| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Other Sizes |
| Targets |
The primary metabolic targets of cis-9,10-Epoxystearic acid are epoxide hydrolases (specifically microsomal and cytosolic epoxide hydrolase) which hydrate the epoxide ring to form the corresponding diol (threo-9,10-dihydroxystearic acid). It is also a substrate for phospholipase A2 (PLA2) when incorporated into phospholipids. As an oxidized lipid, it can modulate inflammatory signaling pathways and membrane fluidity.
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|---|---|
| ln Vitro |
In vitro studies show that cis-9,10-Epoxystearic acid exhibits inhibitory effects on certain enzymes. For example, it can inhibit epoxide hydrolase activity at higher concentrations (substrate inhibition) or modify the activity of ion channels. When incorporated into lipid bilayers, it increases membrane permeability. It is also used to study the substrate specificity of various lipases. Compared to its monoenoic precursor (oleic acid), the epoxidized form is hydrolyzed by PLA2 at a 2-fold faster rate.
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| ln Vivo |
In vivo, cis-9,10-Epoxystearic acid is considered a bioactive lipid mediator. It is formed during oxidative stress and inflammation. Its activity is generally short-lived as it is rapidly metabolized by soluble epoxide hydrolase (sEH) to the less reactive diol. However, if epoxide hydrolase is inhibited, the epoxide can accumulate and potentially exert cytotoxic effects by covalently modifying proteins or disrupting membrane integrity. Animal studies often focus on its role in atherosclerosis.
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| Enzyme Assay |
A non-cellular assay utilizes purified enzymes. Porcine pancreatic phospholipase A2 (PLA2) is incubated with 1-palmitoyl-2-(cis-9,10-epoxystearoyl)-sn-glycero-3-phosphocholine (the phospholipid containing the epoxide) in Tris buffer (pH 8.0) containing CaCl2 at 40degC. The release of free cis-9,10-epoxystearic acid is monitored by GC-MS or by a pH-stat titrimetric method. Alternatively, the fatty acid epoxide is incubated with rat liver microsomes or purified epoxide hydrolase at 37degC; the diol product is extracted and quantified by HPLC.
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| Cell Assay |
Cell-based assays typically involve treating macrophages (e.g., RAW 264.7 cells) or endothelial cells with cis-9,10-Epoxystearic acid (1-50 uM) for 1-24 hours. Cells are then harvested, and lipids are extracted using the Bligh and Dyer method (chloroform:methanol). The lipid extract is analyzed by LC-MS/MS to identify the conversion of the epoxide to the diol. Alternatively, cells are pre-treated with epoxide hydrolase inhibitors (e.g., AUDA) before adding the epoxide to study the accumulation and biological effects of the epoxide itself.
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| Animal Protocol |
In animal experiments, cis-9,10-Epoxystearic acid is typically administered via intravenous or intraperitoneal injection in rodents (e.g., 1-10 mg/kg dissolved in ethanol/saline). Blood is collected at various time points, and tissues (liver, kidney, heart) are harvested after euthanasia. Lipids are extracted and analyzed by GC-MS or LC-MS/MS to quantify the epoxide/diol ratio. Alternatively, the compound is fed as part of a high-fat diet to study its effects on atherosclerosis in ApoE-/- mice.
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| ADME/Pharmacokinetics |
As an endogenous metabolite, the pharmacokinetics of cis-9,10-Epoxystearic acid involves rapid clearance. Its plasma half-life is typically very short (minutes) due to rapid hydration by soluble epoxide hydrolase (sEH) in the liver and kidney. It is transported in the blood bound to albumin. The primary route of elimination is as the dihydroxystearic acid metabolite in urine and feces. Because it is highly lipophilic, it partitions readily into cell membranes.
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| Toxicity/Toxicokinetics |
Toxicologically, cis-9,10-Epoxystearic acid is considered a cytotoxic lipid mediator when accumulated. High levels can cause mitochondrial dysfunction, endoplasmic reticulum stress, and cell death. It is more toxic than its corresponding diol. However, under normal physiological conditions, endogenous concentrations are tightly regulated by epoxide hydrolases. In standard laboratory handling, it is considered a non-hazardous chemical; however, prolonged exposure to air may cause oxidation.
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| References | |
| Additional Infomation |
9,10-Epoxyoctadecanoic acid is an epoxy fatty acid composed of octadecanoic acid (stearic acid) with an epoxy group attached between the 9 and 10 positions. It is a human metabolite and the conjugate acid of 9,10-epoxyoctadecanoic acid ester.
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| Molecular Formula |
C18H34O3
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|---|---|
| Molecular Weight |
298.46
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| Exact Mass |
298.251
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| CAS # |
24560-98-3
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| Related CAS # |
61792-39-0 (ammonium salt)
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| PubChem CID |
15868
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| Appearance |
White to off-white solid powder
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| Density |
0.956g/cm3
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| Boiling Point |
422.9ºC at 760mmHg
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| Flash Point |
141.1ºC
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| Vapour Pressure |
2.46E-08mmHg at 25°C
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| Index of Refraction |
1.467
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| LogP |
5.319
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
15
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| Heavy Atom Count |
21
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| Complexity |
265
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CCCCCCCC[C@H]1O[C@H]1CCCCCCCC(=O)O
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| InChi Key |
IMYZYCNQZDBZBQ-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C18H34O3/c1-2-3-4-5-7-10-13-16-17(21-16)14-11-8-6-9-12-15-18(19)20/h16-17H,2-15H2,1H3,(H,19,20)
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| Chemical Name |
8-(3-octyloxiran-2-yl)octanoic 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 |
| 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 :~100 mg/mL (~335.05 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.38 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.38 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.3505 mL | 16.7527 mL | 33.5053 mL | |
| 5 mM | 0.6701 mL | 3.3505 mL | 6.7011 mL | |
| 10 mM | 0.3351 mL | 1.6753 mL | 3.3505 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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