| Size | Price | Stock | Qty |
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| 1mg |
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| 100mg | |||
| Other Sizes |
| Targets |
Eicosatetraynoic acid targets cyclooxygenase (COX) and lipoxygenase (LOX) enzymes, which are key enzymes in the arachidonic acid cascade that produce prostaglandins, thromboxanes, and leukotrienes. COX and LOX are involved in inflammation, pain, and platelet aggregation. By inhibiting both COX and LOX, ETYA blocks the production of pro-inflammatory eicosanoids. The compound also activates PPARalpha and PPARgamma chimeras at 10 microM, indicating activity at nuclear receptors involved in lipid metabolism and inflammation. ETYA specifically interferes with the replication of cowpox virus both in vivo and in vitro.
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| ln Vitro |
In vitro, Eicosatetraynoic acid inhibits cyclooxygenase and lipoxygenase with IC₅0 values of 8 microM and 4 microM, respectively. The compound is a nonspecific inhibitor of arachidonic acid metabolism. At 10 microM, ETYA activates PPARalpha and PPARgamma chimeras. The compound contains an alkyne group, enabling click chemistry applications for labeling and detection. ETYA also specifically interferes with the replication of cowpox virus both in vivo and in vitro, suggesting antiviral activity. The compound is used in research to study lipid signaling, inflammation, and viral infection.
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| ln Vivo |
In vivo, Eicosatetraynoic acid has been shown to interfere with the replication of cowpox virus. The compound's inhibition of arachidonic acid metabolism supports studies of lipid signaling during viral infection and host-virus interactions. ETYA enables exploration of prostaglandin-mediated modulation of immune responses. However, specific in vivo efficacy data, pharmacokinetic profiles, and dosing regimens are limited in publicly available sources. The compound is sensitive to air and light and should be handled accordingly. It is intended for research use only.
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| Enzyme Assay |
In vitro enzyme assays for Eicosatetraynoic acid involve measuring COX and LOX enzyme activities. For COX assays, the enzyme (COX-1 or COX-2) is incubated with arachidonic acid substrate and varying concentrations of ETYA (0.1-100 microM) in assay buffer at 37degC for 5-10 minutes. The reaction is stopped, and prostaglandin products (PGE2, PGF2alpha, TXB2) are quantified by ELISA or LC-MS/MS. IC₅0 values for COX inhibition are determined from dose-response curves. For LOX assays, lipoxygenase is incubated with arachidonic acid and ETYA, and products (5-HETE, 12-HETE, 15-HETE) are quantified by HPLC or LC-MS/MS. IC₅0 values for LOX inhibition are calculated.
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| Cell Assay |
Cellular assays for Eicosatetraynoic acid are performed using immune cells such as macrophages (RAW 264.7) or platelets. Cells are cultured in appropriate medium and seeded in 6- or 96-well plates. Cells are treated with serial dilutions of ETYA (0.1-100 microM) for 1-2 hours prior to stimulation with LPS (macrophages) or arachidonic acid (platelets). Prostaglandin and leukotriene levels in culture supernatants are measured by ELISA or LC-MS/MS. Cell viability is assessed by MTT assay. PPAR activation is assessed using a luciferase reporter assay in cells transfected with PPAR response element (PPRE)-luciferase constructs.
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| Animal Protocol |
In vivo animal studies for Eicosatetraynoic acid are conducted in models of inflammation, pain, and viral infection. In typical protocols, mice or rats are administered ETYA intraperitoneally or orally at doses of 10-100 mg/kg. In inflammatory models (e.g., carrageenan-induced paw edema), paw swelling is measured. In pain models, pain behaviors are assessed. In viral infection models (e.g., cowpox virus), viral titers and survival are monitored. Arachidonic acid metabolites in plasma and tissues are measured by LC-MS/MS. Pharmacokinetic parameters are determined from plasma samples. Efficacy is compared to vehicle control and standard anti-inflammatory agents.
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| ADME/Pharmacokinetics |
Eicosatetraynoic acid (CAS#: 1191-85-1) has molecular formula C20H24O2 and molecular weight 296.40. The compound is also known as ETYA, 5,8,11,14-eicosatetraynoic acid, and octadehydroarachidonic acid. It is a potent inhibitor of cyclooxygenase (IC₅0 = 8 microM) and lipoxygenase (IC₅0 = 4 microM). The compound activates PPARalpha and PPARgamma chimeras at 10 microM. It contains an alkyne group and can be used as a click chemistry reagent. Purity is typically ≥98%. The compound is air and light sensitive. Storage should be at -20degC, protected from light. For research use only.
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| References |
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| Additional Infomation |
Eicosapentaenoic acid (ECA) is a long-chain fatty acid. It is a 20-carbon unsaturated fatty acid containing four alkyne bonds. It can inhibit the enzymatic conversion of arachidonic acid into prostaglandins E(2) and F(2a).
Eicosatetraynoic acid (CAS#: 1191-85-1), also known as ETYA (5,8,11,14-eicosatetraynoic acid), is a potent inhibitor of cyclooxygenase (COX) and lipoxygenase (LOX), with IC₅0 values of 8 microM and 4 microM, respectively. By inhibiting both COX and LOX, ETYA blocks the production of pro-inflammatory eicosanoids including prostaglandins, thromboxanes, and leukotrienes. The compound also activates PPARalpha and PPARgamma chimeras at 10 microM and interferes with cowpox virus replication. ETYA contains an alkyne group, making it a click chemistry reagent. The compound is used in research to study lipid signaling, inflammation, and viral infection. As of the current date, Eicosatetraynoic acid is not approved for clinical use. |
| Molecular Formula |
C20H24O2
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|---|---|
| Molecular Weight |
296.40336
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| Exact Mass |
296.177
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| CAS # |
1191-85-1
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| PubChem CID |
1780
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| Appearance |
Light yellow to brown solid powder
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
490.3±45.0 °C at 760 mmHg
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| Melting Point |
79-81ºC
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| Flash Point |
226.6±23.4 °C
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| Vapour Pressure |
0.0±2.7 mmHg at 25°C
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| Index of Refraction |
1.528
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| LogP |
5.19
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
6
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| Heavy Atom Count |
22
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| Complexity |
586
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| Defined Atom Stereocenter Count |
0
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| InChi Key |
MGLDCXPLYOWQRP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C20H24O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h2-5,8,11,14,17-19H2,1H3,(H,21,22)
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| Chemical Name |
icosa-5,8,11,14-tetraynoic acid
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~2 mg/mL (~6.75 mM)
Ethanol : ~1 mg/mL (~3.37 mM) |
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| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3738 mL | 16.8691 mL | 33.7382 mL | |
| 5 mM | 0.6748 mL | 3.3738 mL | 6.7476 mL | |
| 10 mM | 0.3374 mL | 1.6869 mL | 3.3738 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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