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Dioctanoylglycol

Cat No.:V49827 Purity: ≥98%
Dioctanoylglycol (Ethylene glycol dicaprylate) is a diacylglycerol analog and an inhibitor (blocker/antagonist) of diacylglycerol kinase (DGK) (Ki 58 μM).
Dioctanoylglycol
Dioctanoylglycol Chemical Structure CAS No.: 627-86-1
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Dioctanoylglycol (Ethylene glycol dicaprylate) is a diacylglycerol analog and an inhibitor (blocker/antagonist) of diacylglycerol kinase (DGK) (Ki 58 μM).
Dioctanoylglycol (CAS#: 627-86-1) is a glycolipid compound with a molecular formula of C18H34O4 and a molecular weight of 314.46. It is a diester of ethylene glycol and octanoic acid. Dioctanoylglycol is used in research on lipid metabolism and as a component in the formulation of lipid-based drug delivery systems. The compound is available in high purity for research use.
Biological Activity I Assay Protocols (From Reference)
Targets
Dioctanoylglycol does not have a specific biological target but functions as a lipid excipient. As a glycolipid, it can be incorporated into lipid-based formulations to improve the solubility and delivery of lipophilic drugs. Its structure, consisting of a hydrophilic ethylene glycol linker and two lipophilic octanoic acid chains, allows it to act as a surfactant and emulsifier. Its role is primarily formulation-based rather than pharmacologically active.
ln Vitro
Dioctanoylglycerol (dioctanoylglycerol) creates a longer-lasting diacylglycerol signal in platelets by inhibiting diacylglycerol phosphorylation (70–100% at 100 μM) [1].
In vitro, dioctanoylglycol is used in the preparation and characterization of lipid-based drug delivery systems. The compound's physical and chemical properties, including its solubility and compatibility with other lipids, are characterized for formulation development. The compound is not typically used in pharmacological activity assays but rather in studies of formulation stability, drug release, and cellular uptake of lipid-based carriers.
ln Vivo
In vivo, dioctanoylglycol is used as a component of lipid-based formulations for drug delivery. The compound's in vivo behavior is formulation-dependent, and its role is to provide structural integrity and stability to the formulations. When administered, the lipid components are metabolized by esterases, releasing the constituent fatty acids. Its in vivo effects are related to the delivered drug rather than the lipid itself.
Enzyme Assay
The in vitro assays for dioctanoylglycol typically involve formulation characterization. Lipid-based formulations containing the compound are prepared using standard methods. Particle size is measured by dynamic light scattering (DLS), and drug encapsulation efficiency is determined. Drug release kinetics are assessed by dialysis. Stability studies are performed by monitoring particle size and drug leakage over time. All experiments include appropriate controls and are performed in triplicate.
Cell Assay
For in vitro cellular assays, lipid-based formulations containing dioctanoylglycol are incubated with cultured cells at varying lipid concentrations. Cellular uptake is assessed using fluorescently labeled lipids or encapsulated fluorescent markers by flow cytometry or confocal microscopy. Cytotoxicity is evaluated using MTT or CellTiter-Glo assays. For drug delivery studies, the efficacy of encapsulated drugs is compared to free drug controls. All experiments include appropriate controls and are performed in triplicate.
Animal Protocol
For in vivo studies, lipid-based formulations containing dioctanoylglycol are typically administered to rodents via intravenous injection. Pharmacokinetic studies involve collecting blood samples at various time points and measuring drug or lipid concentrations by HPLC or LC-MS/MS. Biodistribution studies involve harvesting organs and measuring drug or lipid content. All animal procedures are conducted in accordance with institutional guidelines.
ADME/Pharmacokinetics
The pharmacokinetic properties of dioctanoylglycol as a lipid component are typically characterized in the context of the formulation. When administered, the lipid components are metabolized by esterases to release octanoic acid and ethylene glycol. The half-life of the lipid components in circulation depends on the formulation and surface modifications.
Toxicity/Toxicokinetics
The toxicology of dioctanoylglycol is primarily evaluated in the context of lipid-based formulations. As a lipid excipient, it is generally considered biocompatible and has low toxicity. In acute toxicity studies, the compound is well-tolerated at doses used for drug delivery. The compound is not genotoxic or carcinogenic. It is for research use only and is not approved for human therapeutic use.
References

[1]. Attenuation of sn-1,2-diacylglycerol second messengers by diacylglycerol kinase. Inhibition by diacylglycerol analogs in vitro and in human platelets. J Biol Chem. 1986 May 25;261(15):6993-7000.

Additional Infomation
Dioctanoylglycol is a glycolipid compound used as a component in lipid-based drug delivery systems. It is a diester of ethylene glycol and octanoic acid. The compound is not approved for human use and is intended for research purposes only. It is available as a high-purity research reagent for laboratory use.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C18H34O4
Molecular Weight
314.46016
Exact Mass
314.246
CAS #
627-86-1
Related CAS #
54406-23-4
PubChem CID
3093
Appearance
Colorless to light yellow liquid
Density
0.945g/cm3
Boiling Point
387.1ºC at 760 mmHg
Flash Point
179.8ºC
Index of Refraction
1.447
LogP
4.793
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
17
Heavy Atom Count
22
Complexity
248
Defined Atom Stereocenter Count
0
SMILES
CCCCCCCC(=O)OCCOC(=O)CCCCCCC
InChi Key
HTNFLUQQANUSLR-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H34O4/c1-3-5-7-9-11-13-17(19)21-15-16-22-18(20)14-12-10-8-6-4-2/h3-16H2,1-2H3
Chemical Name
2-octanoyloxyethyl octanoate
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

Note: This product requires protection from light (avoid light exposure) during transportation and storage.
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 (~318.01 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.95 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 (7.95 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
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 (7.95 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 3.1801 mL 15.9003 mL 31.8005 mL
5 mM 0.6360 mL 3.1801 mL 6.3601 mL
10 mM 0.3180 mL 1.5900 mL 3.1801 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.

Calculator

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An example of molarity calculation using the molarity calculator is shown below:
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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  • Enter 5 in the Volume box and choose the correct unit (mL)
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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  • The answer appears in the Volume (to add to vial) box
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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