 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C9H6O6 |
| Molecular Weight | 210.14 |
| Exact Mass | 210.016 |
| CAS # | 554-95-0 |
| Related CAS # | Benzene-1,3,5-tricarboxylic acid-d3;62790-27-6 |
| PubChem CID | 11138 |
| Appearance | White to off-white solid powder |
| Density | 1.7±0.1 g/cm3 |
| Boiling Point | 561.4±45.0 °C at 760 mmHg |
| Melting Point | >300 °C(lit.) |
| Flash Point | 307.4±25.2 °C |
| Vapour Pressure | 0.0±1.6 mmHg at 25°C |
| Index of Refraction | 1.663 |
| LogP | 1.51 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 3 |
| Heavy Atom Count | 15 |
| Complexity | 237 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O([H])C(C1C([H])=C(C(=O)O[H])C([H])=C(C(=O)O[H])C=1[H])=O |
| InChi Key | QMKYBPDZANOJGF-UHFFFAOYSA-N |
| 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) |
| Chemical Name | benzene-1,3,5-tricarboxylic acid |
| Synonyms | Trimesic acid; NSC 3998; TMA; NSC-3998; benzene-1,3,5-tricarboxylic acid; 1,3,5-BENZENETRICARBOXYLIC ACID; Trimesinic acid; Trimesitinic acid; 5-Carboxyisophthalic acid; 1,3,5-Tricarboxybenzene; |
| 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) |
Biological Activity
| Targets | Biochemical reagent |
| ln Vitro |
1,3,5-Benzenetricarboxylic acid/trimesic acid is a natural product that has been reported in Phaseolus vulgaris. Citric acid and trimesic acid reversibly reduced the activity of YopH enzyme and decreased the viability of Jurkat and macrophage cell lines. Importantly, these two compounds showed greater inhibitory properties against bacterial YopH activity than against human CD45 phosphatase activity. Molecular docking simulations confirmed that citric acid could bind to YopH phosphatase. Conclusion: Citric acid, a known antioxidant, can be considered an inhibitor of bacterial phosphatases.[2] Protein-protein interactions represent a new class of exciting but challenging drug targets, because their large, flat binding sites lack well-defined pockets for small molecules to bind. We report here a methodology for chemical synthesis and screening of large combinatorial libraries of bicyclic peptides displayed on rigid small-molecule scaffolds. With planar 1,3,5-Benzenetricarboxylic acid/trimesic acid as the scaffold, the resulting bicyclic peptides are effective for binding to protein surfaces such as the interfaces of protein-protein interactions. Screening of a bicyclic peptide library against tumor necrosis factor-α (TNFα) identified a potent antagonist that inhibits the TNFα-TNFα receptor interaction and protects cells from TNFα-induced cell death. Bicyclic peptides of this type may provide a general solution for inhibition of protein-protein interactions.[1] |
| Enzyme Assay | In this study, researchers performed enzymatic activity assays of YopH phosphatase after treatment with citric acid in comparison with the inhibitory compound 1,3,5-Benzenetricarboxylic acid/trimesic acid, which has a similar structure. They also measured the cytotoxicity of these compounds in Jurkat T E6.1 and macrophage J774.2 cell lines. Researchers performed molecular docking analysis of the binding of citric acid molecules to YopH phosphatase.[2] |
| References |
[1]. Screening bicyclic peptide libraries for protein-protein interaction inhibitors: Discovery of a tumor necrosis factor-α antagonist. J Am Chem Soc. 2013 Aug 14;135(32):11990-5. [2]. Citric Acid Controls the Activity of YopH Bacterial Tyrosine Phosphatase. Drug Des Devel Ther. 2024 Apr 11:18:1165-1174. |
| Additional Infomation |
Benzene-1,3,5-tricarboxylic acid is a tricarboxylic acid that consists of benzene substituted by carboxy groups at positions 1, 3 and 5. It is a tricarboxylic acid and a member of benzoic acids. It is a conjugate acid of a benzene-1,3,5-tricarboxylate(1-). 1,3,5-Benzenetricarboxylic acid has been reported in Phaseolus vulgaris with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO: 100 mg/mL (475.87 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (11.90 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 (11.90 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), 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 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. Solubility in Formulation 3: ≥ 2.5 mg/mL (11.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (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 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.7587 mL | 23.7937 mL | 47.5873 mL | |
| 5 mM | 0.9517 mL | 4.7587 mL | 9.5175 mL | |
| 10 mM | 0.4759 mL | 2.3794 mL | 4.7587 mL |