| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
The primary targets of Oleoyl Coenzyme A triammonium include neutral lipase and the transcription factor RAP2.12 in plants. It regulates lipid metabolism by inhibiting the activity of neutral lipase. In plants (e.g., Arabidopsis thaliana), this compound mediates ATP-dependent signal transduction pathways by activating the translocation of the transcription factor RAP2.12 from the plasma membrane to the nucleus, thereby regulating the expression of genes involved in the hypoxic response. Additionally, as a long-chain fatty acyl-CoA, it serves as a substrate for various acyltransferases (e.g., ACAT), participating in cholesterol esterification and fatty acid metabolism.
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| ln Vitro |
In cell-free systems, Oleoyl Coenzyme A triammonium exhibits inhibitory effects on neutral lipase. As a fatty acyl-CoA, it serves as an acyl donor in various in vitro enzymatic reactions, such as a substrate in ACAT (acyl-CoA:cholesterol acyltransferase) activity assays to assess cholesterol ester formation. Furthermore, in neutral lipase inhibition assays derived from plant sources, Oleoyl-CoA effectively inhibits the hydrolysis of storage lipids in lipid bodies, indicating its critical role in regulating lipid metabolism.
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| ln Vivo |
In vivo activity studies of Oleoyl Coenzyme A triammonium are primarily derived from plant models. In Arabidopsis thaliana, this compound regulates the expression of hypoxia-responsive genes by activating the translocation of the transcription factor RAP2.12 from the plasma membrane to the nucleus. This process is ATP-dependent; under hypoxic conditions, changes in Oleoyl-CoA levels trigger the nuclear translocation of RAP2.12, initiating the transcription of downstream genes to help the plant adapt to hypoxia. In animals, the activity of this compound is primarily studied indirectly through its precursor oleic acid or related metabolic pathways, where it participates in the regulation of fatty acid metabolism and energy production.
Oleoyl coenzyme A triammonium activates the translocation of the transcription factor RAP2.12 from the plasma membrane to the nucleus in Arabidopsis thaliana and regulates the expression of related genes under hypoxic conditions[1]. |
| Enzyme Assay |
Oleoyl Coenzyme A triammonium can be used for in vitro assays of neutral lipase inhibitory activity. A typical protocol involves purifying neutral lipase from plant lipid bodies (e.g., castor bean), incubating the enzyme with Oleoyl-CoA in a suitable buffer (e.g., Tris-HCl, pH 7.5) using a triolein emulsion as the substrate. After the reaction, enzyme activity is assessed by measuring the release of free fatty acids (e.g., using colorimetric methods or radiolabeled substrates). The inhibitory effect of Oleoyl-CoA can be characterized by measuring changes in enzyme activity at varying concentrations. For ACAT activity assays, rat liver microsomes are incubated with [1-¹⁴C]-labeled Oleoyl-CoA, and cholesterol ester formation is detected by radioactivity counting.
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| Cell Assay |
Due to the high polarity and membrane impermeability of Oleoyl-CoA triammonium, in vitro cellular assays typically utilize permeabilized cell models or indirect approaches using its precursor. A typical protocol (for plant cells): Isolate Arabidopsis protoplasts, incubate them with Oleoyl-CoA (e.g., 10-100 μM), and observe the nuclear translocation of fluorescently labeled RAP2.12 protein by microscopy. For animal cell studies, microsomal fractions derived from macrophages can be incubated with Oleoyl-CoA to assess ACAT activity by detecting radiolabeled cholesterol ester formation. Alternatively, liposome transfection or cell-penetrating peptide-assisted delivery can be used to introduce Oleoyl-CoA into cells.
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| Animal Protocol |
Oleoyl Coenzyme A triammonium 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 (e.g., liver, adipose tissue) 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. For in vivo assessment of lipase inhibitory activity, high-fat diet-induced obese mouse models can be used, administering the compound intraperitoneally or intravenously, followed by detection of tissue triglyceride levels and lipase activity changes.
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| ADME/Pharmacokinetics |
Direct pharmacokinetic parameters for Oleoyl Coenzyme A triammonium are limited in the literature as it is an endogenous intracellular metabolite. As a highly polar molecule (LogP approx. 7.94) carrying strong negative charges under physiological conditions, 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 triammonium cannot readily enter intact cells and typically requires delivery systems or the use of its precursor for in vivo studies. For storage, the powder 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 triammonium 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, such as inducing endoplasmic reticulum stress and mitochondrial dysfunction.
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| References |
| Molecular Formula |
C39H71N8O17P3S
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|---|---|
| Molecular Weight |
1049.0107319355
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| CAS # |
799812-89-8
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| Appearance |
Typically exists as solids at room temperature
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| LogP |
7.936
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| SMILES |
S(CCNC(CCNC([C@@H](C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3C(N)=NC=NC2=3)O1)O)OP(=O)(O)O)O)=O)=O)C(CCCCCCC/C=C\CCCCCCCC)=O.N
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| Synonyms |
Oleoyl Coenzyme A Ammonium Salt; Coenzyme A, S-(9Z)-9-octadecenoate, triammonium salt; S-[2-[3-[[(2R)-4-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-2-hydroxy-3,3-dimethylbutanoyl]amino]propanoylamino]ethyl] (Z)-octadec-9-enethioate;azane; CoenzymeA,S-(9Z)-9-octadecenoate,triammoniumsalt
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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) |
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 | 0.9533 mL | 4.7664 mL | 9.5328 mL | |
| 5 mM | 0.1907 mL | 0.9533 mL | 1.9066 mL | |
| 10 mM | 0.0953 mL | 0.4766 mL | 0.9533 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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