7545-20-2

Upstream product

• 112-80-1 cis-Octadecenoic acid 
• 141-43-5 ethanolamine 
• 1415264-52-6 O-oleoylethanolamide trifluoroacetate 
• 112-62-9 Methyl oleate 
• 60-33-3 linoleic acid 
• 112-77-6 (Z)-9-octadecenoyl chloride 

Downstream Products

• 6301-24-2 2-(8-heptadecenyl)-2-oxazoline 
• 2601-90-3 N-[(9Z)-1-oxo-9-octadecenyl]glycine 
• 183323-44-6 Phosphoric acid dibenzyl ester 2-((Z)-octadec-9-enoylamino)-ethyl ester 
• 24435-25-4 NAEPA 

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.

Chemical synthesizing method of N-oleoyl ethanolamine

The invention belongs to the technical field of N-oleoyl ethanolamine synthesizing and discloses a chemical synthesizing method of N-oleoyl ethanolamine. The chemical synthesizing method includes thesteps of S1, performing low-temperature stirring; S2, adding a mixed solution and N, N-dimethyl formamide; S3, adding triethylamine; S4, adding into amine mixed liquid, and stirring; S5, washing, extracting and performing vacuum concentration; S6, distilling to remove impurities; S7, silica gel column chromatography purification. The chemical synthesizing method has the advantages that the methodis simple, high in purification rate and applicable to large-batch factory production, and the synthesized pure N-oleoyl ethanolamine is free of impurities.

Involvement of reactive oxygen species in the oleoylethanolamide effects and its pyrazonilic analogue in melanoma cells

The search for more substances that effectively fight melanoma is extremely important, because of its aggressive nature. In this sense, the molecular hybridization is a promising strategy. The aim of this work is to evaluate whether the antiproliferative effect of the endocannabinoid oleoylethanolamide can be improved with the addition of a trifluoromethylated pyrazolinic nucleus on its structure in B16F10 cell line. The pyrazolinic analog was named oleoyl pyrazoline. We also compared the effects of oleoylethanolamide and that of the classic endocannabinoid anandamide (AEA). The cell viability was evaluated by MTT assay, the intracellular reactive oxygen species generation by fluorimetry, and apoptosis/necrosis by fluorescent microscopy. Also, α-tocopherol antioxidant was used to evaluate the involvement of reactive oxygen species in the cellular response. Although the effects of AEA occur in smaller concentrations, the results show that the effects of AEA and oleoylethanolamide were similar. The results showed a decrease in cell viability, induction of apoptosis and necrosis, and increased generation of reactive oxygen species by the oleoylethanolamide, while the oleoyl pyrazoline increased cell proliferation and decreased reactive oxygen species. Additionally, the effects of oleoylethanolamide in cell viability were decreased by inhibiting the generation of reactive oxygen species by α-tocopherol. Therefore, it is possible to suggest the involvement of reactive oxygen species in the effect of oleoylethanolamide in the B16F10 cells. Considering the great need to find substances that can fight melanoma and the lack of greater elucidation in the action mechanisms of cannabinoids and their analogs, this work provides important new information that could serve as reference to other studies.

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.

COMPOSITION FOR PROMOTING HAIR GROWTH OR PREVENTING HAIR LOSS

The present invention relates to a composition for promoting hair growth, preventing hair loss, or relieving inflammation, and more specifically, to a composition which has excellent stability to the skin, has no side effects, and exhibits excellent effects of hair growth promotion and hair loss prevention by promoting hair growth and delaying hair loss. The composition according to the present invention contains a material belonging to a ceramidase inhibitor, glycol, C1-C5 lower alcohol, and water, and thus the composition is safe, has no side effects, can be continuously used for a long period of time, has an excellent effect of hair growth promotion or hair loss prevention by significantly promoting hair growth, and exhibits an inflammation relieving effect as well as a hair growth promoting effect, additionally.

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.

Scalable synthesis of oleoyl ethanolamide by chemical amidation in a mixed solvent

Oleoyl ethanolamide is a lipid mediator that exhibits biological activity in animal and cell models. In this study, an effective process is described to synthesize oleoyl ethanolamide by chemical amidation with native oil used as an acyl donor in the presence of sodium methoxide. Reaction conditions were optimized. When the amidation reaction was conducted in a mixed solvent, by reacting 2 mmol high oleic sunflower oil and 20 mmol ethanolamine in the presence of 1.5 % sodium methoxide with agitation, >90 % fatty acid ethanolamide was formed after 3 h of reaction time. The fatty acid ethanolamide product was purified by a two-step crystallization process to prepare oleoyl ethanolamide. Highly pure oleoyl ethanolamide was obtained in a 70.3 % molar yield. The novelty of the work is the use of native oil as acyl donor and the mixed solvent used as the reaction media. The use of native oil avoids the formation of ion pairs with ethanolamine that can occur in other synthesis routes.

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)

Synthesis and evaluation of fatty acid amides on the N-oleoylethanolamide-like activation of peroxisome proliferator activated receptor α

A series of fatty acid amides were synthesized and their peroxisome proliferator-activated receptor α (PPAR-α) agonistic activities were evaluated in a normal rat liver cell line, clone 9. The mRNAs of the PPAR-α downstream genes, carnitine-palmitoyltransferase-1 and mitochondrial 3-hydroxy-3-methylglutaryl-CoA synthase, were determined by real-time reverse transcription-polymerase chain reaction (RT-PCR) as PPAR-α agonistic activities. We prepared nine oleic acid amides. Their PPAR-α agonistic activities were, in decreasing order, N-oleoylhistamine (OLHA), N-oleoylglycine, Oleamide, N-oleoyltyramine, N-oleoylsertonin, and Olvanil. The highest activity was found with OLHA. We prepared and evaluated nine N-acylhistamines (N-acyl-HAs). Of these, OLHA, C16:0-HA, and C18:1Δ9-trans-HA showed similar activity. Activity due to the different chain length of the saturated fatty acid peaked at C16:0-HA. The PPAR-α antagonist, GW6471, inhibited the induction of the PPAR-α downstream genes by OLHA and N-oleoylethanolamide (OEA). These data suggest that N-acyl-HAs could be considered new PPAR-α agonists.

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.