11(Z),14(Z)-Eicosadienoic Acid Ethanolamide: Research Guide

11(Z),14(Z)-Eicosadienoic acid ethanolamide is a synthetic fatty acid ethanolamide featuring a 20-carbon backbone with two cis double bonds at positions 11 and 14, structurally related to endogenous lipid mediators studied in the context of endocannabinoid signaling and lipid biochemistry research.

Product Name

11(Z),14(Z)-Eicosadienoic acid ethanolamide

SKU

N929218

Compound Class

Fatty acid ethanolamide (FAE)

Carbon Chain Length

20 carbons (eicosanoyl backbone)

Double Bond Configuration

Two cis (Z) double bonds at C11 and C14

Functional Group

Ethanolamide (amide-linked ethanolamine)

Recommended Storage

-20°C, protected from light and moisture (review flag: confirm with CoA)

Chemical Identity and Structure

11(Z),14(Z)-Eicosadienoic acid ethanolamide is a member of the fatty acid ethanolamide (FAE) family. Its backbone consists of a 20-carbon (eicosanoyl) acyl chain bearing two methylene-interrupted cis (Z) double bonds at the 11 and 14 positions, amide-linked to ethanolamine. This structural motif places it within the broader class of N-acylethanolamines (NAEs), which includes well-characterized bioactive lipids such as anandamide (arachidonoyl ethanolamide, AEA) and palmitoylethanolamide (PEA).

The two (Z)-configured double bonds confer conformational flexibility and influence the molecule's interaction with lipid-binding proteins and membrane environments. The ethanolamine head group provides a polar terminus capable of hydrogen bonding, while the polyunsaturated acyl chain contributes hydrophobicity. Together, these features are relevant to studies probing structure–activity relationships within the FAE class.

Physicochemical Properties and Formulation

As a long-chain unsaturated fatty acid ethanolamide, 11(Z),14(Z)-Eicosadienoic acid ethanolamide is expected to be a waxy solid or viscous oil at room temperature, with limited aqueous solubility due to its hydrophobic acyl chain. Researchers typically dissolve FAEs in organic solvents such as ethanol, DMSO, or dimethylformamide (DMF) to prepare stock solutions.

For cell-based or biochemical assays, stock solutions should be further diluted into aqueous buffers or culture media immediately before use, keeping the final organic solvent concentration below cytotoxic thresholds (commonly ≤0.1% v/v for DMSO or ethanol). Vehicle controls at matched solvent concentrations are strongly recommended in all biological experiments.

Due to the presence of bis-allylic methylene groups flanking the Z,Z-diene system, the compound may be susceptible to oxidative degradation. Working under inert atmosphere (argon or nitrogen) when handling concentrated stocks and storing aliquots under argon at −20 °C can help preserve integrity. Verification of compound purity by HPLC or NMR prior to biological testing is advised.

Research Applications

11(Z),14(Z)-Eicosadienoic acid ethanolamide serves as a research tool in the study of the endocannabinoid system and fatty acid ethanolamide biology. Its structural similarity to anandamide and other NAEs makes it a candidate probe for investigating substrate specificity of FAE-metabolizing enzymes, including fatty acid amide hydrolase (FAAH) and N-acylphosphatidylethanolamine-hydrolyzing phospholipase D (NAPE-PLD).

The compound may be used in competitive binding or displacement assays to characterize cannabinoid receptor pharmacology, as well as in mass spectrometry-based lipidomics workflows as a reference standard or internal standard candidate for related eicosadienoyl species. Researchers studying dietary fatty acid metabolism, lipid signaling, or neuromodulation may also employ this compound to examine how chain length and degree of unsaturation influence FAE bioactivity.

Due to limited published data specific to this compound, experimental observations should be interpreted with appropriate controls, and researchers are encouraged to contribute findings to the primary literature to expand the understanding of this FAE species.

Handling, Safety, and Storage Guidelines

Handle 11(Z),14(Z)-Eicosadienoic acid ethanolamide using standard laboratory safety precautions appropriate for fine research chemicals. Wear appropriate personal protective equipment (PPE), including nitrile gloves, laboratory coat, and safety glasses. Avoid inhalation of dusts or aerosols and contact with skin and eyes.

Store the compound at −20 °C in a tightly sealed vial, protected from light, heat, and moisture. Repeated freeze–thaw cycles should be minimized by preparing single-use aliquots. Consult the product's Safety Data Sheet (SDS) and Certificate of Analysis (CoA) for lot-specific purity data, exact storage conditions, and any compound-specific hazard classifications before use.

Dispose of waste containing this compound in accordance with applicable local, national, and institutional regulations governing chemical waste disposal.

Quality, Purity, and Verification

Aladdin Scientific supplies 11(Z),14(Z)-Eicosadienoic acid ethanolamide (SKU N929218) as a research-grade reagent. Researchers should consult the Certificate of Analysis (CoA) provided with each lot for purity specification, analytical data, and recommended handling conditions specific to that batch.

For applications requiring high quantitative accuracy—such as mass spectrometry calibration, enzyme kinetics, or receptor pharmacology studies—independent verification of compound identity and purity is recommended. Suitable analytical techniques include reversed-phase HPLC with UV or evaporative light-scattering detection, high-resolution mass spectrometry (HRMS), and proton NMR spectroscopy. Verification of double-bond geometry (Z/E) may be achieved by comparison of NMR chemical shifts and coupling constants with literature values for structurally related FAEs.

If degradation is suspected (e.g., color change, precipitation, or anomalous bioassay results), re-analysis of the stock solution is advised before drawing experimental conclusions.

Frequently asked questions

What solvents are recommended for dissolving 11(Z),14(Z)-Eicosadienoic acid ethanolamide?

Ethanol, DMSO, or DMF are commonly used to prepare stock solutions of fatty acid ethanolamides. For biological assays, dilute the stock into aqueous buffer or culture medium immediately before use and keep the final organic solvent concentration below 0.1% v/v to avoid cytotoxicity. Always include matched vehicle controls.

How should N929218 be stored to maintain compound stability?

Store at −20 °C in a tightly sealed vial, protected from light and moisture. Prepare single-use aliquots to avoid repeated freeze–thaw cycles, and consider storing under an inert gas (argon or nitrogen) to minimize oxidative degradation of the bis-allylic positions in the diene system. Confirm exact storage conditions with the lot-specific CoA.

Is 11(Z),14(Z)-Eicosadienoic acid ethanolamide a cannabinoid receptor ligand?

Its structural similarity to anandamide suggests potential interaction with cannabinoid receptors (CB1/CB2), but specific binding affinity data for this compound are not well established in the published literature. It is best used as a structural analog probe for comparative studies. Researchers should perform direct receptor binding assays to characterize its pharmacological profile.

Can this compound be used as an internal standard in lipidomics experiments?

11(Z),14(Z)-Eicosadienoic acid ethanolamide may serve as a reference or surrogate standard for related eicosadienoyl ethanolamide species in mass spectrometry-based lipidomics, provided its purity and identity are independently verified. For quantitative lipidomics, isotopically labeled internal standards are generally preferred when available.

Where can I find the Certificate of Analysis and Safety Data Sheet for N929218?

The Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for N929218 are available through the Aladdin Scientific website product page or by contacting Aladdin Scientific customer support directly. Always consult the lot-specific CoA for purity and storage data relevant to your batch.

References

1. Devane WA, et al. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 1992;258(5090):1946–1949. doi:10.1126/science.1470919
2. Ueda N, Tsuboi K, Uyama T. N-acylethanolamine metabolism with special reference to N-acylethanolamine-hydrolyzing acid amidase. Prog Lipid Res. 2010;49(4):299–315. doi:10.1016/j.plipres.2010.01.001
3. Cravatt BF, et al. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 1996;384(6604):83–87. doi:10.1038/384083a0
4. PubChem Compound Summary for 11(Z),14(Z)-Eicosadienoic acid ethanolamide. National Library of Medicine. https://pubchem.ncbi.nlm.nih.gov/

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.