Synthesis of oleoylethanolamide using lipase
Xiaosan Wang1, Xingguo Wang, Tong Wang
1State Key Laboratory of Food Science and Technology, School of Food Science and Technology, Jiangnan University, No 1800 Lihu Road, Wuxi, Jiangsu 214122, People's Republic of China.
Journal of Agricultural and Food Chemistry
|November 30, 2011
Summary
This study details an effective enzymatic synthesis for high-purity oleoylethanolamide (OEA). The optimized process is scalable and cost-effective, enabling further research into OEA
Area of Science:
- Biocatalysis and Enzymatic Synthesis
- Lipid Chemistry and Metabolism
Background:
- Oleoylethanolamide (OEA) is a fatty acid amide with significant biological roles.
- Previous synthesis methods for OEA often lack efficiency and economic viability.
- High-purity OEA is crucial for accurate biological and nutritional studies.
Purpose of the Study:
- To develop an effective and economically feasible enzymatic process for synthesizing high-purity oleoylethanolamide.
- To optimize reaction conditions for the amidation of oleic acid and ethanolamine.
- To assess the scalability of the optimized synthesis process.
Main Methods:
- Purification of commercial oleic acid.
- Optimization of enzymatic amidation using lipase in hexane.
- Scale-up of the synthesis reaction (50 mmol scale).
- Purification of synthesized oleoylethanolamide via crystallization.
Main Results:
- Optimized reaction conditions yielded oleoylethanolamide with 96.6% purity.
- Large-scale synthesis achieved 96.1% purity and 73.5% yield after crystallization.
- The developed method is more effective and economically feasible than previous approaches.
Conclusions:
- An efficient, scalable, and cost-effective enzymatic synthesis for high-purity oleoylethanolamide has been established.
- The process facilitates further investigation into the biological and nutritional functions of OEA.
- This method supports the study of OEA in animal and human subjects.
Related Concept Videos
01:14Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
01:07Alkylation of β-Ketoester Enolates: Acetoacetic Ester Synthesis
Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an alkylated β-keto acid.
01:27Synthesis of Phosphatidylcholine in the ER Membrane
The ER synthesizes lipids for building cell membranes and performing cellular functions such as energy storage and signaling. The lipid synthesis machinery embedded in the ER membrane primarily collects all reactants from the cytosol. Following synthesis, the secretory pathway and the ER contact sites distribute these lipids to other cellular organelles. Additionally, the energy-rich triacylglycerides are transported from the ER via lipid droplets.
The major components of all eukaryotic cell...
The major components of all eukaryotic cell...
01:29Biosynthesis of Lipids
Microbial membranes exhibit remarkable diversity in lipid composition, reflecting evolutionary adaptations to various environmental conditions. The three domains of life—Bacteria, Archaea, and Eukarya—synthesize membrane lipids through distinct biosynthetic pathways, leading to fundamental structural differences that impact membrane stability, function, and adaptability.Fatty Acid-Based Lipids in Bacteria and EukaryaBacteria and eukaryotes share a common fatty acid biosynthesis pathway, which...
01:25Esters to Carboxylic Acids: Saponification
Esters can be hydrolyzed to carboxylic acids under acidic or basic conditions. Base-promoted hydrolysis of esters is a nucleophilic acyl substitution reaction in which esters react with an aqueous base, followed by an acid to give carboxylic acids. This reaction is also known as saponification because it forms the basis for making soaps from fats.
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
The reaction requires a base in stoichiometric amounts, which participates in the reaction and is not regenerated later. So, the base acts as a...
02:44Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.