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| 5mg |
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| 10mg |
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Benzene-1,3,5-tricarboxylic acid-d3 is a stable isotope-labeled internal standard for its parent compound. The unlabeled compound, Trimesic acid (Benzene-1,3,5-tricarboxylic acid), is not a drug with a biological target; rather, it is an organic building block. Its primary applications are in materials science, where it acts as a multidentate ligand. It coordinates with metal ions (e.g., Cu2+, Zn2+, Al3+) to form highly porous metal-organic frameworks (MOFs). These frameworks have high surface areas and are used for gas storage (hydrogen, methane, carbon dioxide), gas separation, and catalysis. In biological research, trimesic acid has been studied as a potential inhibitor of enzymes such as carbonic anhydrase, though this is not its primary use. The deuterated version is used to accurately quantify the leaching or release of the linker from MOFs in biological media.
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| ln Vitro |
Drug compounds have included stable heavy isotopes of carbon, hydrogen, and other elements, mostly as quantitative tracers while the drugs were being developed. Because deuteration may have an effect on a drug's pharmacokinetics and metabolic properties, it is a cause for concern [1].
Benzene-1,3,5-tricarboxylic acid-d3 is not a pharmacologically active compound and has no intrinsic biological activity. Its unlabeled counterpart, trimesic acid, is generally considered biologically inert and has low toxicity. However, in vitro studies have investigated its potential as a building block for drug delivery systems. For instance, when incorporated into nanoscale metal-organic frameworks (nano-MOFs), trimesic acid does not exhibit significant cytotoxic effects on mammalian cell lines (e.g., HeLa, HEK293) at concentrations below 100 uM. In some studies, it has been used as a non-toxic linker to encapsulate anticancer drugs. In enzymatic assays, trimesic acid has been shown to weakly inhibit the activity of certain metalloproteases and carbonic anhydrases at high millimolar concentrations due to its ability to chelate the zinc ion in the active site. The labeled version (d3) is used as an internal standard for LC-MS analysis to measure the concentration of trimesic acid released from these materials in cell culture media. |
| ln Vivo |
Benzene-1,3,5-tricarboxylic acid-d3 is not a pharmacologically active substance and is used only as an analytical standard. The unlabeled trimesic acid is considered to have low in vivo toxicity and is not typically administered to animals for therapeutic purposes. However, in animal studies of material safety, trimesic acid (administered via intravenous or intraperitoneal injection at 10-50 mg/kg) has been used to evaluate the biocompatibility of metal-organic frameworks. In these studies, it is generally well-tolerated without causing significant changes in body weight, organ histology, or serum biomarkers of liver and kidney function (ALT, AST, creatinine). It is rapidly cleared from the bloodstream, primarily through renal excretion. The labeled Benzene-1,3,5-tricarboxylic acid-d3 serves as an internal standard in LC-MS assays to accurately quantify the concentration of trimesic acid in plasma, urine, and tissue homogenates for toxicokinetic assessment.
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| Enzyme Assay |
As Benzene-1,3,5-tricarboxylic acid-d3 is an analytical standard, a generic non-cell-based assay involves its use as an internal standard in an LC-MS method for quantifying trimesic acid in a matrix. First, prepare a standard stock solution of the unlabeled trimesic acid in water or methanol at 1 mg/mL. Prepare a separate stock solution of the internal standard (Benzene-1,3,5-tricarboxylic acid-d3) at the same concentration. Prepare calibration standards by serially diluting the unlabeled analyte in a blank matrix (e.g., PBS buffer or cell culture media) to achieve concentrations ranging from 10 ng/mL to 10 ug/mL. To each calibration standard, add a fixed concentration of the internal standard (e.g., 500 ng/mL). Also prepare blank and double-blank samples. For sample preparation, mix 100 uL of the calibration standard with 300 uL of methanol to precipitate proteins. Centrifuge at 12,000g for 5 minutes. Transfer the supernatant to an autosampler vial. Analyze the samples by LC-MS/MS in negative ion mode, monitoring the specific mass transitions for the analyte (m/z 210 → 166) and the internal standard (m/z 213 → 169). Construct the calibration curve by plotting the peak area ratio (analyte/IS) vs. the nominal concentration.
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| Cell Assay |
There are no standard cell-based assays for Benzene-1,3,5-tricarboxylic acid-d3, as it is not a bioactive compound. However, if one wanted to test the cytotoxicity of its unlabeled counterpart, a standard MTT protocol can be used. Culture a common cell line such as HEK293 (human embryonic kidney) or HepG2 (hepatocellular carcinoma) in DMEM with 10% FBS and 1% penicillin/streptomycin at 37degC in a 5% CO2 incubator. Seed the cells at 8,000 cells per well in 96-well plates and allow them to attach overnight. Treat the cells with increasing concentrations of unlabeled trimesic acid (10 uM, 50 uM, 100 uM, 500 uM) or vehicle (PBS) for 24-72 hours. After treatment, add 10 uL of MTT solution (5 mg/mL) to each well and incubate for 3 hours. Then, remove the medium and add 100 uL of DMSO to dissolve the formazan crystals. Measure the absorbance at 570 nm using a microplate reader. Calculate the percentage of cell viability relative to the vehicle control. Use Benzene-1,3,5-tricarboxylic acid-d3 as an internal standard to quantify the exact concentration of trimesic acid in the cell culture medium by LC-MS.
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| Animal Protocol |
A standard in vivo protocol for Benzene-1,3,5-tricarboxylic acid-d3 involves a toxicokinetic study in rats to assess the clearance of the compound. Use male Sprague-Dawley rats (200-250 g, n=3-5 per group). Administer a single intravenous (IV) dose of unlabeled trimesic acid (10 mg/kg) dissolved in saline. Collect blood samples (~200 uL) from the tail vein at various time points (0, 5, 15, 30 min, 1, 2, 4, 6, 8, 12, 24 h) into heparinized tubes. Immediately centrifuge the blood samples to obtain plasma. Also collect urine and feces over 24 hours if metabolic cages are available. For bioanalysis, spike an aliquot of plasma (50 uL) with a fixed concentration of Benzene-1,3,5-tricarboxylic acid-d3 as the internal standard. Precipitate proteins with acetonitrile, centrifuge, and inject the supernatant onto an LC-MS/MS system. Calculate the pharmacokinetic parameters including terminal half-life (t½), volume of distribution (Vd), and clearance (CL) using non-compartmental analysis.
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| ADME/Pharmacokinetics |
Benzene-1,3,5-tricarboxylic acid-d3 is not a drug; therefore, its pharmacokinetic properties are not typically studied. It is used as an internal standard. However, the ADME profile of its unlabeled counterpart, trimesic acid, is known from studies on metal-organic frameworks (MOFs). Trimesic acid is a small, hydrophilic molecule. It is poorly absorbed from the gastrointestinal tract due to its high polarity (log P approx. 1.2). Following intravenous administration, it exhibits a relatively short elimination half-life (approximately 30-60 minutes in rats) and is rapidly cleared from the plasma. The volume of distribution is low (approx. 0.2-0.3 L/kg), indicating it is confined primarily to the extracellular fluid. It is not extensively metabolized and is excreted unchanged in the urine. The labeled compound (d3) is used as an internal standard for LC-MS analysis to accurately measure these parameters.
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| Toxicity/Toxicokinetics |
Benzene-1,3,5-tricarboxylic acid-d3 (Trimesic acid-d3) is a stable isotope-labeled research compound and is not a pharmaceutical drug. The toxicity of its unlabeled parent compound, trimesic acid, is generally considered low. The oral LD₅0 for trimesic acid in rats is >5000 mg/kg, indicating very low acute toxicity. It is not classified as a carcinogen, mutagen, or reproductive toxin. However, like many organic acids, it may be a mild skin, eye, and respiratory tract irritant. Exposure to large amounts of dust may cause mechanical irritation. Standard laboratory safety precautions, such as the use of gloves, safety goggles, and a lab coat, are recommended when handling this compound. The compound should be stored in a tightly closed container in a cool, dry, well-ventilated area, away from incompatible substances. It is for research use only and not intended for human use.
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| References | |
| Additional Infomation |
Benzene-1,3,5-tricarboxylic acid-d3 (Trimesic acid-d3) is a stable isotope-labeled version of trimesic acid. It is used as an internal standard for the quantification of trimesic acid in analytical chemistry and material science research using LC-MS. The unlabeled trimesic acid is a planar, C3-symmetric aromatic carboxylic acid. It is a key organic building block or linker extensively used in the synthesis of metal-organic frameworks (MOFs), covalent organic frameworks (COFs), and coordination polymers for applications in gas storage, gas separation, heterogeneous catalysis, and drug delivery. Due to its low toxicity profile, it is also being explored as a safe component in biomedical materials. This deuterated compound allows researchers to precisely track the linker integrity and stability in these advanced materials under biological conditions.
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| Molecular Formula |
C9H3D3O6
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| Molecular Weight |
213.16
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| Exact Mass |
213.035
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| CAS # |
62790-27-6
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| Related CAS # |
Benzene-1,3,5-tricarboxylic acid;554-95-0
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| PubChem CID |
102602248
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| Appearance |
White to off-white solid powder
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| LogP |
0.781
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| Hydrogen Bond Donor Count |
3
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
15
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| Complexity |
237
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| Defined Atom Stereocenter Count |
0
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| SMILES |
[2H]C1=C(C(=C(C(=C1C(=O)O)[2H])C(=O)O)[2H])C(=O)O
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| InChi Key |
QMKYBPDZANOJGF-CBYSEHNBSA-N
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| InChi Code |
InChI=1S/C9H6O6/c10-7(11)4-1-5(8(12)13)3-6(2-4)9(14)15/h1-3H,(H,10,11)(H,12,13)(H,14,15)/i1D,2D,3D
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| Chemical Name |
2,4,6-trideuteriobenzene-1,3,5-tricarboxylic acid
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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) |
DMSO: 125 mg/mL (586.41 mM)
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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 | 4.6913 mL | 23.4566 mL | 46.9131 mL | |
| 5 mM | 0.9383 mL | 4.6913 mL | 9.3826 mL | |
| 10 mM | 0.4691 mL | 2.3457 mL | 4.6913 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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