8038-89-9

Usage

Uses

Used in Industrial Applications:
N-(2-hydroxyethyl)octadecanamide is used as a slip agent and lubricant for improving the processing and performance of materials in industries such as plastics, rubbers, and textiles.
Used in Cosmetics and Personal Care Products:
N-(2-hydroxyethyl)octadecanamide is used as an emollient and skin conditioning agent to provide moisturization and improve the texture and appearance of the skin.
Used in Therapeutic Applications:
N-(2-hydroxyethyl)octadecanamide is used for its potential anti-inflammatory and anti-itch properties, making it a candidate for the development of treatments for various skin conditions and inflammatory disorders.
Used in Neurological Research:
N-(2-hydroxyethyl)octadecanamide is studied for its potential neuroprotective and antioxidant effects, which may contribute to the development of therapies for neurological disorders and conditions.

Upstream product

• 10287-60-2 O-stearoylethanolamine 
• 111-61-5 stearic acid ethyl ester 
• 141-43-5 ethanolamine 
• 57-11-4 stearic acid 
• 112-76-5 Stearoyl chloride 
• 14464-32-5 stearic acid N-hydroxysuccinimide ester 
• 111-63-7 vinyl stearate 
• 112-61-8 Methyl stearate 
• 124-26-5 stearamide 

Downstream Products

• 31383-80-9 Phthalic acid mono-(2-octadecanoylamino-ethyl) ester 
• 1613511-63-9 N-octadecanoylethanolamine-o-(phtaloyl(triethylene glycol)) 
• 6333-54-6 N-stearoylglycine 
• 82755-92-8 2-octadecanamidoethylphosphocholine 

Relevant academic research and scientific papers

Different roles for the acyl chain and the amine leaving group in the substrate selectivity of N-Acylethanolamine acid amidase

N-acylethanolamine acid amidase (NAAA) is an N-terminal nucleophile (Ntn) hydrolase that catalyses the intracellular deactivation of the endogenous analgesic and anti-inflammatory agent palmitoylethanolamide (PEA). NAAA inhibitors counteract this process and exert marked therapeutic effects in animal models of pain, inflammation and neurodegeneration. While it is known that NAAA preferentially hydrolyses saturated fatty acid ethanolamides (FAEs), a detailed profile of the relationship between catalytic efficiency and fatty acid-chain length is still lacking. In this report, we combined enzymatic and molecular modelling approaches to determine the effects of acyl chain and polar head modifications on substrate recognition and hydrolysis by NAAA. The results show that, in both saturated and monounsaturated FAEs, the catalytic efficiency is strictly dependent upon fatty acyl chain length, whereas there is a wider tolerance for modifications of the polar heads. This relationship reflects the relative stability of enzyme-substrate complexes in molecular dynamics simulations.

An Aldehyde Responsive, Cleavable Linker for Glucose Responsive Insulins

A glucose responsive insulin (GRI) that responds to changes in blood glucose concentrations has remained an elusive goal. Here we describe the development of glucose cleavable linkers based on hydrazone and thiazolidine structures. We developed linkers with low levels of spontaneous hydrolysis but increased level of hydrolysis with rising concentrations of glucose, which demonstrated their glucose responsiveness in vitro. Lipidated hydrazones and thiazolidines were conjugated to the LysB29 side-chain of HI by pH-controlled acylations providing GRIs with glucose responsiveness confirmed in vitro for thiazolidines. Clamp studies showed increased glucose infusion at hyperglycemic conditions for one GRI indicative of a true glucose response. The glucose responsive cleavable linker in these GRIs allow changes in glucose levels to drive the release of active insulin from a circulating depot. We have demonstrated an unprecedented, chemically responsive linker concept for biopharmaceuticals.

N-stearoylethanolamine — a new inhibitor of the hepatitis c virus reproduction

Aim. The study of the effect of endogenous cannabimimetic compound-N-stearoylethanolamine (NSE) on the hepatitis C virus (HCV) reproduction. Methods. The model of the surrogate HCV is a bovine diarrhea virus; cell culture model is cells transfected with cDNA of the human HCV and molecular docking has been used. Results. In vitro studies showed that NSE effectively inhibited the reproduction of a surrogate HCV in both MDBK cells and transfected Jurkat cells. Molecular docking suggested that NSE can bind to the active centers of both NS3 serine protease and HCV NS5B-polymerase and has an inhibitory effect on their activity. Conclusions. The obtained data confirm that using NSE is promising for the development of antiviral drug to suppress the HCV activity.

GLUCOSE-SENSITIVE PEPTIDE HORMONES

The present invention relates to a conjugate of the formula P-L-I, wherein P is a peptide hormone effecting the metabolism of carbohydrates in vivo, L is a hydrolysable linker molecule consisting of Lp and Lj, and I is a molecule capable of inhibiting the effect of the peptide hormone P on the metabolism of carbohydrates in vivo. Under in vivo conditions, the conjugate is the major compound. When the concentration of glucose increases in v/vo,the concentration of the peptide hormone effecting the metabolism of carbohydrates in vivo also increases.

A Convenient Protocol for the Synthesis of Fatty Acid Amides

Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.

Improved fatty acid monoethanolamide synthesis method

The invention relates to an improved fatty acid monoethanolamide synthesis method, which comprises: 1) preparing a polystyrene resin containing a carboxyl activating agent; 2) carrying out a condensation reaction on the polystyrene resin obtained in the step (1) and fatty acid in the presence of a catalyst to obtain an immobilized active ester; and (3) in the presence of a solvent, carrying out a reaction on the immobilized active ester obtained in the step 2) and ethanolamine, carrying out simple filtration or centrifugation to remove the resin after completing the reaction, carrying out pressure reducing concentration on the obtained liquid phase, and carrying out vacuum drying to obtain the high-quality fatty acid monoethanolamide product. According to the present invention, the condensation reaction is performed under the normal temperature condition, the generation of the by-product is substantially reduced through the selection of the catalyst and the reaction parameters, and the yield of the reaction and the purity of the product are maximized; and with the synthesis method, the defects of more by-products, difficult purification and the like caused by unstable raw material, poor selectivity to ethanolamine and alkali high temperature condition in the prior art are overcome.

Solvent-free “green” amidation of stearic acid for synthesis of biologically active alkylamides over iron supported heterogeneous catalysts

Stearoyl ethanolamine was synthesized by amidation of stearic acid with ethanolamine in solventless conditions. Iron containing heterogeneous catalysts supported on SiO2, Al2O3, Beta (BEA), ZSM-12 (MTW) and Ferrierite (FER) were used in this work. Sn-modified Ferrierite and H-Ferrierite were also studied for comparison. Fe-modified catalysts synthesized using solid state ion-exchange and evaporation impregnation methods, were thoroughly characterized with X-ray powder diffraction, scanning electron microscope, FTIR with pyridine, nitrogen adsorption, energy dispersive X-ray microanalysis and M?ssbauer spectroscopy. The highest conversion was obtained with Fe-H-FER-20 at 140?°C in 1?h giving 61% conversion and 98% selectivity towards the desired amide. The catalytic performance in terms of turnover frequency per mole of iron was achieved with the catalyst exhibiting the largest amount of Fe3+ species, optimum acidity and a relatively low Br?nsted to Lewis acid site ratio.

Fatty acid monoethanol amide succinate sulfonate and its preparation method and application

The invention provides a preparation method for fatty acid monoethanolamide succinate sulfonate. The preparation method is characterized by comprising the steps of generating amidation reaction by fatty acid and monoethanolamide to generate fatty acid monoethanolamide which is reacted with butenedioic acid or maleic anhydride to generate fatty acid monoethanolamide butenedioic acid ester, and generating salt formation reaction of the fatty acid monoethanolamide butenedioic acid ester and hydrosulphite to generate the fatty acid monoethanolamide succinate sulfonate. Compared with the prior art, trace cutting liquid prepared from the fatty acid monoethanolamide succinate sulfonate provided by the invention has high lubricating property, extreme pressure antiwear property and biological degradability; a high-end requirement on metal processing can be met only by using an extremely small amount of the trace cutting liquid; therefore, harm to the environment and workers is alleviated, and the pollution to the environment is reduced to the maximum extent.

A fatty acid monoethanol amide preparation method (by machine translation)

The invention discloses a fatty acid monoethanol amide preparation method, a fatty acid or a derivative thereof and a monoethanolamine according to a certain proportion, in the absence of solvent or mixed solvent system under full, add a certain amount of alkaline catalyst, under a certain temperature and stirring the reaction for a period of time, preparation of fatty acid monoethanolamine, this invention adopts the fatty acid or a derivative thereof as the amidation reaction preparation of fatty acid monoethanol amide of the acyl donor, has simple technological process, reaction efficiency. (by machine translation)

Pharmaceuticals and Surfactants from Alga-Derived Feedstock: Amidation of Fatty Acids and Their Derivatives with Amino Alcohols

Amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, was demonstrated with zeolites and mesoporous materials as catalysts and ethanolamine, alaninol, and leucinol. The last two can be derived from amino acids present in alga. The main products were fatty alkanol amides and the corresponding ester amines, as confirmed by NMR and IR spectroscopy. Thermal amidation of technical-grade oleic acid and stearic acid at 180°C with ethanolamine were non-negligible; both gave 61% conversion. In the amidation of stearic acid with ethanolamine, the conversion over H-Beta-150 was 80% after 3 h, whereas only 63% conversion was achieved for oleic acid; this shows that a microporous catalyst is not suitable for this acid and exhibits a wrinkled conformation. The highest selectivity to stearoyl ethanolamide of 92% was achieved with mildly acidic H-MCM-41 at 70% conversion in 3 h at 180°C. Highly acidic catalysts favored the formation of the ester amine, whereas the amide was obtained with a catalyst that exhibited an optimum acidity. The conversion levels achieved with different fatty acids in the range C12-C18 were similar; this shows that the fatty acid length does not affect the amidation rate. The amidation of methyl palmitate and biodiesel gave low conversions over an acidic catalyst, which suggested that the reaction mechanism in the amidation of esters was different. Pores versus acidity: The structures and properties of zeolites and mesoporous materials are investigated as catalysts for the amidation of renewable feedstocks, such as fatty acids, esters, and Chlorella alga based biodiesel, with ethanolamine, alaninol, and leucinol as nitrogen sources.