yeasts by disturbing their cell membrane potential, altering cell permeability and thereby inducing the loss of cell viability.
Ethyl lauroyl arginate (LAE) is an amino acid-based cationic surfactant with low toxicity and antimicrobial activity.
Ethyl lauroyl arginate is widely used as a food preservative and component for food packaging.
When stored, Ethyl lauroyl arginate 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 Ethyl lauroyl arginate.
Ethyl lauroyl arginate can be used by as a preservative in personal care products (creams, lotions, body milks and hair conditioners) and as an active compound in soaps, antidandruff shampoos, deodorants and oral care products.
Additionally, Ethyl lauroyl arginate can provide smoothness to skin and hair because of its cationic nature.
Ethyl lauroyl arginate has a proven high antimicrobial efficacy in cosmetic products.
Furthermore, Ethyl lauroyl arginate has unique advantages over most of the currently approved cosmetic preservatives because Ethyl lauroyl arginate is an environmentally friendly product being certificated for sustainable production process according to the twelve principles of Green Chemistry.
Ethyl lauroyl arginate(Lauric Arginine Ethyl for labeling purposes under FDA approval ) is a derivative of lauric acid, Larginine and ethanol.
The main characteristics of the molecule are a wide range of antimicrobial properties derived from its surfactant chemical structure that additionally yields certain tensioactive properties.
Ethyl lauroyl arginate shows chemical stability at pH range between 3 to 7 and maintains its antimicrobial activity in this interval，this offers a significant advantage compared to other products currently available in the market.
Extraction of Ethyl lauroyl arginate:
This natural preservative is obtained from the combination of the natural amino acid L-arginine and lauric acid from coconut oil.
Benefits of Ethyl lauroyl arginate :
This salt has high, broad spectrum antimicrobial activity and is an excellent ingredient for use in natural, aluminum-free deodorants.
Ethyl lauroyl arginate is a chemical compound that inhibits the growth of bacteria.
Ethyl lauroyl arginate is a quaternary ammonium salt that is stable to heat and other physical stress.
Ethyl lauroyl arginate has been shown to be active against Listeria monocytogenes, Salmonella enterica, Escherichia coli and Enterobacter aerogenes.
Ethyl lauroyl arginate may also have antimicrobial activity against other organisms, such as fungi and viruses.
Ethyl lauroyl arginate has been shown to cause cell lysis by disrupting the membrane of cells and interfering with the synthesis of proteins required for cell division.
This agent also has a sweet taste, which can be used in food products as an artificial sweetener.
Ethyl Lauroyl Arginate (LAE) is a cationic tensoactive compound, soluble in water, with a wide activity spectrum against moulds and bacteria.
Ethyl lauroyl arginate has been incorporated as antimicrobial agent into packaging materials for food contact and these materials require to comply with the specific migration criteria.
Ethyl lauroyl arginate is typically found as a white powder.
This can present some technical difficulties in food processing because it often needs to be applied evenly and in low doses.
To make Ethyl lauroyl arginate easier to work with, liquid forms can be created by dissolving it in food grade solvents such as Glycerol.
Ethyl lauroyl arginate is classified as a cationic surfactant.
A surfactant is basically a soap molecule where one end is attracted to fats and oils while the other end is attracted to water.
The end of the molecule that is attracted to water contains a positively charged ion (a cation).
As a preservative, Ethyl lauroyl arginate acts to break down the membranes in bacteria, yeast, or mould cells.
Once the membranes have been broken, the cells die.
Applications of Ethyl Lauroyl Arginate
-water-based non-alcoholic beverages,
-soups,
-cheese products,
-sauces and dips,
-ketchup,
-pie fillings, and
-meat, poultry and fish products
Ethyl Lauroyl Arginate (Lauric Arginine Ethyl for labeling purposes under FDA approval ) is a derivative of lauric acid, L-arginine and ethanol.
The main characteristics of the molecule are a wide range of antimicrobial properties derived from its surfactant chemical structure that additionally yields certain tensioactive properties.
This compound is a white hygroscopic solid , dispersible in water up to 247 g/kg with a melting point at 50℃ to 58℃.
Its partition coefficient between water and oil(soy, sunflower, olive) is higher than 10 which means that the molecule is mainly located in the water fraction, which is more susceptible to microbial contamination.
This property gives Ethyl Lauroyl Arginate an advantage over other preservatives with different chemical structure intended for the same applications.
First-aid measures of Ethyl Lauroyl Arginate
Inhalation:
Remove to fresh air.
Move to fresh air.
Call a physician if symptoms develop or persist.
Skin contact :
Rinse skin with water/shower.
Get medical attention if irritation develops and persists.
Eye contact :
Rinse cautiously with water for several minutes.
Remove contact lenses, if present and easy to do.
Continue rinsing.
Call a physician or poison control center immediately.
Ingestion :
Rinse mouth.
Get medical advice/attention if you feel unwell.
If ingestion of a large amount does occur, call a poison control center immediately.
Substance identity
EC / List no.: 434-630-6
CAS no.: 48076-74-0
Mol. formula: C20H40N4O3
Hazard classification & labelling of Ethyl lauroyl arginate
Danger! According to the harmonised classification and labelling (ATP01) approved by the European Union, this substance is very toxic to aquatic life and causes serious eye damage.
Additionally, the classification provided by companies to ECHA in REACH registrations identifies that this substance is harmful to aquatic life with long lasting effects.
About Ethyl lauroyl arginate
Ethyl lauroyl arginate is registered under the REACH Regulation and is manufactured in and / or imported to the European Economic Area, at ≥ 10 to < 100 tonnes per annum.
Ethyl lauroyl arginate is used by consumers, by professional workers (widespread uses), in formulation or re-packing, at industrial sites and in manufacturing.
Consumer Uses of Ethyl lauroyl arginate
Ethyl lauroyl arginate is used in the following products: cosmetics and personal care products.
Other release to the environment of Ethyl lauroyl arginate is likely to occur from: indoor use as processing aid.
Article service life of Ethyl lauroyl arginate
ECHA has no public registered data on the routes by which Ethyl lauroyl arginate is most likely to be released to the environment.
ECHA has no public registered data indicating whether or into which articles the substance might have been processed.
Widespread uses by professional workers of Ethyl lauroyl arginate
Ethyl lauroyl arginate is used in the following products: cosmetics and personal care products.
ECHA has no public registered data on the types of manufacture using this substance.
Other release to the environment of Ethyl lauroyl arginate is likely to occur from: indoor use as processing aid.
Formulation or re-packing of Ethyl lauroyl arginate
Ethyl lauroyl arginate is used in the following products: cosmetics and personal care products.
Release to the environment of Ethyl lauroyl arginate can occur from industrial use: formulation of mixtures.
Uses at industrial sites of Ethyl lauroyl arginate
Ethyl lauroyl arginate is used in the following products: fuels and extraction agents.
ECHA has no public registered data on the types of manufacture using Ethyl lauroyl arginate.
Release to the environment of Ethyl lauroyl arginate can occur from industrial use: in processing aids at industrial sites.
Manufacture of Ethyl lauroyl arginate
Release to the environment of Ethyl lauroyl arginate can occur from industrial use: manufacturing of the substance.
Synonyms:
N(alpha)-Lauroylarginine ethyl ester
48076-74-0
ethyl lauroyl arginate
UNII-E0K8J7A41B
E0K8J7A41B
N-(alpha)-Lae
Nacaee
N-(alpha)-Cae
N(alpha)-Cocylarginine ethyl ester
N(alpha)-Cocoylarginine ethyl ester
N(alpha)-Lauroyl-arginine ethyl ester
L-EthylLauroylArginate
N(alpha)-Cocoyl-L-arginine ethyl ester
L-Ethyl Lauroyl Arginate
lauroyl arginine ethyl ester
SCHEMBL2409308
DTXSID60893076
AMY28678
ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate
N-(alpha)-Lauroyl-L-arginine ethyl ester, DL-pyroglutamic acid salt
N alpha-Lauroyl-L-arginine ethyl ester
L-Arginine, N2-(1-oxododecyl)-, ethyl ester
Q27276710
Cytoguard LA
Ethyl lauroyl arginate HCl
Ethyl lauroyl arginate hydrochloride
ethyl N2-dodecanoyl-.sc.l.sc.-argininate hydrochloride
Ethyl N2-dodecanoyl-L-argininate hydrochloride
ethyl N2-dodecanoyl-l-argininate hydrochloride
Ethyl-N-alpha-dodecanoyl-L-arginate hydrochloride
Cosmetic Products Regulation, Annex III - Restricted Substances, Cosmetic Products Regulation, Annex V - Allowed Preservatives
L-Arginine, N2-(1-oxododecyl)-, ethyl ester, hydrochloride (1:1)
L-Arginine, N2-(1-oxododecyl)-, ethyl ester, monohydrochloride
L.A.E.
LAE
chlorowodorek etylo N2-dodekanoylo-L-argininianu (pl)
clorhidrato de N2-dodecanoil-L-argininato de etilo (es)
cloridrato de N2-dodecanoil-L-argininato de etilo (pt)
ethyl-N2-dodecanoyl-L-argininaat hydrochloride (nl)
ethyl-N2-dodecanoyl-L-argininathydrochlorid (da)
Ethyl-N2-dodecanoyl-L-argininhydrochlorid (de)
ethyl-N2-dodekanoyl-L-argininát-hydrochlorid (cs)
etil <I>N</I>2-dodekanoil-L-argininat hidroklorid (hr)
etil N2-dodekanoil-L-argininat hidroklorid (sl)
etil N2-dodekanoil-L-argininát hidroklorid (hu)
etil-N2-dodekanoil-L-argininato hidrochloridas (lt)
etil-N2-dodekanoil-L-arginināta hidrohlorīds (lv)
etyl-N2-dodecanoyl-L-argininathydroklorid (no)
etyl-N2-dodekanoyl-L-arginat hydroklorid (sv)
etyyli-N2-dodekanoyyli-L-argininaattihydrokloridi (fi)
etüül-N2-dodekanoüül-L-argininaatvesinikkloriid (et)
hydrochlorid O-etyl-N2-dodekanoyl-L-argininátu (sk)
idrocloruro di N2-dodecanoil-L-argininato di etile (it)
idroklorur ta' N2-dodekanojl-l-arċininat (mt)
N2-dodecanoil-L-argininat de etil hidroclorură (ro)
N2-dodécanoyl-l-argininate d'éthyle, chlorhydrate (fr)
υδροχλωρικό άλας του N2-δωδεκανοϋλ-L-αργινινικού αιθυλίου (el)
етил N2-додеканоил-L-аргининат хидрохлорид (bg)
L-Arginine, N2-(1-oxododecyl)-, ethyl ester, hydrochloride (1:1)
ethyl (2S)-5-(diaminomethylideneamino)-2-(dodecanoylamino)pentanoate;hydrochloride
ethyl (2S)-5-carbamimidamido-2-dodecanamidopentanoate hydrochloride
ethyl N2-dodecanoyl-L-argininate hydrochloride
ethyl N2-dodecanoyl-l-argininate hydrochloride
L.A.E.
L.A.E.
60372-77-2
92071-28-8
607-652-00-0
