| Size | Price | Stock | Qty |
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| 5mg |
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| 10mg |
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| 50mg |
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| Targets |
1,2-Dilinoleoyl-sn-glycerol is a physiological activator of several isoforms of Protein Kinase C (PKC). It binds to the C1 domain of conventional (alpha, beta, gamma) and novel (delta, ε, η, θ) PKCs. As a DAG, it is a critical second messenger in the phosphoinositide signaling pathway. Upon binding, it translocates PKC from the cytosol to the membrane and activates it by increasing its affinity for Ca2+ and phosphatidylserine. This leads to the phosphorylation of downstream effectors involved in cell growth, differentiation, and metabolism.
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| ln Vitro |
In vitro, 1,2-Dilinoleoyl-sn-glycerol is a potent activator of purified PKC isoforms. In a cell-free PKC activity assay, 1 uM of this lipid typically induces maximal activation of the enzyme, with an EC₅0 in the range of 0.1-0.5 uM. It is often used as a positive control in PKC activity assays. It has no significant cytotoxicity at these concentrations. It can also directly activate RasGRP, a guanine nucleotide exchange factor involved in MAPK signaling, although its primary target is PKC.
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| ln Vivo |
In vivo, 1,2-Dilinoleoyl-sn-glycerol is not administered exogenously. It functions as an endogenous signaling molecule. It has been identified as a potential biomarker; it is upregulated in some pregnant women and has been used to predict later preeclampsia in early pregnancy. However, there are no reports of exogenous administration in animal models for therapeutic purposes, as it is rapidly metabolized by diacylglycerol kinases and lipases. Its in vivo efficacy is limited to its role as an intracellular second messenger.
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| Enzyme Assay |
For PKC activation assays, a cell-free system is used. The lipid is incorporated into lipid vesicles (micelles) to present it to the enzyme. The following are mixed: 20 mol% 1,2-Dilinoleoyl-sn-glycerol, 20 mol% phosphatidylserine, and 60 mol% phosphatidylcholine in chloroform. The solvent is evaporated, and the lipid film is hydrated in 20 mM HEPES (pH 7.4). Purified PKC (5 ng) is incubated with the lipid vesicles, 0.5 mM CaCl2, and the PKC substrate peptide (e.g., Ac-FKKSFKL-NH2) in 20 mM HEPES (pH 7.4) containing 10 mM MgCl2 for 10 min. Phosphorylation is measured using a luminescent kinase assay.
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| Cell Assay |
No standard cell-based therapeutic assays are performed for 1,2-Dilinoleoyl-sn-glycerol because it is a labile second messenger. It is used to study DAG-mediated signaling. Cells (e.g., HeLa or NIH3T3) are serum-starved, then treated with the DAG (1-50 uM) in the presence of a DAG kinase inhibitor (e.g., R59022) to prevent metabolism. PKC activation is detected by the translocation of GFP-tagged PKCgamma from the cytosol to the plasma membrane using confocal microscopy. Phosphorylation of PKC substrates (e.g., MARCKS) is measured by Western blot.
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| Animal Protocol |
No animal experiments have been conducted with this compound as a test article for efficacy. It is an endogenous lipid and is not used as a drug. Researchers may use animal models to study preeclampsia, where serum levels of this DAG are measured as a biomarker. However, the lipid itself is not administered. For biosynthetic studies, 14C-labeled linoleic acid is injected into rats, and the incorporation into 1,2-dilinoleoyl-sn-glycerol in liver mitochondria is measured. The compound serves as an analytical endpoint, not a treatment.
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| ADME/Pharmacokinetics |
The pharmacokinetics of 1,2-Dilinoleoyl-sn-glycerol as a pure compound are not defined because it is an endogenous intermediate. Any exogenous DAG is rapidly phosphorylated by diacylglycerol kinases (DGKs) to produce phosphatidic acid (PA) or hydrolyzed by lipases. The half-life in plasma is less than one minute. It is highly lipophilic and binds to lipoproteins. It is not a drug candidate, so no formal PK studies exist. It is simply a reference standard for analyzing these metabolic pathways.
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| Toxicity/Toxicokinetics |
Toxicity studies for 1,2-Dilinoleoyl-sn-glycerol are not required, as it is an endogenous lipid and not a drug. No acute LD₅0 data are available. It is considered non-toxic. In cell culture, it is well-tolerated at concentrations up to 50 uM. There is no evidence of skin irritation, mutagenicity, or reproductive toxicity. Standard laboratory safety practices are sufficient. The compound is typically stored at -20degC in organic solvents (e.g., chloroform).
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| References | |
| Additional Infomation |
1,2-Dilinoleoyl-sn-glycerol is a 1,2-diacyl-sn-glycerol in which both acyl groups are linoleyl groups. It is a mouse metabolite. It is both dilinoleoylglycerol and 1,2-diacyl-sn-glycerol. It is functionally related to linoleic acid. It is the enantiomer of 2,3-dilinoleoyl-sn-glycerol. 1,2-Dilinoleoyl-sn-glycerol has been reported and data are available in Sciadopitys verticillata.
1,2-Dilinoleoyl-sn-glycerol is not a drug and has no regulatory approvals (FDA, EMA). It is a high-purity (≥99%) lipid standard for research. Its primary application is as a standard in lipidomics (LC-MS/MS) to quantify DAG species in biological samples. It is also used as a positive control in protein kinase C (PKC) assays. Additionally, it serves as a reference material for studies on diacylglycerol metabolism and signaling. Synonyms include 1,2-di(9Z,12Z-octadecadienoyl)-sn-glycerol. It is stored at -20degC. |
| Molecular Formula |
C39H68O5
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| Molecular Weight |
616.95
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| Exact Mass |
616.507
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| CAS # |
24529-89-3
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| PubChem CID |
9543729
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| Appearance |
Colorless to light yellow liquid
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| LogP |
11.061
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
34
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| Heavy Atom Count |
44
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| Complexity |
752
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| Defined Atom Stereocenter Count |
1
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| SMILES |
CCCCCC=CCC=CCCCCCCCC(=O)OCC(CO)OC(=O)CCCCCCCC=CCC=CCCCCC
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| InChi Key |
MQGBAQLIFKSMEM-ZHARMHCNSA-N
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| InChi Code |
InChI=1S/C39H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h11-14,17-20,37,40H,3-10,15-16,21-36H2,1-2H3/b13-11-,14-12-,19-17-,20-18-/t37-/m0/s1
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| Chemical Name |
[(2S)-3-hydroxy-2-[(9Z,12Z)-octadeca-9,12-dienoyl]oxypropyl] (9Z,12Z)-octadeca-9,12-dienoate
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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 | 1.6209 mL | 8.1044 mL | 16.2088 mL | |
| 5 mM | 0.3242 mL | 1.6209 mL | 3.2418 mL | |
| 10 mM | 0.1621 mL | 0.8104 mL | 1.6209 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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