| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg | |||
| Other Sizes |
| Targets |
Oleoyl coenzyme A lithium targets several proteins involved in metabolic and signaling pathways. It acts as a potent allosteric inhibitor of human 15-lipoxygenase-2 (h15-LOX-2) and also inhibits 12-lipoxygenase (h12-LOX), making it useful in the study of metabolic and cardiovascular diseases. Furthermore, it activates the sulfonylurea receptor 1 (SUR1) associated with the ATP-sensitive potassium channel Kir6.2, playing a role in regulating insulin secretion and blood glucose levels. As a substrate, it participates in cholesterol esterification catalyzed by acyl-coenzyme A:cholesterol acyltransferase 1 (ACAT1).
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| ln Vitro |
In cell-free systems, Oleoyl coenzyme A lithium exhibits multiple biological activities. Studies have shown that at a concentration of 1 μM, it activates the SUR1 receptor associated with the Kir6.2 channel in Xenopus oocytes. As a substrate for ACAT1, it is used to assess cholesterol esterification activity in vitro. As a potent allosteric inhibitor of h15-LOX-2, it modulates lipid peroxidation processes. Additionally, as a key intermediate in fatty acid metabolism, it participates in mitochondrial beta-oxidation to provide energy for cells.
In Xenopus oocytes, oleoyl-CoA (1 μM) activates sulfonylurea receptor 1 (SUR1), which is connected to the ATP-sensitive potassium channel Kir6.2 [2]. |
| ln Vivo |
In vivo activity data for directly administered Oleoyl coenzyme A lithium is limited. In vivo evidence primarily comes from studies on its precursor, oleic acid, or related metabolic pathways. As an endogenous metabolite in E. coli and mice, it participates in lipid synthesis and catabolism in vivo. In metabolic regulation, changes in Oleoyl-CoA levels can influence gene expression and the activity of proteins involved in lipid metabolism, such as regulating the balance between free cholesterol and cholesterol esters in the cholesterol metabolism pathway. In plants, similar molecules have been reported to mediate the nuclear translocation of hypoxia response factors.
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| Enzyme Assay |
Oleoyl coenzyme A lithium is used as a substrate for acyltransferase activity assays in cell-free systems. A typical protocol (using ACAT1): Microsomes are isolated from the livers of cholesterol-fed rats. The microsomes are incubated with [1-¹⁴C]-labeled Oleoyl-CoA (as the acyl donor) and exogenous cholesterol in potassium phosphate buffer (pH 7.4) at 37°C. After the reaction, cholesterol esters are extracted using organic solvents, and radioactivity is measured using a liquid scintillation counter to quantify ACAT1 enzyme activity. For lipoxygenase inhibition assays, the inhibition constant is assessed by monitoring the formation of specific products.
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| Cell Assay |
Due to its high polarity and membrane impermeability, Oleoyl coenzyme A lithium is typically studied in cellular assays using permeabilized cell models or indirect approaches with its precursor. A typical protocol (ACAT activity assay): Microsomes are isolated from treated cells (e.g., macrophages) and incubated with [1-¹⁴C]Oleoyl-CoA. Intracellular ACAT activity is assessed by measuring the formation of radiolabeled cholesterol esters. In ion channel studies, patch-clamp techniques can be used: Oleoyl-CoA (1 μM) is applied to the extracellular side of cells expressing SUR1/Kir6.2 channels via a perfusion system, and changes in channel current are recorded to evaluate its activating effect.
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| Animal Protocol |
Oleoyl coenzyme A lithium itself is rarely administered directly to animals; studies typically use its precursor oleic acid or genetic knockout models. In metabolic studies, labeled oleic acid can be administered via tail vein injection or gavage, with tissue samples collected at various time points for LC-MS/MS analysis of Oleoyl-CoA and its metabolites. Long-chain acyl-CoA synthetase knockout mouse models can also be used to study the physiological impact of Oleoyl-CoA metabolic dysregulation on lipid metabolism in the liver and adipose tissue. For assessing lipoxygenase inhibitory activity, animal models of inflammation or metabolic disease can be used, administering the compound orally or intraperitoneally, followed by detection of inflammatory markers and lipid peroxides in tissues.
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| ADME/Pharmacokinetics |
Direct pharmacokinetic parameters for Oleoyl coenzyme A lithium are limited in the literature as it is an endogenous intracellular metabolite. As a highly polar molecule carrying strong negative charges at physiological pH, it cannot passively diffuse across cell membranes and is primarily synthesized intracellularly and utilized within organelles such as mitochondria and the endoplasmic reticulum. It is unstable in plasma and susceptible to hydrolysis by esterases. Tissue concentrations of Oleoyl-CoA are tightly regulated by fatty acid metabolic status and can change significantly under conditions such as starvation or diabetes. Exogenous Oleoyl-CoA lithium cannot readily enter intact cells and typically requires delivery systems (e.g., formulation with cyclodextrins, liposomes) or co-solvents such as DMSO/PEG300 for in vivo administration. For storage, it should be kept dry and sealed at -20°C or -80°C, avoiding repeated freeze-thaw cycles.
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| Toxicity/Toxicokinetics |
Oleoyl coenzyme A lithium is generally considered safe at normal physiological concentrations as an endogenous metabolite. According to available Material Safety Data Sheets, no detailed toxicological data has been reported for this compound. Suppliers warn that this product is for research use only and not for human or veterinary use. As a chemical reagent, it is recommended to wear personal protective equipment (e.g., gloves and eye protection) to avoid skin and eye contact, and to operate in a well-ventilated area. At high concentrations, it may cause long-lasting harmful effects to aquatic life. Under conditions of metabolic dysregulation (e.g., obesity, diabetes), abnormal accumulation of Oleoyl-CoA may contribute to lipotoxic pathological processes.
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| References |
[1]. Human acyl-CoA dehydrogenase-9 plays a novel role in the mitochondrial beta-oxidation of unsaturated fatty acids. J Biol Chem. 2005 Sep 16;280(37):32309-16.
[2]. Mechanism of cloned ATP-sensitive potassium channel activation by oleoyl-CoA. J Biol Chem. 1998 Oct 9;273(41):26383-7. |
| Molecular Formula |
C39H68N7O17P3S.LI
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|---|---|
| Molecular Weight |
1031.98032
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| Exact Mass |
1055.39
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| CAS # |
188824-37-5
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| Related CAS # |
Oleoyl Coenzyme A;1716-06-9
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| PubChem CID |
117072678
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| Appearance |
White to off-white solid powder
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| LogP |
7.585
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
34
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| Heavy Atom Count |
71
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| Complexity |
1680
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| Defined Atom Stereocenter Count |
5
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| SMILES |
CCCCCCCC/C=C/CCCCCCCC(SCCNC(CCNC(C(C(COP(OP(OCC1OC(N2C=NC3=C(N=CN=C23)N)C(O)C1OP(=O)(O)O)(O)=O)(O)=O)(C)C)O)=O)=O)=O
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| InChi Key |
OITFSDVCTCHDHP-FGBQLYJKSA-J
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| InChi Code |
InChI=1S/C39H68N7O17P3S.4Li/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46;;;;/h11-12,26-28,32-34,38,49-50H,4-10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54);;;;/q;4*+1/p-4/b12-11-;;;;/t28-,32-,33-,34+,38-;;;;/m1..../s1
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| Chemical Name |
tetralithium;[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-[[3-[2-[(Z)-octadec-9-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate
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| Synonyms |
Oleoyl coenzyme A lithium salt; 188824-37-5; tetralithium;[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[[[[(3R)-3-hydroxy-2,2-dimethyl-4-[[3-[2-[(Z)-octadec-9-enoyl]sulfanylethylamino]-3-oxopropyl]amino]-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]oxolan-3-yl] phosphate; cis-9-octadecenoyl coenzyme a lithium salt; Oleoyl coenzyme A (lithium);
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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: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| 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) |
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
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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 | 0.9690 mL | 4.8451 mL | 9.6901 mL | |
| 5 mM | 0.1938 mL | 0.9690 mL | 1.9380 mL | |
| 10 mM | 0.0969 mL | 0.4845 mL | 0.9690 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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