Synthesis of Linoleoyl Ethanolamide

Wang, Xiaosan; Chen, Yan; Jin, Qingzhe; Huang, Jianhua; Wang, Xingguo

doi:10.5650/jos.62.427

Cited by 19 publications

(13 citation statements)

References 24 publications

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“…The applied reaction conditions were adopted from Wang et al [29]. Briefly, ethanolamine (1.8 mmol) was mixed with the respective fatty acid methyl ester (0.06 mmol) in a 1.5-mL Eppendorf tube.…”

Section: Synthesis Of Faeasmentioning

confidence: 99%

“…As described by Wang et al [29], ethanolamine can be used both as solvent and reactant during reaction with methyl linoleate without further addition of other solvents. While this protocol worked well for cis6-, cis9-, and cis11-octadecanoic acid methyl esters, the synthesis of all transisomers varied greatly in terms of yield and purity.…”

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

“…Increasing ethanolamine to 30-fold instead of the original 10-fold excess resulted in a considerable improvement of all reactions but for the trans9-isomer. [29] to trans-fatty acids isomers. Thus, we were able to reliably synthesize a spectrum of cisand trans-octadecanoic ethanolamide isomers with quantitative conversion rates and excellent purity without complex purification steps.…”

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

“…In contrast to LC-ESI-MS/MS measurements, all compounds used during synthesis are reliably detected by GC-EI-MS with little variation of ionization efficiency between molecules, so that the purity of synthesis products can be examined with more detail and reliability. To increase the volatility of our standards, a silylation reaction adapted from Wang et al was performed [29]. Mass spectra resulting from electron ionization were highly similar between samples.…”

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

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Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

et al. 2016

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The endocannabinoid system is important in various physiological pathways, especially the regulation of food intake. It consists of endocannabinoids like 2-arachidonoyl-glycerol (2-AG) or the fatty acid ethanolamide archachidonoyl-ethanolamide (AEA) with binding affinity to cannabinoid receptors. Further, fatty acid ethanolamides (FAEAs) influence the endocannabinoid system without affecting cannabinoid receptors by using independent physiological pathways. Among FAEAs, oleic acid ethanolamide (OEA) gained importance because of its promising ability to reduce food intake. By ultrahigh-performance liquid chromatography-electrospray ionization-tandem mass spectrometry (UHPLC-ESI-MS/MS), we detected a chromatographically separated molecule in plasma samples from rats and humans with identical mass and fragmentation patterns as those of OEA. Via synthesis and extensive analysis of ethanolamides of different cis/trans- and position isomers of oleic acid (cis9-18:1), we could identify the unknown molecule as vaccenic acid (cis11-18:1) ethanolamide (VEA). In this study we identified VEA as the most abundant 18:1 FAEA in rat plasma and the second most abundant 18:1 FAEA in human plasma.

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Section: Synthesis Of Faeasmentioning

confidence: 99%

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

Section: Synthesis Of Oea and Oea-isomersmentioning

confidence: 99%

See 2 more Smart Citations

Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

et al. 2016

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“…Fatty acid ethanolamides are an important class of nonionic surfactants, which are widely used as lubricants, surfactants, detergents, and cosmetics [1][2][3]. Their physicochemical properties can differ depending on the length of the hydrocarbon chain.…”

Section: Introductionmentioning

confidence: 99%

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

Wang

Han

Chen

et al. 2015

J Americ Oil Chem Soc

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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.

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Kinetics in the thermal and catalytic amidation of C18 fatty acids with ethanolamine for the production of pharmaceuticals

Mäki‐Arvela

Kumar

Chapelliere

et al. 2016

Reac Kinet Mech Cat

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Synthesis of Linoleoyl Ethanolamide

Cited by 19 publications

References 24 publications

Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

Identification of the oleic acid ethanolamide (OEA) isomer cis-vaccenic acid ethanolamide (VEA) as a highly abundant 18:1 fatty acid ethanolamide in blood plasma from rats and humans

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

Kinetics in the thermal and catalytic amidation of C18 fatty acids with ethanolamine for the production of pharmaceuticals

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