,14(Z)-Eicosadienoic acid Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C20H36O2 |
| Molecular Weight | 308.50 |
| Exact Mass | 308.271 |
| CAS # | 5598-38-9 |
| Related CAS # | 2091-39-6 |
| PubChem CID | 6439848 |
| Appearance | Colorless to light yellow liquid |
| Density | 0.9±0.1 g/cm3 |
| Boiling Point | 462.1±0.0 °C at 760 mmHg |
| Flash Point | 326.3±15.2 °C |
| Vapour Pressure | 0.0±2.4 mmHg at 25°C |
| Index of Refraction | 1.478 |
| LogP | 8.24 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 16 |
| Heavy Atom Count | 22 |
| Complexity | 292 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | CCCCC/C=C\C/C=C\CCCCCCCCCC(=O)O |
| InChi Key | XSXIVVZCUAHUJO-HZJYTTRNSA-N |
| InChi Code | InChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6-,10-9- |
| Chemical Name | (11Z,14Z)-icosa-11,14-dienoic acid |
| Synonyms | 5598-38-9; (11Z,14Z)-Icosa-11,14-dienoic acid; cis-11,14-Eicosadienoic acid; Eicosadienoic acid; HOMO-GAMMA-LINOLEICACID; Icosadienoic acid; 11,14-Icosadienoic acid; FA 20:2; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets |
Leukotriene B4 receptor (LTB4R)[2] 11(Z),14(Z)-Eicosadienoic acid acts as a competitive antagonist of the leukotriene B₄ (LTB₄) receptor with an IC₅₀ of 15 μM.[2] |
| ln Vitro |
11(Z),14(Z)-Eicosadienoic acid (10–100 μM) inhibits LTB₄-induced chemotaxis in human neutrophils by 60–85%, demonstrating functional blockade of LTB₄ receptor signaling.[2] It reduces LTB₄ binding to neutrophil membranes by 50% at 30 μM, confirming direct receptor antagonism.[2] |
| Enzyme Assay |
11(Z),14(Z)-Eicosadienoic acid (10–100 μM) inhibits LTB₄-induced chemotaxis in human neutrophils by 60–85%, demonstrating functional blockade of LTB₄ receptor signaling.[2] It reduces LTB₄ binding to neutrophil membranes by 50% at 30 μM, confirming direct receptor antagonism.[2] |
| Cell Assay | Neutrophil Chemotaxis: Human neutrophils were pre-treated with 11(Z),14(Z)-Eicosadienoic acid (10–100 μM) for 10 min, then placed in Boyden chambers. LTB₄ (10 nM)-directed migration was quantified after 45 min at 37°C.[2] |
| References |
[1]. Identification of naturally occurring trans, trans delta 5,9 fatty acids from the sponge Plakortis halichondroides. Lipids. 1990 Dec;25(12):835-40. [2]. Essential fatty acids are antagonists of the leukotriene B4 receptor. Prostaglandins Leukot Essent Fatty Acids. 1995 May;52(5):293-7. |
| Additional Infomation |
(11Z,14Z)-icosadienoic acid is an icosadienoic acid with double bonds at positions 11 and 14 (both Z). It has a role as a metabolite. It is a conjugate acid of an (11Z,14Z)-icosadienoate. It derives from a hydride of an icosanoic acid. Eicosadienoic acid has been reported in Salvia hispanica, Arbacia punctulata, and other organisms with data available. Eicosadienoic Acid is a polyunsaturated long-chain fatty acid with a 20-carbon backbone and exactly 2 double bonds. At least 5 different isomers can be called by this name. 11(Z),14(Z)-Eicosadienoic acid is a natural Δ5,9 fatty acid first isolated from the sponge Plakortis halichondroides, identified via GC-MS and NMR analysis of methyl esters.[1] As an essential fatty acid derivative, it competitively inhibits LTB₄ binding to its receptor on neutrophils, suggesting anti-inflammatory potential through disruption of neutrophil recruitment.[2] |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.2415 mL | 16.2075 mL | 32.4149 mL | |
| 5 mM | 0.6483 mL | 3.2415 mL | 6.4830 mL | |
| 10 mM | 0.3241 mL | 1.6207 mL | 3.2415 mL |