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L-Octanoylcarnitine

Cat No.:V31204 Purity: ≥98%
L-Octanoylcarnitine is a plasma metabolite and is the physiologically active form of octanoylcarnitine.
L-Octanoylcarnitine
L-Octanoylcarnitine Chemical Structure CAS No.: 25243-95-2
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
100mg
Other Sizes

Other Forms of L-Octanoylcarnitine:

  • Octanoylcarnitine chloride ((±)-octanoylcarnitine chloride)
  • L-Octanoylcarnitine hydrochloride
  • L-Octanoylcarnitine-d3
  • L-Octanoylcarnitine-d3 hydrochloride
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
L-Octanoylcarnitine is a plasma metabolite and is the physiologically active form of octanoylcarnitine. L-Octanoylcarnitine may be utilized in breast cancer research.
L-Octanoylcarnitine (CAS 25243-95-2) is a physiologically active form of octanoylcarnitine and a plasma metabolite. It is an endogenous metabolite involved in fatty acid metabolism, specifically in the transport of fatty acids into mitochondria for beta-oxidation. L-Octanoylcarnitine is formed by the esterification of carnitine with octanoic acid (a medium-chain fatty acid). It plays a crucial role in energy metabolism and is detected in medium-chain acyl-CoA dehydrogenase (MCAD) deficiency, a metabolic disorder characterized by intolerance to prolonged fasting and recurrent episodes of hypoglycemic coma. L-Octanoylcarnitine has also attracted research interest as a potential biomarker for breast cancer.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary biological targets of L-octanoylcarnitine are the enzymes and proteins involved in fatty acid metabolism. It interacts with medium-chain acyl-CoA dehydrogenase (MCAD), which catalyzes the initial step in the beta-oxidation of medium-chain fatty acids. As a carnitine ester, L-octanoylcarnitine is involved in the carnitine shuttle system, which transports fatty acids from the cytosol into the mitochondrial matrix for beta-oxidation. It may also interact with carnitine palmitoyltransferase 1 (CPT1) and carnitine-acylcarnitine translocase. Additionally, L-octanoylcarnitine has been studied as a potential biomarker for breast cancer, indicating its involvement in cancer metabolism.
ln Vitro
L-Octanoylcarnitine (0.2 mM) stimulates H2O2 release from scaffolding mitochondria (RLM) [2].
In vitro, L-octanoylcarnitine has been shown to modulate mitochondrial activity. At millimolar concentrations, it induces hydrogen peroxide (H2O2) release from rat liver mitochondria. This effect is concentration-dependent, with 0.2 mM L-octanoylcarnitine stimulating H2O2 release from scaffolding mitochondria. The compound's ability to induce mitochondrial ROS production may have implications for cellular signaling and oxidative stress. L-Octanoylcarnitine has also been studied in the context of breast cancer research, where it may serve as a potential biomarker for the disease. Its role in fatty acid metabolism makes it a useful tool for studying metabolic pathways in vitro.
ln Vivo
L-octanoylcarnitine lowers nasal membrane and detrusor strength during high-fat diet (HFD) action-blood flow respiration and respiratory conductance [3].
In vivo, L-octanoylcarnitine is an endogenous metabolite present in plasma. It has been shown to lower nasal membrane and detrusor strength during high-fat diet (HFD) action-blood flow respiration and respiratory conductance. As a physiologically active form of octanoylcarnitine, it plays a role in fatty acid metabolism and energy homeostasis. It is detected in MCAD deficiency, where its levels are elevated due to impaired fatty acid oxidation. L-Octanoylcarnitine may also be involved in the metabolic alterations associated with breast cancer, making it a potential biomarker for the disease. Its in vivo effects are related to its role in fatty acid transport and mitochondrial function.
Enzyme Assay
L-Octanoylcarnitine, as a small molecule metabolite, does not typically undergo classical enzyme/receptor binding assays. However, its interaction with MCAD can be studied using enzyme activity assays. A typical protocol involves incubating L-octanoylcarnitine with purified MCAD enzyme and measuring the production of octanoyl-CoA or the reduction of electron transfer flavoprotein (ETF) using spectrophotometric methods. The reaction mixture contains MCAD, L-octanoylcarnitine, CoA, and an electron acceptor such as ferricenium hexafluorophosphate. The rate of reaction is monitored by measuring the change in absorbance at a specific wavelength. The kinetic parameters (Km and Vmax) can be determined by varying the substrate concentration.
Cell Assay
For in vitro cellular experiments, cells (e.g., hepatocytes, cancer cell lines, or primary cells) are cultured in appropriate media and treated with L-octanoylcarnitine at various concentrations (typically 0.1-1 mM). After treatment, cells are harvested and analyzed for various endpoints. For studies on mitochondrial function, mitochondrial ROS production can be measured using fluorescent probes such as DCFH-DA or MitoSOX. For studies on fatty acid metabolism, the rate of fatty acid oxidation can be measured by incubating cells with radiolabeled fatty acids and monitoring the production of CO2 or acid-soluble metabolites. The duration of treatment varies depending on the experimental design but typically ranges from 1 to 24 hours.
Animal Protocol
In vivo animal experiments with L-octanoylcarnitine are not typically performed due to its role as an endogenous metabolite. However, its levels can be measured in animal models of metabolic diseases. For example, in mouse models of MCAD deficiency or high-fat diet-induced obesity, plasma L-octanoylcarnitine levels can be measured by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The compound can also be administered exogenously to study its effects on metabolism. Dosing regimens and routes of administration vary depending on the experimental objectives. Blood and tissue samples are collected for metabolomic analysis.
ADME/Pharmacokinetics
L-Octanoylcarnitine is an endogenous metabolite with a molecular weight of 287.4 g/mol and a molecular formula of C15H29NO4. It is soluble in DMSO and should be stored at -20degC. As an endogenous compound, its pharmacokinetic properties are governed by normal metabolic processes. It is synthesized in the body from carnitine and octanoic acid and is involved in fatty acid transport and oxidation. L-Octanoylcarnitine is present in plasma and other biological fluids. Its levels can be altered in metabolic disorders such as MCAD deficiency. Exogenous administration of L-octanoylcarnitine would be subject to normal metabolic turnover and clearance.
Toxicity/Toxicokinetics
L-Octanoylcarnitine is an endogenous metabolite and is generally considered safe at physiological concentrations. However, elevated levels of L-octanoylcarnitine are associated with metabolic disorders such as MCAD deficiency, indicating that abnormal accumulation can be pathological. In vitro studies have shown that L-octanoylcarnitine at millimolar concentrations can induce mitochondrial ROS production, which may contribute to oxidative stress. At lower, physiologically relevant concentrations, the compound is not considered toxic. As a research compound, L-octanoylcarnitine should be handled with standard laboratory precautions. It is for research use only and not for human therapeutic use.
References

[1]. Association between arterial stiffness and serum L-octanoylcarnitine and lactosylceramide in overweight middle-aged subjects: 3-year follow-up study. PLoS One. 2015 Mar 17;10(3):e0119519.

[2]. Schönfeld P, Reiser G. Inhibition of β-oxidation is not a valid therapeutic tool for reducing oxidative stress in conditions of neurodegeneration. J Cereb Blood Flow Metab. 2017 Mar;37(3):848-854.

[3]. CHRONIC HIGH FAT DIET IMPAIRS DETRUSOR MITOCHONDRIAL FATTY ACID OXIDATION IN MALE BUT NOT FEMALE MICE. Journal of UrologyBladder & Urethra: Anatomy, Physiology & Pharmacology I (MP11)1 Apr 2019.

Additional Infomation
O-O-capryl-L-carnitine is the L-enantiomer of O-capryl carnitine and plays a role in human metabolism. It is an O-capryl carnitine, as well as a saturated fatty acyl-L-carnitine and a medium-chain fatty acyl-L-carnitine. It is the enantiomer of O-capryl-D-carnitine. L-capryl carnitine has been reported to be detected in both Homo sapiens and Euglena, with relevant data available. See also: Capryl carnitine (note moved to).
L-Octanoylcarnitine is the physiologically active form of octanoylcarnitine and is a plasma metabolite. It is a medium-chain acylcarnitine formed by the esterification of carnitine with octanoic acid. L-Octanoylcarnitine plays a crucial role in the transport of fatty acids into mitochondria for beta-oxidation. It is detected in MCAD deficiency, a metabolic disorder characterized by impaired oxidation of medium-chain fatty acids. L-Octanoylcarnitine has also been identified as a potential biomarker for breast cancer. Its levels in plasma may reflect alterations in fatty acid metabolism associated with cancer. The compound is available as a research chemical and is used in studies of metabolism, mitochondrial function, and cancer biology.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H29NO4
Molecular Weight
287.39506
Exact Mass
287.21
CAS #
25243-95-2
Related CAS #
Octanoylcarnitine chloride;14919-35-8;L-Octanoylcarnitine hydrochloride;54377-02-5;L-Octanoylcarnitine-d3;204259-56-3
PubChem CID
11953814
Appearance
White to off-white solid powder
LogP
1.104
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
11
Heavy Atom Count
20
Complexity
291
Defined Atom Stereocenter Count
1
SMILES
CCCCCCCC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
InChi Key
CXTATJFJDMJMIY-CYBMUJFWSA-N
InChi Code
InChI=1S/C15H29NO4/c1-5-6-7-8-9-10-15(19)20-13(11-14(17)18)12-16(2,3)4/h13H,5-12H2,1-4H3/t13-/m1/s1
Chemical Name
(3R)-3-octanoyloxy-4-(trimethylazaniumyl)butanoate
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 Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~347.95 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 0.5 mg/mL (1.74 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 5.0 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: ≥ 0.5 mg/mL (1.74 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in 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 5.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 0.5 mg/mL (1.74 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 5.0 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 3.4795 mL 17.3974 mL 34.7947 mL
5 mM 0.6959 mL 3.4795 mL 6.9589 mL
10 mM 0.3479 mL 1.7397 mL 3.4795 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.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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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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