Synthesis of Oleoylethanolamide Using Lipase

Abstract

An effective process for the enzymatic synthesis of oleoylethanolamide is described in this study. The process included purification of a commercial oleic acid product and then optimization of the reaction between the purified oleic acid and ethanolamine in the presence of hexane and a lipase. Under the optimal amidation reaction conditions identified, oleoylethanolamide was obtained with 96.6% purity. The synthesis was also conducted on a large scale (50 mmol of each of the reactants), and oleoylethanolamide purity and yield after crystallization purification were 96.1 and 73.5%, respectively. Compared to the previous studies, the current method of preparing high-purity oleoylethanolamide is more effective and economically feasible. The scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like oleoylethanolamide in animal or human subjects. ABSTRACT: An effective process for the enzymatic synthesis of oleoylethanolamide is described in this study. The process included purification of a commercial oleic acid product and then optimization of the reaction between the purified oleic acid and ethanolamine in the presence of hexane and a lipase. Under the optimal amidation reaction conditions identified, oleoylethanolamide was obtained with 96.6% purity. The synthesis was also conducted on a large scale (50 mmol of each of the reactants), and oleoylethanolamide purity and yield after crystallization purification were 96.1 and 73.5%, respectively. Compared to the previous studies, the current method of preparing high-purity oleoylethanolamide is more effective and economically feasible. The scalability and ease for such synthesis make it possible to study the biological and nutritional functions of the cannabinoid-like oleoylethanolamide in animal or human subjects.

Catalytic amide formation from non-activated carboxylic acids and amines

“…The immobilized enzyme was also used by Wang et al for the amidation of oleic acid with ethanolamine on 55 a 50 mmol scale, yielding 74% of the amide after recrystallization. 41 The catalyst loading was 30% and the reactants were used in a 1:1 molar ratio.…”

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

“…Theo ther product was 2-stearamidoethyl stearate. The same columnwas also tested in our work;however,a ccording to our results, 2-stearamidoethyls tearate wasn ot eluted from the long capillaryc olumn, which could undermine the resultsr eportedb yW ang et al [26] Zeolite-catalyzed amidation of oleic acid was investigated by Musteata et al [23] and gave the fattya cid amide and amino ester as the main products, according to HPLC results without any further confirmation. [26] In their work, the only analytical methodu sed was GC with al ong capillary column.…”

“…The two main reactionp roducts eluted from as hort GC columna t1 4.6 and 22.3 min, respectively,w ith the corresponding selectivities of 85 and1 3%,r espectively.T he final product mixture after purification, according to the procedure reported by Fernandez-Perez and Otero, [25] contained 2-stearamidoethanol. [26] In their work, the only analytical methodu sed was GC with al ong capillary column. The current results are in agreement with the analogous products formed by lipase-catalyzed amidation of acids with ethanolamine, [25] for which the structures of the products were also confirmed by IR andN MR spectroscopy.O nthe other hand, lipase-catalyzed amidation of oleic acid with ethanolamine only resulted in the formation of amide, even if presence of aminoesterw as also speculated.…”

“…The aim is thus to decrease the E factor,w hich is defined as one kilogram of waste produced per kilogram of product. [23,24] Fatty acid amides can also be prepared in the presenceo fe nzymatic [25][26][27] or solid acid catalysts. To the best of our knowledge,t here are only af ew publications in the literature on catalytic amidation of fatty acids to give K-alkyl amides ( Figure 1).…”

Construction of a fractional condensation device and its application in the analysis of volatile compounds from tobacco

“…9 The simultaneous distillation and extraction can be coupled with GC/HPLC/GC-MS and widely applied to the analysis of meat, dairy products and beverages, condiments, grains, vegetables and essences. [10][11][12][13][14][15][16][17][18][19][20][21] For example, Montserrat Riu-Aumatell et al 22 analyzed more than 80 volatile compounds from white salsify by headspace-solid phase microextraction (HS-SPME) and SDE, leading to the identication of a majority of the sesquiterpenes, acids and esters with high molecular weight. Du Liping et al 23 compared the extraction performance of SPME and SDE in the determination of volatile compounds in pu-erh tea.…”