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Trilaurin

Alias: NSC 4061; Glyceryl tridodecanoate; Trilaurin
Cat No.:V16811 Purity: ≥98%
Trilaurin inhibits the formation of tumors caused by dimethylbenzanthracene (DMBA) promoted by croton oil.
Trilaurin
Trilaurin Chemical Structure CAS No.: 538-24-9
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1g
Other Sizes

Other Forms of Trilaurin:

  • Trilaurin-d15
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Trilaurin inhibits the formation of tumors caused by dimethylbenzanthracene (DMBA) promoted by croton oil.
Trilaurin, also known as glyceryl tridodecanoate, is a homogeneous, saturated triacylglycerol (TAG) consisting of a glycerol backbone esterified with three molecules of lauric acid (C12:0). It is a medium-chain triglyceride (MCT) found in dietary fats and is used in cosmetic products as a thickening agent, emulsifier, and emollient. Trilaurin is a white, waxy solid at room temperature with a melting point range of 44-49°C. It is also employed in research as an antigenotoxic positive control and a model compound for studying lipid hydrolysis and transesterification reactions.
Biological Activity I Assay Protocols (From Reference)
Targets
Trilaurin does not have a specific molecular target in the context of drug action; rather, it functions as a nutritional lipid and a metabolic substrate. As a triglyceride, it is hydrolyzed by lipases to release lauric acid, which can be utilized as an energy source or incorporated into cellular lipids. Lauric acid is a medium-chain fatty acid with unique metabolic properties, as it is absorbed and metabolized differently from long-chain fatty acids. In research, trilaurin is used as a model compound to study lipid metabolism, digestion, and absorption. It has also been studied for its potential to inhibit the formation of neoplasms.
ln Vitro
In vitro, trilaurin is used as a substrate in studies of lipid metabolism and digestion. It is hydrolyzed by pancreatic lipase and other esterases to release lauric acid and glycerol. Cell-based assays can be used to study the uptake and metabolism of trilaurin or its hydrolysis products. For example, cultured adipocytes or hepatocytes can be treated with trilaurin or lauric acid, and the effects on lipid accumulation, gene expression, and cellular signaling can be measured. It has also been shown to inhibit the formation of neoplasms initiated by dimethylbenzanthracene (DMBA) and promoted by croton oil in vitro.
ln Vivo
In vivo, trilaurin is used as a dietary lipid and has been studied for its biological effects. In animal models, it has been shown to inhibit the formation of skin tumors initiated by DMBA and promoted by croton oil. This suggests potential chemopreventive properties. As a source of lauric acid, trilaurin may influence lipid metabolism, immune function, and other physiological processes. It is also used as a component of research diets to study the effects of medium-chain triglycerides on metabolism and health.
Enzyme Assay
In vitro enzyme or receptor binding (non-cell) assays for trilaurin are not typically performed, as it is not a direct enzyme inhibitor or receptor ligand. However, its hydrolysis by lipases can be studied using in vitro enzymatic assays. For example, pancreatic lipase can be incubated with trilaurin in the presence of bile salts, and the release of fatty acids can be measured by titration or using a pH-stat method. The activity of other lipases, such as hepatic lipase or lipoprotein lipase, can also be assessed using trilaurin as a substrate. These assays are used to characterize the enzymatic hydrolysis of triglycerides.
Cell Assay
In vitro cell-based assays for trilaurin are performed using various cell lines to study its effects on cellular metabolism and function. Adipocytes, hepatocytes, or intestinal epithelial cells can be treated with trilaurin or its hydrolysis products. The uptake and metabolism of lauric acid can be traced using radiolabeled or fluorescently labeled compounds. The effects on lipid accumulation, gene expression, and inflammatory responses are measured. Cell viability and proliferation assays can also be performed to assess any potential cytotoxic or proliferative effects.
Animal Protocol
In vivo animal experiments for trilaurin are conducted using rodent models to study its metabolic effects and potential health benefits. Animals are fed a diet containing trilaurin or a control diet, and various parameters are measured, including body weight, food intake, serum lipid levels, and tissue lipid content. In carcinogenesis studies, animals are treated with a carcinogen (e.g., DMBA) and then fed a diet containing trilaurin, and the incidence and multiplicity of tumors are assessed. These studies help to understand the role of dietary lipids in health and disease.
ADME/Pharmacokinetics
Pharmacokinetic (PK) properties of trilaurin are typical of a medium-chain triglyceride. After oral administration, it is hydrolyzed in the gastrointestinal tract by lipases to release lauric acid and glycerol. Lauric acid is absorbed and transported via the portal vein to the liver, where it is rapidly metabolized. The compound has a molecular weight of 639.0 g/mol and a molecular formula of C39H74O6. It is soluble in DMSO and other organic solvents. The powder should be stored in a dry, dark place at 0-4°C for short-term storage or at -20°C for long-term storage.
Toxicity/Toxicokinetics
Toxicology (toxicology) data for trilaurin indicate that it is generally recognized as safe (GRAS) for use in food and cosmetics. As a naturally occurring triglyceride, it has a low inherent toxicity. Oral administration of trilaurin is well-tolerated, and no significant adverse effects have been reported at typical dietary levels. In high doses, it may cause gastrointestinal discomfort, such as diarrhea, which is common with the consumption of large amounts of medium-chain triglycerides. It is not considered genotoxic, carcinogenic, or teratogenic.
References

[1]. Final report on the safety assessment of trilaurin, triarachidin, tribehenin, tricaprin, tricaprylin, trierucin, triheptanoin, triheptylundecanoin, triisononanoin, triisopalmitin, triisostearin, trilinolein, trimyristin, trioctanoin, triolein, tripalmitin, tripalmitolein, triricinolein, tristearin, triundecanoin, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, and glyceryl stearate diacetate. Int J Toxicol. 2001;20 Suppl 4:61-94.

Additional Infomation
Trilauric acid glyceride is a triglyceride obtained by acylation of the three hydroxyl groups of glycerol with lauric acid (ladecanoic acid). It is both a triglyceride and a lauryl ester. Trilauric acid glyceride has been reported in both Cullen corylifolium and Umbellularia californica, and relevant data are available for reference.
Other information: Trilaurin is a naturally occurring triglyceride found in coconut oil, palm kernel oil, and other dietary fats. It is used in the food, cosmetic, and pharmaceutical industries as an emulsifier, stabilizer, thickening agent, and emollient. In research, it is used as a model compound for studying lipid metabolism and as an antigenotoxic positive control. Its CAS number is 538-24-9.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C39H74O6
Molecular Weight
639.015
Exact Mass
638.548
CAS #
538-24-9
Related CAS #
Trilaurin-d15;1219805-25-0
PubChem CID
10851
Appearance
White to off-white solid powder
Density
0.9±0.1 g/cm3
Boiling Point
643.3±22.0 °C at 760 mmHg
Melting Point
46.5 °C(lit.)
Flash Point
253.5±22.4 °C
Vapour Pressure
0.0±1.9 mmHg at 25°C
Index of Refraction
1.463
LogP
15.7
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
38
Heavy Atom Count
45
Complexity
626
Defined Atom Stereocenter Count
0
InChi Key
VMPHSYLJUKZBJJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C39H74O6/c1-4-7-10-13-16-19-22-25-28-31-37(40)43-34-36(45-39(42)33-30-27-24-21-18-15-12-9-6-3)35-44-38(41)32-29-26-23-20-17-14-11-8-5-2/h36H,4-35H2,1-3H3
Chemical Name
2,3-di(dodecanoyloxy)propyl dodecanoate
Synonyms
NSC 4061; Glyceryl tridodecanoate; Trilaurin
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 : ~4 mg/mL (~6.26 mM)
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.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.5649 mL 7.8245 mL 15.6490 mL
5 mM 0.3130 mL 1.5649 mL 3.1298 mL
10 mM 0.1565 mL 0.7824 mL 1.5649 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

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
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.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • 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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