| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
|
||
| Other Sizes |
| Targets |
(all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester does not have a single defined molecular target like a drug; rather, as a polyunsaturated fatty acid (PUFA) ester, it interacts with multiple pathways involved in lipid metabolism and inflammation. Upon hydrolysis to the free fatty acid, it can activate peroxisome proliferator-activated receptors (PPARs), particularly PPAR-alpha, which regulates genes involved in fatty acid oxidation. It can also modulate the activity of transcription factors such as SREBP-1c, reducing hepatic lipogenesis. Additionally, it can be incorporated into cell membranes, affecting membrane fluidity and signaling. In the context of dyslipidemia, omega-3 PUFAs reduce triglyceride levels by inhibiting diacylglycerol acyltransferase (DGAT) and increasing beta-oxidation. They also have anti-inflammatory effects mediated in part through the reduction of NF-kappaB activation.
|
|---|---|
| ln Vitro |
In vitro, (all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester is typically hydrolyzed to the free acid by esterases, and the free fatty acid is the active species. In cell culture models (e.g., hepatocytes), the compound reduces triglyceride synthesis and secretion. It inhibits DGAT activity and increases mitochondrial and peroxisomal beta-oxidation of fatty acids, leading to reduced lipid accumulation. In macrophages, it has been shown to modulate inflammatory responses by reducing the production of pro-inflammatory cytokines (TNF-alpha, IL-6) and chemokines, likely via NF-kappaB pathway inhibition. It also influences the production of eicosanoids by competing with arachidonic acid for cyclooxygenase (COX) and lipoxygenase enzymes, shifting the profile toward less inflammatory mediators.
|
| ln Vivo |
In vivo activity of (all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester is consistent with the established effects of long-chain omega-3 fatty acids. In animal models of hyperlipidemia, oral administration reduces serum triglyceride and total cholesterol levels. In mice fed a high-fat diet, supplementation with this compound improves the lipid profile and reduces hepatic steatosis. In models of hypertension, it lowers blood pressure through its vasodilatory effects, mediated by improved endothelial function and increased nitric oxide (NO) bioavailability. It also exhibits anti-inflammatory and anti-thrombotic effects in vivo. Due to its 21-carbon chain and five double bonds, it may have distinct metabolic and biological properties compared to more common omega-3 fatty acids like EPA (20:5) and DHA (22:6).
|
| Enzyme Assay |
Standard protocols for assessing fatty acid uptake and metabolism in vitro using (all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester or its free acid form: (1) Culture hepatocytes (e.g., primary rat hepatocytes or HepG2 cells) in DMEM with 10% FBS. (2) Conjugate the fatty acid to fatty acid-free bovine serum albumin (BSA) at a 2:1 or 4:1 molar ratio to enhance solubility. (3) For fatty acid oxidation assays: incubate cells with [14C]-labeled fatty acid complexed to BSA for 2-4 hours. (4) Collect 14CO2 by trapping it in filter paper soaked with 2N NaOH. (5) Quantify radioactivity by scintillation counting. (6) For triglyceride synthesis: incubate cells with [3H]-glycerol or [14C]-acetate, extract lipids with chloroform:methanol (2:1), separate by TLC, and quantify incorporation into triglycerides. (7) For DGAT assay: prepare microsomes from liver or adipose tissue and measure the conversion of diacylglycerol and [14C]-acyl-CoA to [14C]-triacylglycerol.
|
| Cell Assay |
For studies on omega-3 fatty acid effects on lipoprotein metabolism: (1) Differentiate Caco-2 human intestinal epithelial cells on Transwell inserts to model intestinal absorption. (2) Incubate cells with the fatty acid ester or free acid in the apical compartment for 2-4 hours. (3) Collect basolateral medium and measure triglyceride-rich lipoproteins (chylomicrons). (4) For hepatocyte studies, treat HepG2 or primary hepatocytes with the compound (10-100 uM) for 24-48 hours. (5) Measure apolipoprotein B (apoB) secretion into the medium by ELISA. (6) Assess intracellular lipid accumulation by Oil Red O staining and triglyceride quantification. (7) For gene expression analysis, extract RNA, perform reverse transcription, and quantify expression of PPAR-alpha, CPT-1alpha, SREBP-1c, and FAS by qRT-PCR. (8) For protein analysis, prepare cell lysates and perform Western blotting for key enzymes involved in lipogenesis and beta-oxidation.
|
| Animal Protocol |
A standard in vivo protocol for evaluating the hypolipidemic and anti-inflammatory effects of (all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester in a rodent model: (1) Use male Sprague-Dawley rats (200-250 g) or C57BL/6 mice. (2) Induce hyperlipidemia by feeding a high-fat diet (HFD, 45% fat) for 4-6 weeks. (3) Administer the compound by oral gavage daily at doses of 50-200 mg/kg, formulated in corn oil or 0.5% carboxymethylcellulose (CMC) with 5% Tween 80. (4) Continue HFD feeding during treatment period (2-4 weeks). (5) Collect blood samples from the tail vein at baseline and at the end of the treatment period. (6) Measure serum triglycerides, total cholesterol, LDL-cholesterol, HDL-cholesterol, and glucose using enzymatic colorimetric kits. (7) At termination, euthanize animals, collect liver and epididymal white adipose tissue. (8) Extract lipids from liver tissue using chloroform:methanol and quantify triglyceride and cholesterol content. (9) Prepare liver homogenates for measurement of malondialdehyde (MDA) as an oxidative stress marker and glutathione (GSH) levels. (10) Perform H&E and Oil Red O staining on liver sections to assess steatosis.
|
| ADME/Pharmacokinetics |
Oral administration of (all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester results in hydrolysis to the free fatty acid by pancreatic and intestinal esterases prior to absorption. The free acid is absorbed in the small intestine, incorporated into chylomicrons, and transported via the lymphatic system to the systemic circulation. The pharmacokinetics follow a multi-compartmental model, with the free acid undergoing rapid distribution to tissues such as liver, adipose, and muscle. The elimination half-life in plasma is typically 2-5 hours in rodents. The compound is primarily metabolized by beta-oxidation in the mitochondria and peroxisomes, similar to other long-chain fatty acids. The ethyl ester formulation provides better oral bioavailability and stability compared to the free acid form, as it is less susceptible to oxidation. For storage, the compound should be kept at -20degC, sealed, and protected from light and moisture.
|
| Toxicity/Toxicokinetics |
(all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester is generally considered safe at the doses used in research. It is a dietary fatty acid found naturally in fish oils and other marine sources. No significant acute toxicity has been reported for this specific ethyl ester. Potential side effects associated with high-dose omega-3 PUFA intake may include gastrointestinal disturbances (nausea, diarrhea, fishy aftertaste), a prolonged bleeding time (due to anti-platelet effects), and a possible increase in LDL-cholesterol in some individuals. At very high doses, vitamin E stores may become depleted due to increased oxidative load. Pregnant and breastfeeding women: Generally considered safe at nutritional doses. The compound is not a drug and has not undergone formal toxicological evaluation by regulatory agencies. It is for research use only and not intended for human consumption as a therapeutic.
|
| Additional Infomation |
(all-Z)-6,9,12,15,18-Heneicosapentaenoic acid ethyl ester (CAS 131775-86-5) is a long-chain omega-3 polyunsaturated fatty acid ethyl ester with five double bonds. It is a fatty acid ester from marine oils and is used for the prophylaxis and treatment of hypertension, hypertriglyceridemia, and hypercholesterolemia. Its 21-carbon chain length (21:5) is relatively uncommon, with most research focused on the 20-carbon eicosapentaenoic acid (EPA, 20:5) and 22-carbon docosahexaenoic acid (DHA, 22:6). This compound may have distinct biological activities due to its unique carbon chain length and double bond positions. It is a pure, well-characterized compound for research into the comparative pharmacology of different omega-3 PUFAs. The compound is not an FDA-approved drug and has no clinical trial history. It is available as a research biochemical for lipid metabolism studies.
|
| Molecular Formula |
C23H36O2
|
|---|---|
| Molecular Weight |
344.53
|
| Exact Mass |
344.272
|
| CAS # |
131775-86-5
|
| PubChem CID |
12054554
|
| Appearance |
Typically exists as solids at room temperature
|
| LogP |
6.861
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
16
|
| Heavy Atom Count |
25
|
| Complexity |
439
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
CC/C=C\\C/C=C\\C/C=C\\C/C=C\\C/C=C\\CCCCC(=O)OCC
|
| InChi Key |
RKAKAVQIMCZXPE-AAQCHOMXSA-N
|
| InChi Code |
InChI=1S/C23H36O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23(24)25-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-22H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-
|
| Chemical Name |
ethyl (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoate
|
| Synonyms |
(All-Z)-6,9,12,15,18-heneicosadecapentaenoic acid ethyl ester
|
| 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) |
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
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 | 2.9025 mL | 14.5125 mL | 29.0250 mL | |
| 5 mM | 0.5805 mL | 2.9025 mL | 5.8050 mL | |
| 10 mM | 0.2903 mL | 1.4513 mL | 2.9025 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
