What Is 11(Z),14(Z)-Eicosadienoic Acid Ethanolamide?

11(Z),14(Z)-Eicosadienoic acid ethanolamide is a member of the N-acylethanolamine (NAE) family of bioactive lipids. It is formed by the conjugation of 11(Z),14(Z)-eicosadienoic acid — a 20-carbon polyunsaturated fatty acid with two cis double bonds at positions 11 and 14 — with ethanolamine via an amide bond.

N-acylethanolamines are endogenous lipid mediators found in animal tissues and are structurally related to the endocannabinoid anandamide (arachidonoyl ethanolamide). This compound serves as a useful biochemical reference standard and research tool for studying fatty acid ethanolamide metabolism, receptor pharmacology, and lipid signaling networks.

Chemical Properties and Structure

The compound features a 20-carbon acyl chain with two methylene-interrupted cis double bonds at the 11 and 14 positions, classifying it as an n-6 series fatty acid ethanolamide. The ethanolamine head group confers amphiphilic character, influencing membrane interactions and solubility.

Key physicochemical considerations include:

• Acyl chain length: C20
• Degree of unsaturation: 2 (diene)
• Double bond positions and geometry: 11Z, 14Z (both cis)
• Functional groups: Amide bond, primary hydroxyl (ethanolamine)
• Solubility: Typically soluble in organic solvents such as ethanol, DMSO, and chloroform; limited aqueous solubility

Due to the presence of cis double bonds, the compound is susceptible to oxidative degradation. Researchers should handle it under inert atmosphere conditions where possible and store it appropriately to preserve integrity.

Storage, Handling, and Stability

Proper storage and handling are critical to maintaining the chemical integrity of 11(Z),14(Z)-Eicosadienoic acid ethanolamide. The following best practices are recommended:

• Storage temperature: Store at -20°C or below, protected from light and moisture.
• Atmosphere: Minimize exposure to oxygen; consider storage under argon or nitrogen.
• Solvent preparation: Prepare stock solutions in dry, degassed organic solvents (e.g., ethanol or DMSO). Aliquot to avoid repeated freeze-thaw cycles.
• Reconstitution: Allow vials to equilibrate to room temperature before opening to prevent condensation.
• Stability: Unsaturated fatty acid ethanolamides are generally susceptible to oxidation and hydrolysis; use freshly prepared solutions for sensitive assays.

Always consult the product's Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for compound-specific guidance.

Research Applications

11(Z),14(Z)-Eicosadienoic acid ethanolamide is primarily used as a research tool in the following areas:

• Endocannabinoid system research: As a structural analog of anandamide, it can be used to probe cannabinoid receptor selectivity and compare the pharmacological profiles of different N-acylethanolamines.
• Lipid metabolism studies: Used as a substrate or reference compound to investigate enzymes involved in NAE biosynthesis and degradation, such as N-acylphosphatidylethanolamine-hydrolyzing phospholipase D (NAPE-PLD) and fatty acid amide hydrolase (FAAH).
• Lipidomics: Serves as an analytical reference standard for mass spectrometry-based identification and quantification of N-acylethanolamines in biological matrices.
• Cell signaling studies: Investigates the role of less-characterized NAE species in cellular processes including inflammation, apoptosis, and energy metabolism.

Researchers are encouraged to validate experimental conditions with appropriate controls when using this compound in novel assay systems.

Ordering and Availability

11(Z),14(Z)-Eicosadienoic acid ethanolamide is available from Aladdin Scientific under SKU N929218. To place an order or request a quotation, please contact your local Aladdin Scientific representative or visit the product page on the Aladdin Scientific website.

For bulk quantities, custom packaging, or certificate of analysis requests, please reach out to the Aladdin Scientific customer service team. Ensure you reference the SKU number N929218 to expedite your inquiry.

All products are subject to Aladdin Scientific's standard terms and conditions regarding shipping, returns, and payment. Please review the current Safety Data Sheet (SDS) prior to use.