| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Ethyl linoleate targets multiple pathways and enzymes. It inhibits the Akt/GSK3β/β-catenin signaling pathway and blocks NF-κB activation. It induces heme oxygenase-1 (HO-1) and inhibits tyrosinase. These activities contribute to its anti-inflammatory, whitening, and anti-atherosclerotic effects. It also promotes compound absorption.
|
|---|---|
| ln Vitro |
In vitro, ethyl linoleate (400 µM; 48 h) significantly inhibits melanin content and intracellular tyrosinase activity in α-MSH-induced B16F10 cells. It (1-20 µM; 1-24 h) attenuates lipopolysaccharide-induced pro-inflammatory cytokine production by inducing HO-1 in RAW264.7 cells. It inhibits the development of atherosclerotic lesions and the expression of inflammatory mediators.
|
| ln Vivo |
In vivo, ethyl linoleate (10% added to a high-cholesterol diet; p.o.; 12 weeks) has a significant effect on atherosclerosis induced by a high-cholesterol diet in rabbits. It increased body weight, accelerated the increase of serum and liver cholesterol levels, caused fatty infiltration in the liver and spleen, but reduced atherosclerotic proliferation of the aorta and kidneys.
|
| Enzyme Assay |
In vitro assays for ethyl linoleate typically involve cell viability, melanin content, and tyrosinase activity assays. A standard protocol for melanogenesis inhibition involves culturing B16F10 melanoma cells and treating them with ethyl linoleate (typically 1-400 µM) for 48 hours. Melanin content is measured spectrophotometrically, and tyrosinase activity is assessed using L-DOPA as a substrate. For anti-inflammatory studies, RAW264.7 macrophages are treated with ethyl linoleate (1-20 µM) and stimulated with LPS, and cytokine production is measured by ELISA.
|
| Cell Assay |
In vitro cell culture experiments with ethyl linoleate typically involve B16F10 melanoma cells for melanogenesis studies or RAW264.7 macrophages for anti-inflammatory studies. Cells are cultured in appropriate media and treated with the compound at concentrations ranging from 1-400 µM for 24-48 hours. Cell viability is assessed using MTT assays. Melanin content, tyrosinase activity, and cytokine levels are measured.
|
| Animal Protocol |
In vivo animal studies with ethyl linoleate are conducted to study its effects on atherosclerosis. A typical protocol involves administering the compound orally to rabbits at a dose of 10% added to a high-cholesterol diet for 12 weeks. Serum and liver cholesterol levels, as well as atherosclerotic lesions in the aorta, are measured.
|
| ADME/Pharmacokinetics |
Ethyl linoleate is an orally active compound. Based on its physicochemical properties (molecular weight 308.50, soluble in DMSO at 100 mg/mL), it is expected to have good oral bioavailability. It is stored as a pure form at -20°C for up to 3 years.
|
| Toxicity/Toxicokinetics |
Ethyl linoleate is generally considered safe as a fatty acid ester. Standard laboratory safety precautions should be followed when handling this compound, including the use of gloves and safety glasses. It is not intended for drug, household, or other uses without further formulation and testing.
|
| References | |
| Additional Infomation |
Ethyl linoleate is a long-chain fatty acid ethyl ester formed by the condensation of the carboxyl group of linoleic acid and the hydroxyl group of ethanol. It is a plant metabolite and anti-inflammatory agent, functionally related to linoleic acid. Ethyl linoleate has been reported to exist in daphne, corn, and other organisms with relevant data.
Ethyl linoleate is an orally active unsaturated fatty acid with whitening, anti-inflammatory, and anti-atherosclerotic effects. It inhibits the Akt/GSK3β/β-catenin signaling pathway and NF-κB activation. It is used in research on inflammatory diseases and can be used in cosmetics. It has not undergone clinical trials and is not approved as a pharmaceutical. |
| Molecular Formula |
C20H36O2
|
|---|---|
| Molecular Weight |
308.50
|
| Exact Mass |
308.271
|
| CAS # |
544-35-4
|
| Related CAS # |
Ethyl linoleate-13C18; 202114-63-4; Ethyl linoleate-d2; 1404475-07-5
|
| PubChem CID |
5282184
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.9±0.1 g/cm3
|
| Boiling Point |
388.3±21.0 °C at 760 mmHg
|
| Flash Point |
96.3±20.4 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.465
|
| LogP |
8.17
|
| Hydrogen Bond Donor Count |
0
|
| 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\CCCCCCCC(=O)OCC
|
| InChi Key |
FMMOOAYVCKXGMF-MURFETPASA-N
|
| InChi Code |
InChI=1S/C20H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22-4-2/h8-9,11-12H,3-7,10,13-19H2,1-2H3/b9-8-,12-11-
|
| Chemical Name |
ethyl (9Z,12Z)-octadeca-9,12-dienoate
|
| Synonyms |
Ethyl linoleate
|
| 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)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (324.15 mM)
|
|---|---|
| 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 | 3.2415 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 |
*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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
