Synthesis Of Fatty Acid Amides Research Articles

Biocatalytic synthesis of lipophilic amides by the lipase of Candida antarctica type B

In this study, 37 fatty acid amides were obtained by CAL-B (Novozym 435) in 2 h, with yields up to 91%. The (S)-mandelic acid amides (3a-3l, 14–91%), salicylic acid amides (3m-3y, 57–90%), and 3-(4-hydroxyphenyl)propanoic acid amides (3z-3ak, 17–70%) were efficiently synthetized using different fatty acids in an esterification reaction catalyzed by CAL-B. An one-pot procedure was developed, and the fatty acid amide 3m was obtained in 63% after two-steps. The same procedure was applied using coconut oil, a product rich in triglycerides containing C12-C16 carbon chains, and the fatty acid amide 3al was obtained with 60% yield. These results represent an important contribution to the biocatalytic synthesis of fatty acid amides for possible cosmetic and pharmacological applications.

Single Cell Oil (SCO)-Based Bioactive Compounds: I-Enzymatic Synthesis of Fatty Acid Amides Using SCOs as Acyl Group Donors and Their Biological Activities.

Fatty acid amides (FAAs) are of great interest due to their broad industrial applications. They can be synthesized enzymatically with many advantages over chemical synthesis. In this study, the fatty acid moieties of lipids of Cunninghamella echinulata ATHUM 4411, Umbelopsis isabellina ATHUM 2935, Nannochloropsis gaditana CCAP 849/5, olive oil, and an eicosapentaenoic acid (EPA) concentrate were converted into their fatty acid methyl esters and used in the FAA (i.e., ethylene diamine amides) enzymatic synthesis, using lipases as biocatalysts. The FAA synthesis, monitored using in situ NMR, FT-IR, and thin-layer chromatography, was catalyzed efficiently by the immobilized Candida rugosa lipase. The synthesized FAAs exhibited a significant antimicrobial activity, especially those containing oleic acid in high proportions (i.e., derived from olive oil and U. isabellina oil), against several human pathogenic microorganisms, insecticidal activity against yellow fever mosquito, especially those of C. echinulata containing gamma-linolenic acid, and anticancer properties against SKOV-3 ovarian cancer cell line, especially those containing EPA in their structures (i.e., EPA concentrate and N. gaditana oil). We conclude that FAAs can be efficiently synthesized using microbial oils of different fatty acid composition and used in specific biological applications.

Chemoenzymatic Synthesis and Anti-Inflammatory Activity of Fatty Acid Amides Prepared from Bertholletia excelsa (Brazil Nut) Triglycerides

This study reports the synthesis of fatty acid amides (FAA), analogous to anandamide, prepared from Brazil nut oil (BNO), using Amano lipase from Pseudomonas fluorescens as a catalyst of direct aminolysis, with a good yield (95-68%). The anti-inflammatory effects of BNO and FAA were evaluated by the carrageenan-induced paw edema method. Analysis of the formation of edema showed that these FAA, at all dose used, significantly reduced the development of edema.

ChemInform Abstract: Nano Sulfated Titania as Solid Acid Catalyst in the Direct Synthesis of Fatty Acid Amides.

ChemInform Abstract: Nano Sulfated Titania as Solid Acid Catalyst in the Direct Synthesis of Fatty Acid Amides.

Nano Sulfated Titania as Solid Acid Catalyst in Direct Synthesis of Fatty Acid Amides

Nanosized sulfated titania was prepared by a sol-gel hydrothermal process. X-ray diffraction (XRD), transmission electron, and scanning electron micrographs (TEM and SEM), FT-IR specific surface area, and BET N(2) adsorption were employed to characterize the properties of the synthesized sulfated TiO(2). The results indicate that both anatase and rutile TiO(2) are obtainable. This prepared sulfated titania showed high catalytic activity in direct amidation of fatty acids as well as benzoic acids with various amines under solvent-free conditions.

Synthesis of Fatty Acid Amides of Catechol Metabolites that Exhibit Antiobesity Properties

A series of fatty acid amides of 3,4-methylenedioxymethamphetamine (MDMA) catechol metabolites were synthesized in order to evaluate their biological activities. Upon administration, all synthesized compounds resulted in negative modulation of food intake in rats. The most active compounds have affinity for the CB(1) receptor and/or PPAR-α; part of their biological activity may be caused by these double interactions.

Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

Recent biochemical and pharmacological studies have led to the characterization of different fatty acid amides as a new family of biologically active lipids. Here, we describe the synthesis of new amides from C16:0, 18:0, 18:1 and 18:1, OH fatty acids (FFA) families with cyclic and acyclic amines and demonstrate for the first time that these compounds produce citotoxic effects. Application of this method to the synthesis of fatty acid amides was performed using the esters aminolysis as a key step and various carboxylic amides were prepared in good yield from fatty acid methyl esters (FAMEs).

Lipase-catalysed ammoniolysis of lipids. A facile synthesis of fatty acid amides

Ammoniolysis of triglycerides to the corresponding fatty acid amides is efficiently catalysed by Candida antarctica lipase (Novozym 435). Thus, olive oil gave 90% of nearly pure oleamide after 72 h at 60°C. Jojoba wax was similarly converted into a mixture of cis-11-eicosenamide and erucamide together with cis-11-eicosenol and cis-l3-docosenol.