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1-Oleoyl-2-acetyl-sn glycerol

Cat No.:V50967 Purity: ≥98%
1-Oleoyl-2-acetyl-sn glycerol is a synthetic, cell-penetrating/penetrable diacylglycerol analog.
1-Oleoyl-2-acetyl-sn glycerol
1-Oleoyl-2-acetyl-sn glycerol Chemical Structure CAS No.: 86390-77-4
Product category: PKC
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
500mg
1g
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Product Description
1-Oleoyl-2-acetyl-sn glycerol is a synthetic, cell-penetrating/penetrable diacylglycerol analog. 1-Oleoyl-2-acetyl-sn glycerol activates calcium-dependent protein kinase C (PKC) and induces superoxide production.
1-Oleoyl-2-acetyl-sn-glycerol (OAG) is a synthetic, cell-permeable analog of the endogenous second messenger diacylglycerol (DAG). It is often used as an activator of calcium-dependent protein kinase C (PKC). OAG has a molecular weight of 398.58 g/mol and a chemical formula of C23H42O5.
Biological Activity I Assay Protocols (From Reference)
Targets
1-Oleoyl-2-acetyl-sn-glycerol targets protein kinase C (PKC), a family of serine/threonine kinases that play a critical role in cell signaling. PKC is activated by DAG and calcium. As a cell-permeable DAG analog, OAG binds to the C1 domain of PKC and activates it, mimicking the effects of endogenous DAG. This activation leads to the phosphorylation of downstream targets and the regulation of various cellular processes.
ln Vitro
In vitro, 1-Oleoyl-2-acetyl-sn-glycerol is a potent activator of calcium-dependent PKC. It induces the superoxide-production. Its activity is typically assessed by measuring PKC activity in cell lysates or by using purified PKC in kinase assays. Its cell-permeable nature allows it to be used in intact cells to study PKC-mediated signaling.
ln Vivo
In vivo, 1-Oleoyl-2-acetyl-sn-glycerol is used to study the role of PKC in various physiological and pathological processes. Its ability to activate PKC makes it a valuable tool for investigating the downstream effects of PKC signaling. Specific in vivo studies, including dosing and administration routes, are not detailed in the provided sources but would be described in the primary literature.
Enzyme Assay
The activity of 1-Oleoyl-2-acetyl-sn-glycerol is assessed using in vitro PKC activity assays. Purified PKC is incubated with a peptide substrate, ATP, and varying concentrations of OAG in the presence of calcium and phosphatidylserine. The transfer of phosphate to the substrate is measured, and the EC50 is calculated. Its cell-permeable nature is confirmed by its ability to activate PKC in intact cells.
Cell Assay
The cellular activity of 1-Oleoyl-2-acetyl-sn-glycerol is evaluated in various cell types. Cells are treated with OAG, and its effect on PKC activity is measured by assessing the phosphorylation of PKC substrates. Its effect on downstream signaling pathways, such as the MAPK pathway, is assessed by Western blot. Its effect on cell function, such as superoxide production, is also measured.
Animal Protocol
In animal studies, 1-Oleoyl-2-acetyl-sn-glycerol would typically be administered via injection to study the effects of PKC activation in vivo. Its effect on signaling pathways, physiological responses, and disease models would be assessed. However, specific in vivo protocols for OAG are not detailed in the provided sources.
ADME/Pharmacokinetics
1-Oleoyl-2-acetyl-sn-glycerol has a molecular weight of 398.58 g/mol and a chemical formula of C23H42O5. It is an oil (neat) with a purity of ≥95% (TLC). It is soluble in DMSO and ethanol and is typically stored at -20°C. Its stability and solubility are important for its use in cell-based assays.
Toxicity/Toxicokinetics
Formal toxicology data for 1-Oleoyl-2-acetyl-sn-glycerol is not extensively documented, as it is a research compound. Its use in cell-based assays at effective concentrations suggests it is tolerated in those contexts. Its use is limited to research applications.
References

[1]. Fujita I, Irita K, Takeshige K, Minakami S. Diacylglycerol, 1-oleoyl-2-acetyl-glycerol, stimulates superoxide-generation from human neutrophils. Biochem Biophys Res Commun. 1984;120(2):318-324.

[2]. Martin AC, Cooper DM. Capacitative and 1-oleyl-2-acetyl-sn-glycerol-activated Ca(2+) entry distinguished using adenylyl cyclase type 8. Mol Pharmacol. 2006;70(2):769-777.

Additional Infomation
1-Oleoyl-2-acetyl-sn-glycerol is a 1,2-diglyceride.
1-Oleoyl-2-acetyl-sn-glycerol (OAG, CAS: 86390-77-4) is a widely used research tool for studying PKC signaling. Its cell-permeable nature and its ability to activate calcium-dependent PKC make it a valuable tool for investigating the role of PKC in various cellular processes. It is available from various commercial suppliers for research purposes.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C23H42O5
Exact Mass
398.303
CAS #
86390-77-4
PubChem CID
6437055
Appearance
Colorless to light yellow liquid
Density
1.0±0.1 g/cm3
Boiling Point
490.0±15.0 °C at 760 mmHg
Flash Point
152.3±13.9 °C
Vapour Pressure
0.0±2.8 mmHg at 25°C
Index of Refraction
1.471
LogP
7.45
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
21
Heavy Atom Count
28
Complexity
406
Defined Atom Stereocenter Count
1
SMILES
[C@@H](CO)(OC(=O)C)COC(=O)CCCCCCC/C=C\CCCCCCCC
InChi Key
PWTCCMJTPHCGMS-YRBAHSOBSA-N
InChi Code
InChI=1S/C23H42O5/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-23(26)27-20-22(19-24)28-21(2)25/h10-11,22,24H,3-9,12-20H2,1-2H3/b11-10-/t22-/m0/s1
Chemical Name
[(2S)-2-acetyloxy-3-hydroxypropyl] (Z)-octadec-9-enoate
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)
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
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
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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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