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Decanoyllevocarnitine

Alias: (-)-Decanoylcarnitine; Decanoyllevocarnitine
Cat No.:V26169 Purity: ≥98%
Decanoyl-L-carnitine promotes the formation of saturated fatty acid metabolites.
Decanoyllevocarnitine
Decanoyllevocarnitine Chemical Structure CAS No.: 3992-45-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Decanoyl-L-carnitine promotes the formation of saturated fatty acid metabolites.
Decanoylevocarnitine (CAS#: 3992-45-8), also known as O-decanoyl-L-carnitine, is an ester analogue of L-carnitine. It is an O-acyl-L-carnitine, specifically an L-carnitine with a decanoyl (C10:0) group as the acyl substituent. It is a naturally occurring human metabolite and an endogenous medium-chain acylcarnitine. Decanoylevocarnitine plays a crucial role in energy metabolism by facilitating the transport of medium-chain fatty acids into the mitochondria for β-oxidation via the carnitine shuttle. It is used as a research tool to study fatty acid metabolism and as a potential biomarker for metabolic disorders.
Biological Activity I Assay Protocols (From Reference)
Targets
Decanoylevocarnitine targets the mitochondrial fatty acid oxidation pathway. It functions as an acylcarnitine that transports medium-chain fatty acids, like decanoate, into the mitochondrial matrix for β-oxidation via the carnitine shuttle. By facilitating fatty acid entry into the mitochondria, it plays a central role in energy metabolism. Its levels are associated with altered energy metabolism and mitochondrial dysfunction in conditions such as insulin resistance and heart failure.
ln Vitro
In vitro, decanoylevocarnitine has a stimulatory effect on the formation of desaturated fatty acid metabolites from both [1-14C]-22:4 (n-6) and [1-14C]-22:5 (n-3). It increases the formation of C24 fatty acid intermediates, as well as docosapentaenoic and docosahexaenoic acid in rat hepatocytes. It is used in studies to assess fatty acid oxidation and as a standard in analytical methods for detecting acylcarnitines.
ln Vivo
In vivo, decanoylevocarnitine is a normal metabolite present in the body. Abnormal increases in decanoylevocarnitine in rodent models are associated with reduced cardiac efficiency and impaired glucose utilization, supporting its role as both a metabolic intermediate and a pathophysiological indicator. It accumulates in models of impaired β-oxidation, insulin resistance, and heart failure, where elevated plasma and tissue levels correlate with altered energy metabolism and mitochondrial dysfunction.
Enzyme Assay
In vitro assays for decanoylevocarnitine are typically analytical, using methods like mass spectrometry to measure its levels. It can be used as a substrate or standard in enzyme assays to study the activity of enzymes involved in fatty acid metabolism, such as carnitine palmitoyltransferase. Its effects on fatty acid desaturation can be assessed by incubating rat hepatocytes with radiolabeled fatty acid precursors and measuring the formation of desaturated metabolites.
Cell Assay
For cell-based studies, decanoylevocarnitine can be added to the culture medium of hepatocytes or other cell lines to study its effects on fatty acid oxidation and metabolism. Cells are treated with the compound at various concentrations, and the formation of fatty acid metabolites is measured using radiometric or chromatographic methods. It is also used as a supplement in cell culture media for metabolic studies.
Animal Protocol
In vivo, decanoylevocarnitine is a naturally occurring metabolite. It is not typically administered as a therapeutic agent in animal studies but is measured as a biomarker. In rodent models of metabolic disorders, plasma and tissue levels of decanoylevocarnitine are quantified to assess alterations in fatty acid oxidation and mitochondrial function.
ADME/Pharmacokinetics
Decanoylevocarnitine (MW 315.45, C₁₇H₃₃NO₄) is a medium-chain acylcarnitine. It is a white to off-white solid powder. The compound is soluble in DMSO (100 mg/mL). It is typically stored as a powder at -20°C for long-term stability. Detailed pharmacokinetic parameters are not extensively reported as it is an endogenous metabolite.
Toxicity/Toxicokinetics
Decanoylevocarnitine is an endogenous metabolite and is generally considered to be safe at normal physiological levels. However, elevated levels are associated with metabolic disorders and may indicate mitochondrial dysfunction. It is for research use only and is not intended for human therapeutic applications.
References

[1]. Differences in the conversion of the polyunsaturated fatty acids [1-(14)C]22:4(n-6) and [1-(14)C]22:5(n-3) to [(14)C]22:5(n-6) and [(14)C]22:6(n-3) in isolated rat hepatocytes. Biochim Biophys Acta. 2001 May 31;1532(1-2):137-47.

[2]. Phospholipid Levels at Seroconversion Are Associated With Resolution of Persistent Islet Autoimmunity: The Diabetes Autoimmunity Study in the Young.Diabetes.

Additional Infomation
O-decanoyl-L-carnitine is an O-acyl-L-carnitine, specifically an L-carnitine with a decanoyl group as the acyl substituent. It is a human metabolite. It is an O-decanoylcarnitine, and also a saturated fatty acyl-L-carnitine and a medium-chain fatty acyl-L-carnitine. It has been reported that O-decanoyl-L-carnitine is present in the Chinese honeybee (Apis cerana), and relevant data exists.
Decanoylevocarnitine is a research compound used to study fatty acid metabolism and as a potential biomarker for metabolic disorders. It is not a drug and has no clinical applications. It is commercially available from various chemical suppliers for research purposes only. Its role in the carnitine shuttle makes it a valuable tool for investigating energy metabolism and mitochondrial function.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H33NO4
Molecular Weight
315.45
Exact Mass
315.24
CAS #
3992-45-8
PubChem CID
11953821
Appearance
White to off-white solid powder
LogP
0.1
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
13
Heavy Atom Count
22
Complexity
318
Defined Atom Stereocenter Count
1
SMILES
CCCCCCCCCC(=O)O[C@H](CC(=O)[O-])C[N+](C)(C)C
InChi Key
LZOSYCMHQXPBFU-OAHLLOKOSA-N
InChi Code
InChI=1S/C17H33NO4/c1-5-6-7-8-9-10-11-12-17(21)22-15(13-16(19)20)14-18(2,3)4/h15H,5-14H2,1-4H3/t15-/m1/s1
Chemical Name
(3R)-3-decanoyloxy-4-(trimethylazaniumyl)butanoate
Synonyms
(-)-Decanoylcarnitine; Decanoyllevocarnitine
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 (~317.01 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.93 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 (7.93 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 25.0 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: ≥ 2.5 mg/mL (7.93 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 3.1701 mL 15.8504 mL 31.7007 mL
5 mM 0.6340 mL 3.1701 mL 6.3401 mL
10 mM 0.3170 mL 1.5850 mL 3.1701 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 is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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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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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)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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