60372-77-2

Basic information

• Product Name: ETHYL LAUROYL ARGINATE HCL
• Synonyms: ETHYL LAUROYL ARGINATE HCL;N-ALPHA-LAUROYL-L-ARGININEETHYLESTERMONOHYDROCHLORIDE;ETHYL-N-ALPHA-LAUROYL-L-ARGINATEHYDROCHLORIDE;ETHYLLAUROYLARGINATEHYDROCHLORIDE;Aminat G;CytoGuard LA;Ethyl N-lauroyl-L-arginate hydrochloride;Mirenat CF
• CAS NO: 60372-77-2
• Molecular Formula: C₂₀H₄₀N₄O₃*ClH
• Molecular Weight: 421.01754
• Mol File: 60372-77-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.11[at 20℃]
• Vapor Pressure: 0.001Pa at 25℃
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: 247g/L at 20℃
• CAS DataBase Reference: ETHYL LAUROYL ARGINATE HCL(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL LAUROYL ARGINATE HCL(60372-77-2)
• EPA Substance Registry System: ETHYL LAUROYL ARGINATE HCL(60372-77-2)

Safety Data

• RIDADR: UN 3077 9 / PGIII
• Hazardous Substances Data: 60372-77-2(Hazardous Substances Data)

Usage

Uses

Ethyl Lauroyl Arginate Hydrochloride is used as a food antimicrobial in the sanitation of preserved foods. It is also used in cosmetics as a preservative.

Chemical Properties

off-white to white crystalline powder

Flammability and Explosibility

Nonflammable

Synthetic route

n-dodecanoyl chloride (112-16-3) + L‐arginine ethyl ester hydrochloride → Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2)

Conditions	Yield
With sodium hydroxide In water; ethyl acetate at 8 - 30℃; pH=7.3 - 7.5; Product distribution / selectivity;	98.1%
With sodium hydrogencarbonate; sodium carbonate In water; ethyl acetate at 20℃; for 3h; Green chemistry;	96%
Stage #1: n-dodecanoyl chloride; L‐arginine ethyl ester hydrochloride With triethylamine In tetrahydrofuran at 15 - 40℃; Stage #2: With hydrogenchloride In water at 10℃; Concentration; Solvent; Temperature; Time; Reagent/catalyst;	94.06%

Nα-lauroyl-arginine ethyl ester → Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2)

Conditions	Yield
With hydrogenchloride for 0.5h; Time;	96.4%

lauric acid (143-07-7) + arginine ethyl ester hydrochloride → Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2)

Conditions	Yield
Stage #1: lauric acid With 1,1'-carbonyldiimidazole In ethyl acetate at 30℃; for 1h; Large scale; Green chemistry; Stage #2: arginine ethyl ester hydrochloride With triethylamine In ethyl acetate at 30℃; for 2h; Temperature; Large scale; Green chemistry;	93%

lauric acid (143-07-7) + L-arginine ethyl ester hydrochloride → Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2)

Conditions	Yield
With benzotriazol-1-ol; diisopropyl-carbodiimide In isopropyl alcohol at 45℃; for 30h; Reagent/catalyst; Solvent; Temperature; Green chemistry;	8.76 g

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + sodium acetate (127-09-3) → Nα-lauroyl-L-arginine ethyl ester acetate (92071-96-0)

Conditions	Yield
In water at 75 - 80℃; for 6h; Product distribution / selectivity;	98.5%

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + Sodium laurate (629-25-4) → Nα-lauroyl-L-arginine ethyl ester laurate (1193347-26-0)

Conditions	Yield
In water at 80 - 85℃; for 0.5h;	96.5%

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + glycolic Acid (79-14-1) → lauroyl arginine ethyl ester glycolate

Conditions	Yield
Stage #1: Nα-lauroyl-L-arginine ethyl ester monohydrochloride With pyridine In acetic acid butyl ester at 60℃; for 1h; Stage #2: glycolic Acid at 60℃; for 3h; Concentration; Reagent/catalyst; Solvent; Temperature;	95.2%

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + oxalic acid (144-62-7) → C20H40N4O3*C2H2O4

Conditions	Yield
With sodium hydroxide In methanol; water at 90℃; for 2h;	5 g

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + sodium carbonate (497-19-8) → C20H40N4O3*CHO3(1-)

Conditions	Yield
With sodium hydroxide In water at 90℃; for 2h;	4 g

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + sodium nicotinate (54-86-4) → C20H40N4O3*C6H5NO2

Conditions	Yield
In water at 90℃; for 2h;	7.6 g

Nα-lauroyl-L-arginine ethyl ester monohydrochloride (60372-77-2) + tartaric acid (87-69-4) → C20H40N4O3*C4H6O6

Conditions	Yield
With sodium hydroxide In methanol; water at 90℃; for 2h;	6.3 g

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 33171-13-0 L‐arginine ethyl ester hydrochloride 
• 143-07-7 lauric acid 
• 33171-13-0 L-arginine ethyl ester hydrochloride 
• 48076-74-0 N^α-lauroyl-arginine ethyl ester 
• 33171-13-0 arginine ethyl ester hydrochloride 

Relevant articles and documents

Preparation process of ethyl lauroyl arginate hydrochloride

The invention discloses a preparation process of ethyl lauroyl arginate hydrochloride. The method comprises the following steps: 1) adding L-arginine hydrochloride into absolute ethyl alcohol, performing stirring, and dropwise adding trimethylchlorosilane to obtain L-arginine ethyl ester hydrochloride; 2) dissolving the L-arginine ethyl ester hydrochloride in absolute ethyl alcohol, and dropwise adding triethylamine and lauroyl chloride respectively to obtain an ethyl lauroyl arginate crude product; 3) mixing the ethyl lauroyl arginate crude product with deionized water and an organic solvent, removing a water phase, performing washing with saturated sodium chloride to obtain a solvent phase, and performing drying by distillation to obtain L-ethyl lauroyl arginate hydrochloride; and 4), stirring the L-ethyl lauroyl arginate hydrochloride with petroleum ether, and performing standing crystallization and suction filtration to obtain ethyl lauroyl arginate hydrochloride. The trimethylsilane is used in the preparation technological process of the ethyl lauroyl arginate hydrochloride, so that the reaction condition is mild, operation is easy, green and environment-friendly effects are achieved, the yield reaches 99% or above, and the product purity reaches 99% or above.

Preparation technology of ethyl lauroyl arginate hydrochloride

The invention provides a preparation technology of ethyl lauroyl arginate hydrochloride. The product is prepared by adopting a process of directly carrying out an esterification and acylation two-stepseries reaction and salifying by using HCl gas for post-treatment. The yield of the preparation technology reaches 95.8% or above, and the purity of the product reaches 98% or above. Compared with the prior art, the technology of the invention has the advantages of simplicity and easiness in operation, no production of wastewater, low cost, high raw material utilization rate, high reaction efficiency and the like.

Method for preparing ethyl lauroyl arginate hydrochloride

The invention relates to a method for preparing ethyl lauroyl arginate hydrochloride. The method comprises the steps of dissolving L-ethyl arginate hydrochloride, lauric acid, a carbodiimide condensing agent and a catalyst in short-chain alcohol, carrying out a reaction for 4 to 48 hours at the temperature of 20 DEG C to 60 DEG C, subjecting a solution to depressurization to remove a solvent so asto obtain white solids, dissolving the white solids with water, carrying out suction filtration so as to obtain filtrate, subjecting the obtained filtrate to salting-out with an inorganic salt so asto prepare a white lumpy solid crude product, leaching the crude product with cold water for three times, and then, carrying out drying, thereby obtaining the ethyl lauroyl arginate hydrochloride. Themethod has the advantages that the method is pollution-free, the cost is low, the toxicity is low, and the purity of the product can reach 95% or more.