| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Trilinolein has been reported to target multiple signaling pathways, including PI3K/Akt, MEK/ERK, and MMP pathways, and exhibits antioxidant activity. It reduces the production of oxygen-derived free radicals in leukocytes by preserving mitochondrial ultrastructure through antioxidant activity. The compound also reduces thrombogenicity and arrhythmias, and enhances erythrocyte deformability, suggesting interactions with platelet function and cardiovascular signaling systems. As a triglyceride, it is hydrolyzed by lipases to release free linoleic acid and glycerol.
|
|---|---|
| ln Vitro |
In vitro, trilinolein has been shown to reduce the production of oxygen-derived free radicals in leukocytes as measured by chemiluminescence assays. It preserves mitochondrial ultrastructure in isolated rat hearts subjected to global ischemia through its antioxidant activity. Trilinolein also inhibits the proliferation of cancer cells in some studies. Linoleic acid released from trilinolein by lipase action has additional biological activities, including anti-inflammatory and anti-atherogenic effects. Trilinolein serves as a substrate for various lipases in cell-free systems and is used as a standard in lipid analysis.
|
| ln Vivo |
In vivo, trilinolein has been reported to provide a number of beneficial effects in animal models, including reduced thrombogenicity (reduced blood clotting tendency) and reduced incidence of arrhythmias (irregular heartbeats), as well as increased erythrocyte (red blood cell) deformability, which improves blood flow through microcirculation. These effects have been attributed to the antioxidant properties of trilinolein, which preserves mitochondrial function and reduces oxidative stress in the cardiovascular system. Trilinolein has also been studied in isolated rat heart models of global ischemia, where it protects cardiac function.
|
| Enzyme Assay |
For non-cellular assays (enzyme activity), lipase activity can be measured using trilinolein as a substrate. The reaction mixture (1 mL) contains 50 mM Tris-HCl (pH 8.0), 5 mM CaCl2, 5 mM sodium taurodeoxycholate, 1 mg/mL trilinolein (emulsified with gum arabic), and lipase (10-100 ug). Incubate at 37degC for 30 minutes, and free fatty acids (linoleic acid) are quantified by titration with NaOH or by enzymatic assay. For antioxidant assays, chemiluminescence generated by xanthine/xanthine oxidase or by leukocytes can be measured using a luminometer in the presence or absence of trilinolein. For LC-MS analysis, trilinolein is dissolved in chloroform:methanol (2:1, v/v) and analyzed by LC-MS in positive ion mode (ammonium adduct [M+NH4]+ at m/z 898.7).
|
| Cell Assay |
For cell-based assays, leukocytes (neutrophils) isolated from human or animal blood are suspended in HBSS (1×10⁶ cells/mL) and treated with trilinolein (1-100 uM, pre-dissolved in ethanol or DMSO with sonication) for 30-60 minutes. Chemiluminescence is measured after addition of luminol (100 uM) and stimulation with phorbol myristate acetate (PMA, 1 ug/mL) using a luminometer. For mitochondrial studies, cardiac cells (e.g., H9c2 cardiomyoblasts) or isolated mitochondria are treated with trilinolein (1-50 uM) for 1-24 hours, and mitochondrial membrane potential (deltaΨm) is assessed using JC-1 or TMRM staining. ROS production is measured using MitoSOX Red or DCFH-DA.
|
| Animal Protocol |
For in vivo animal experiments, rat models of cardiac ischemia-reperfusion are used. Male Sprague-Dawley rats (8-12 weeks old) are anesthetized, and the heart is subjected to global ischemia (e.g., 30 minutes) followed by reperfusion (e.g., 60 minutes) on a Langendorff apparatus. Trilinolein (1-10 uM) is added to the perfusate before ischemia or during reperfusion. Cardiac function parameters (left ventricular developed pressure, heart rate, coronary flow) are measured. At the end of the experiment, heart tissues are collected for histological analysis (mitochondrial ultrastructure by electron microscopy) and biochemical assays (MDA levels, SOD activity, ATP content). For thrombosis studies, animals are administered trilinolein (10-50 mg/kg, oral or IP) prior to ferric chloride-induced arterial thrombosis.
|
| ADME/Pharmacokinetics |
Trilinolein has a molecular weight of 879.38, a density of 0.925 g/mL, and a logP of 17.425, indicating extremely high lipophilicity. It is insoluble in water but soluble in organic solvents such as DMSO (262.5 mg/mL), ethanol, and chloroform. The compound is a triglyceride with three linoleoyl (C18:2) fatty acid chains, making it highly susceptible to oxidation at the double bonds. It should be stored under nitrogen at -20degC to prevent auto-oxidation, and stored in sealed, dark containers. In solution, stability is limited (months at -80degC). The compound is liquid at room temperature.
|
| Toxicity/Toxicokinetics |
Toxicity Summary
It is safe at the current usage and concentration. Ingredient, concentration, and usage information can be found at: https://cir-reports.cir-safety.org Trilinolein has low acute toxicity. As an endogenous dietary triglyceride found in many vegetable oils and animal fats, it is generally recognized as safe (GRAS) when consumed as part of the diet. In animal studies, trilinolein is well-tolerated at doses up to 100 mg/kg. The release of polyunsaturated fatty acids (linoleic acid) by lipase action may have pro-inflammatory effects at high doses, but these are not observed at typical research doses. Standard laboratory safety precautions for handling lipids should be followed, including avoiding inhalation of aerosols and contact with skin. |
| Additional Infomation |
1,2,3-Trilinoleoylglycerol is a triglyceride formed by the acylation of the three hydroxyl groups of glycerol with linoleic acid. It is a mouse metabolite. It is a triglyceride belonging to the TG (18:2/18:2/18:2) class and contains linoleyl groups, including 1,2,3-triacyl-sn-glycerol, 1,2-diacyl-3-linoleoylglycerol, and 1,3-diacyl-2-linoleoylglycerol. It is functionally related to linoleic acid. Trilinoleic acid glycerides have been reported in ginseng, morel mushrooms, and several other organisms with relevant data. See also: Job's tears (partial).
Trilinolein is a research compound and endogenous metabolite, not an approved drug. No clinical trials have been conducted for therapeutic use. Its primary applications are in lipid metabolism research, nutritional biochemistry, and analytical chemistry as a reference standard. Trilinolein has been reported to provide beneficial cardiovascular effects including reduced thrombogenicity and arrhythmias and increased erythrocyte deformability in preclinical studies. It is also used as a substrate for lipase activity assays and in studies of lipid peroxidation and antioxidant defense. Trilinolein is available for research use only. |
| Molecular Formula |
C57H98O6
|
|---|---|
| Molecular Weight |
879.38
|
| Exact Mass |
878.736
|
| CAS # |
537-40-6
|
| PubChem CID |
5322095
|
| Appearance |
Colorless to light yellow liquid
|
| Density |
0.925 g/mL at 20 °C(lit.)
|
| Boiling Point |
816.5ºC at 760mmHg
|
| Flash Point |
302.9ºC
|
| Index of Refraction |
n20/D 1.479
|
| LogP |
17.425
|
| Hydrogen Bond Donor Count |
0
|
| Hydrogen Bond Acceptor Count |
6
|
| Rotatable Bond Count |
50
|
| Heavy Atom Count |
63
|
| Complexity |
1130
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O(C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)C([H])(C([H])([H])OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O)C([H])([H])OC(C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C(/[H])=C(/[H])\C([H])([H])/C(/[H])=C(/[H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
|
| InChi Key |
HBOQXIRUPVQLKX-BBWANDEASA-N
|
| InChi Code |
InChI=1S/C57H98O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-55(58)61-52-54(63-57(60)51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)53-62-56(59)50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h16-21,25-30,54H,4-15,22-24,31-53H2,1-3H3/b19-16-,20-17-,21-18-,28-25-,29-26-,30-27-
|
| Chemical Name |
2,3-bis[[(9Z,12Z)-octadeca-9,12-dienoyl]oxy]propyl (9Z,12Z)-octadeca-9,12-dienoate
|
| 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: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (113.72 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (2.84 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 (2.84 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), suspension 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. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.1372 mL | 5.6858 mL | 11.3716 mL | |
| 5 mM | 0.2274 mL | 1.1372 mL | 2.2743 mL | |
| 10 mM | 0.1137 mL | 0.5686 mL | 1.1372 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
