| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
Linoleoyl-coenzyme A is a novel and potent bioactive compound
Linoleoyl-coenzyme A (Linoleoyl-CoA; CAS: 40757-80-0) is the thioester derivative of coenzyme A and linoleic acid, an omega-6 polyunsaturated C18:2 fatty acid. It is an endogenous metabolic intermediate with the chemical formula C₃₉H₆₆N₇O₁₇P₃S and a molecular weight of approximately 1030 Da. As a natural metabolite in both mice and humans, it plays a central role in fatty acid β-oxidation, lipid synthesis, and cellular signal transduction.| Targets |
The targets of Linoleoyl-CoA include various enzymes and transcriptional regulators. It serves as a substrate for acyl-CoA dehydrogenase-9 (ACAD-9), which exhibits maximal activity with long-chain unsaturated acyl-CoAs, catalyzing the first step of mitochondrial fatty acid β-oxidation. It binds to and inhibits the activity of glutathione S-transferase 1 (GST1). In liver plasma membranes, it modulates adenylate cyclase activity upon incorporation into membrane phospholipids, enhancing basal, fluoride-, and glucagon-stimulated enzyme activities. Additionally, it is a substrate for diacylglycerol acyltransferase (DGAT) in triglyceride synthesis.
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| ln Vitro |
In cell-free systems, Linoleoyl-CoA functions as a substrate or modulator for various enzymes. In ACAD-9 activity assays, Linoleoyl-CoA is among the best substrates, exhibiting higher oxidation rates compared to other long-chain acyl-CoAs. In rat liver plasma membrane preparations, linoleate (which forms Linoleoyl-CoA upon incorporation into membrane phospholipids) enhances basal, fluoride-stimulated, and glucagon-stimulated adenylate cyclase activities, whereas oleoyl-CoA shows no such effect, indicating a specific regulatory role for linoleate. In DGAT activity assays, 50 μM Linoleoyl-CoA serves as the acyl donor for assessing triglyceride synthesis.
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| ln Vivo |
In vivo activity data for directly administered Linoleoyl-CoA is limited. As an endogenous metabolite, it participates in the pathogenesis of obesity and type 2 diabetes: inhibition of the mitochondrial adenine nucleotide translocator by long-chain acyl-CoAs is proposed to underlie the mechanism linking obesity and type 2 diabetes. In vivo, the oxidation of unsaturated fatty acids (including linoleate) is catalyzed by ACADs, with ACAD-9 exhibiting maximal activity with long-chain unsaturated substrates such as Linoleoyl-CoA. Linoleate also regulates the proinflammatory cytokine IL8 via the JNK and nuclear factor kappa B pathways.
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| Enzyme Assay |
Linoleoyl-CoA can be used as a substrate for acyl-CoA dehydrogenase activity assays. A typical protocol (ACAD-9 assay): The reaction mixture contains 50 mM potassium phosphate buffer (pH 7.5), 100 μM Linoleoyl-CoA, 0.2 mM electron transfer flavoprotein (ETF), and purified ACAD-9 enzyme. Activity is measured by monitoring the fluorescence reduction of ETF at 340 nm excitation and 480 nm emission. For DGAT assay: 60 μg of purified enzyme, 100 μM 1,2-dioleoyl-sn-glycerol, and 50 μM Linoleoyl-CoA are incubated in 100 mM phosphate buffer (pH 8.0), with products separated by HPTLC and visualized.
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| Cell Assay |
Due to the high polarity (polar surface area of 418 Ų) and membrane impermeability of Linoleoyl-CoA, cellular assays typically use its precursor linoleic acid for indirect studies. A typical protocol (adenylate cyclase assay): Isolated rat hepatocytes are incubated with linoleic acid (which is converted intracellularly to Linoleoyl-CoA and incorporated into membrane phospholipids). Plasma membranes are then prepared, and adenylate cyclase activities (basal, fluoride-stimulated, and glucagon-stimulated) are measured by detecting the conversion of [α-³²P]ATP to cAMP.
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| Animal Protocol |
Linoleoyl-CoA itself is rarely administered directly to animals; studies typically use its precursor linoleic acid or genetically modified models. In metabolic studies, labeled linoleic acid can be administered via gavage or tail vein injection, with tissue samples (e.g., liver, adipose tissue) collected at various time points for LC-MS/MS analysis of Linoleoyl-CoA and its metabolites. ACAD-9 knockout mouse models can also be used to study the impact of Linoleoyl-CoA metabolic dysregulation on fatty acid β-oxidation and energy metabolism. For lipid metabolism regulation studies, high-fat diet-induced obese mouse models can be used, administering linoleic acid followed by detection of inflammatory markers and lipid peroxides in tissues.
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| ADME/Pharmacokinetics |
Direct pharmacokinetic parameters for Linoleoyl-CoA are limited in the literature as it is an endogenous intracellular metabolite. As a highly polar molecule (LogD pH 7.4 ≈ -5.18), it carries strong negative charges at physiological pH (tetra-anion form) and cannot passively diffuse across cell membranes. It is primarily synthesized intracellularly and utilized within mitochondria, with tissue concentrations tightly regulated by fatty acid metabolic status. It is unstable in plasma and susceptible to hydrolysis by esterases. Exogenous Linoleoyl-CoA cannot readily enter intact cells, necessitating the use of its precursor linoleic acid for in vitro and in vivo studies. 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 |
Linoleoyl-CoA 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 to avoid skin and eye contact and to operate in a well-ventilated area. Under conditions of metabolic dysregulation (e.g., obesity, type 2 diabetes), abnormal accumulation of long-chain acyl-CoAs (including Linoleoyl-CoA) may contribute to lipotoxic pathological processes by inhibiting the adenine nucleotide translocator, leading to mitochondrial dysfunction.
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| References |
[1]. https://pubchem.ncbi.nlm.nih.gov/compound/170421
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| Molecular Formula |
C39H66N7O17P3S
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| Molecular Weight |
1046.97
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| Exact Mass |
1029.34
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| Elemental Analysis |
C, 44.74; H, 6.45; N, 9.36; O, 27.51; P, 8.88; S, 3.06
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| CAS # |
40757-80-0
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| PubChem CID |
6441626
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| Appearance |
Typically exists as solid at room temperature
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| LogP |
6.74
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
22
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| Rotatable Bond Count |
34
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| Heavy Atom Count |
67
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| Complexity |
1750
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C(SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(N2C3=C(C(=NC=N3)N)N=C2)C(O)C1OP(O)(O)=O)(=O)CCCCCCC/C=C/C/C=C/CCCCC
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| InChi Key |
YECLLIMZHNYFCK-RQHJKPPISA-N
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| InChi Code |
InChI=1S/C39H66N7O17P3S/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/h8-9,11-12,26-28,32-34,38,49-50H,4-7,10,13-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8+,12-11+/t28-,32-,33-,34+,38-/m1/s1
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| Chemical Name |
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] (9E,12E)-octadeca-9,12-dienethioate
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| Synonyms |
DTXSID301295158; Coenzyme A, S-9,12-octadecadienoate; RefChem:1082104; DTXCID501725688; 40757-80-0; Coenzyme A, linoleoyl- Linoleoyl-coenzyme A
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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 | 0.9551 mL | 4.7757 mL | 9.5514 mL | |
| 5 mM | 0.1910 mL | 0.9551 mL | 1.9103 mL | |
| 10 mM | 0.0955 mL | 0.4776 mL | 0.9551 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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