3397-65-7

Usage

Uses

Used in Chemical Industry:
N-Lauroyl-L-glutamic acid is used as a precursor in the synthesis of various chemical compounds for different purposes, such as pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows it to be a key building block in the development of new molecules with specific properties.
Used in Environmental Applications:
N-Lauroyl-L-glutamic acid is used as a degrading agent for formaldehyde. Formaldehyde is a common indoor air pollutant that can cause health issues, and the use of N-Lauroyl-L-glutamic acid helps in breaking down this harmful compound, improving air quality and reducing exposure to its harmful effects.
Used in Pharmaceutical Industry:
N-Lauroyl-L-glutamic acid is used as a carrier molecule in drug delivery systems. Its amphiphilic nature allows it to encapsulate and transport hydrophobic drugs, improving their solubility, bioavailability, and overall therapeutic efficacy.
Used in Cosmetics Industry:
N-Lauroyl-L-glutamic acid is used as an emulsifier and surfactant in cosmetic formulations. Its ability to interact with both water and oil makes it an effective ingredient in creating stable emulsions, which are essential for various cosmetic products such as creams, lotions, and shampoos.

InChI:InChI=1/C17H31NO5/c1-2-3-4-5-6-7-8-9-10-11-15(19)18-14(17(22)23)12-13-16(20)21/h14H,2-13H2,1H3,(H,18,19)(H,20,21)(H,22,23)

Upstream product

• 112-16-3 n-dodecanoyl chloride 
• 56-86-0 L-glutamic acid 
• 118429-76-8 N^α-lauryl-L-glutamic acid dibenzyl ester 
• 143-07-7 lauric acid 
• 142-47-2 monosodium L-glutamate 
• 2791-84-6 L-glutamic acid dibenzyl ester 4-toluenesulfonate 
• 7783-05-3 disulfuric acid 
• 113493-05-3 C₂₁H₃₉NO₅ 
• 111-82-0 methyl n-dodecanoate 
• 142-47-2 glutamic acid sodium salt 

Downstream Products

• 63663-21-8 N-lauroyl-L-glutamic acid N,N'-(dibutylamide) 
• 143-07-7 lauric acid 
• 56-86-0 L-glutamic acid 

Relevant academic research and scientific papers

pH-sensitive wormlike micelle and hydrogel formation by acylglutamic acid-alkylamine complex

pH-sensitive viscoelastic fluids were obtained through the formation of wormlike micelles and hydrogels. These assemblies result from the 1:1 stoichiometric complex formation of acylglutamic acid (CnGlu) with tertiary alkylamine. The pH-sensitive nature reflects a change in the charge density around the CnGlu headgroups, controlling the curvature of the molecular assemblies. The longer chainCnGlu analogues yield the hydrogel in a narrow pH region. This study proposes a unique way to obtain stimulus-responsive viscoelastic fluids by means of gemini-like amphiphiles.

Preparation method and application of amido carboxylic acid compound

The invention discloses a preparation method and application of an amido carboxylic acid compound. The preparation method comprises the step of subjecting organic carboxylic acid with a structure represented by a formula (I) shown in the description and an amino acid compound with a structure represented by a formula (II) shown in the description to a grinding reaction in the presence of a coupling reagent, thereby preparing the amido carboxylic acid compound with a structure represented by a formula (III) shown in the description. The product prepared by the method is high in yield, is energy-saving and environmentally friendly and does not need aftertreatment. According to the application, the amido carboxylic acid compound is applied to mineral flotation separation as a collector, and the collector has relatively high collection capability and relatively good selectivity and is particularly applicable to the flotation separation of minerals such as wolframite, scheelite, rare earthminerals, cassiterite, ilmenite, bauxite, manganese oxide ores, phosphorite and fluorite.

Manufacturing technology for fatty acyl amino acid

The invention discloses a manufacturing technology for fatty acyl group amino acid. The invention is characterized in that fatty acid methyl ester and amino sodium are taken as raw materials, a one-step synthesis method is adopted for synthesizing N-fatty acyl amino acid sodium surfactant under the effect of a metallic oxide catalyst and the mole ratio of the raw materials fatty acid methyl ester to sodium amino acid is (1.2-1.8):(0.7-1). The raw material proportion is proper, the by-product is almost not generated, the product synthetic ratio is as high as 87% or above, the purity is high, the problems of a large amount of to-be-treated waste acid, complex operation technology, high raw material PC13 irritation, and the like, of the traditional acyl chloride process are overcome and the technology accords with the green chemical principle. The dosage of the catalyst is reasonable; the catalyst is utilized, so that the production efficiency is greatly increased in the preparation process, the production flow is shortened and the product quality is increased; the excellent product even can be directly used as a raw material in pharmacy industry.

Using the ionic liquid amino or N-acylated peptide dialkylsulfosuccinic N of manufacturing method

PROBLEM TO BE SOLVED: To provide a method for synthesizing N-acylamino acid or N-acylpeptide without using fatty acid chloride.SOLUTION: The method for producing N-acylamino acid or N-acylpeptide comprises a step of reacting ionic liquefied amino acid or peptide (A) with a fatty acid or ester thereof (B) under such a condition that a molar ratio of (A):(B) is 1:10 to 10:1.

Regulation of the chiral twist and supramolecular chirality in co-assemblies of amphiphilic L-glutamic acid with bipyridines

A series of amphiphilic L-glutamic acid derivatives with various saturated alkyl chains has been designed and their co-assembly with 4,4′-bipyridine in aqueous media has been investigated. While the individual amphiphiles formed hydrogels with water and self-assembled into fine fiber networks, the addition of 4,4′-bipyridine caused significant changes in the co-assembled nanostructures such that twisted chiral ribbons were formed. In these supramolecular systems, either fine structural changes or adjustment of the stoichiometric ratio of the two components had crucial effects on the formation of the chiral twists. Based on detailed investigations by SEM and XRD analyses, FTIR, CD, and UV/Vis spectroscopies, and molecular simulation, it is considered that a delicate synergistic balance between π-π stacking, hydrophobic, and chiral interactions is responsible for the formation of the chiral twists. An interesting sandwich structure, in which an excess of 4,4′-bipyridine is inserted into the space of primary cages constructed from the amphiphile and 4,4′-bipyridine, is proposed. Remarkably, the handedness of these chiral twists is related not only to the chiral center of the glutamic unit, but also the chain length of the alkyl tails. This work provides a deeper understanding of the formation mechanism of chiral twists, and exemplifies a feasible shortcut to the rational design of chiral structures from basic molecular structures to supramolecular systems. Twisted nanostructures: A chiral twist has been obtained through the co-assembly of single-chain L-glutamic acids with bipyridines (see picture). The sandwiching of additional 4,4′-bipyridine within the cage formed by the amphiphile and the bipyridine caused the chiral twist. The dimensions and chirality of the twist could be regulated by adjusting the alkyl chain length of the amphiphile. Copyright

Inflammation Inhibitor Comprising Zinc Salt of Acylamino Acid

An inflammation inhibitor for the skin is provided containing a zinc salt of an acylamino acid and further, a cosmetic containing the inflammation inhibitor.

Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus

A high throughput screen against POLO-like kinase 1 (Plk1), an anti-cancer target, identified an active extract from the fungus Arachniotus punctatus. Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) with IC50 values of 13 and 118 μM, respectively. A 12′-hydroxy analog of gymnastatin N, 3, was also isolated as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic acid moieties might be responsible for its bioactivity. Graphical Abstract.

Enzymatic synthesis of N-acyl-L-amino acids in a glycerol-water system using acylase I from pig kidney

N-Medium-and long-chain acyl-L-amino acids were enzymatically synthesized from the corresponding L-amino acids and fatty acids using a reverse hydrolysis. Enzymes that are suitable for the synthetic reaction of N-acyl-L-amino acids were screened on the basis of hydrolytic activity toward N-lauroyl-L-glutamic acid as an indicator. Acylase I from pig kidney (EC 3.5.1.14) showed the highest N-acyl-L-amino acid hydrolytic activity among 57 commercially available enzymes tested. Acylase I effectively catalyzed the synthesis of N-lauroyl-L-amino acids except for N-lauroyl-L-proline and N-lauroyl-L-tyrosine in a glycerol-water system. Under the optimized reaction conditions, N-lauroyl-L-arginine and N-lauroyl-L-glutamic acid were obtained in conversions of 82 and 44%, respectively. The equilibrium constants calculated from the conversion obtained were 5.6, 15.4, 18.0, and 39.4 for the syntheses of N-lauroyl-L-glutamic acid, Nα-lauroyl-L-lysine, N-lauroyl-L-glutamine, and N-lauroyl-L-methionine, respectively. N-Acyl-L-arginines with myristic acid and palmitic acid as the fatty acid were also synthesized using acylase I.

Process for producing N-long-chain acyl acidic amino acids or salts thereof

N-long-chain acyl acidic amino acids or salts thereof are prepared by condensing an acidic amino acid or a salt thereof and a C8 -C22 long-chain fatty acid chloride in an aqueous solvent with stirring at a stirring power of not less than 0.2 kW/m3 while keeping the pH in the range of 10-13.

Cosmetic composition

A composition suitable for topical application to mammalian skin and hair for inducing, maintaining or increasing hair growth comprises a hair growth promoter chosen from glutamine derivatives and salts thereof. The composition preferably also comprises an activity enhancer which may be chosen from hair growth stimulants, penetration enhancers and cationic polymers.