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Physicochemical Properties
| Molecular Formula | C42H63O4P |
| Molecular Weight | 662.92099404335 |
| Exact Mass | 662.446 |
| Elemental Analysis | C, 76.10; H, 9.58; O, 9.65; P, 4.67 |
| CAS # | 95906-11-9 |
| PubChem CID | 14572930 |
| Appearance | White to off-white solid powder |
| Melting Point | 99-101 °C(lit.) |
| LogP | 13.116 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 12 |
| Heavy Atom Count | 47 |
| Complexity | 920 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | O=P(OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1)(OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1)OC1C(C(C)(C)C)=CC(C(C)(C)C)=CC=1 |
| InChi Key | AZSKHRTUXHLAHS-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C42H63O4P/c1-37(2,3)28-19-22-34(31(25-28)40(10,11)12)44-47(43,45-35-23-20-29(38(4,5)6)26-32(35)41(13,14)15)46-36-24-21-30(39(7,8)9)27-33(36)42(16,17)18/h19-27H,1-18H3 |
| Chemical Name | tris(2,4-ditert-butylphenyl) phosphate |
| Synonyms | AAN06119; AAN-06119; AAN 06119; tris(2,4-di-tert-butylphenyl)phosphate; Tris(2,4-ditert-butylphenyl)phosphate; tris(2,4-di-tert-butylphenyl) phosphate; Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphate (3:1); tris(2,4-ditert-butylphenyl) phosphate; Phenol, 2,4-bis(1,1-dimethylethyl)-, 1,1',1''-phosphate; F32IRS6B46; |
| 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 |
sPLA2/secretory Phospholipase A2 Target: Tris(2,4-di-tert-butylphenyl)phosphate targets secretory Phospholipase A₂ (sPLA₂), with molecular docking experiments showing specific binding to the active site of sPLA₂. [1] |
| ln Vitro |
Novel compounds with significant medicinal properties have gained much interest in therapeutic approaches for treating various inflammatory disorders like arthritis, odema and snake bites and the post-envenom (impregnating with venom) consequences. Inflammation is caused by the increased concentration of secretory Phospholipases A(2) (sPLA(2)s) at the site of envenom. A novel compound Tris(2,4-di-tert-butylphenyl) phosphate (TDTBPP) was isolated from the leaves of Vitex negundo and the crystal structure was reported recently[1]. sPLA₂ Binding and Inhibitory Activity: Molecular docking analysis confirmed that Tris(2,4-di-tert-butylphenyl)phosphate can stably bind to the catalytic active site of sPLA₂ with a binding energy of -7.8 kcal/mol, indicating high affinity. This binding blocks the catalytic function of sPLA₂, thereby inhibiting the production of inflammatory mediators and exerting anti-inflammatory effects [1] |
| ln Vivo | A carrageenan-induced foot edema model shows notable anti-inflammatory activity in response to 50 mg/kg and 70 mg/kg of tris(2,4-di-tert-butylphenyl)phosphate (TDTBPP) [1]. The volume of raw claw edema can be considerably decreased by using 50 mg/kg and 70 mg/kg of tris(2,4-di-tert-butylphenyl)phosphate [1]. |
| Enzyme Assay |
Molecular Docking Experiment of sPLA₂ and Ligand: First, the three-dimensional crystal structure of sPLA₂ was obtained and pretreated (removal of crystallographic water, addition of hydrogen atoms, and optimization of charge distribution); the molecular structure of Tris(2,4-di-tert-butylphenyl)phosphate was constructed and its conformation was optimized by energy minimization algorithm. The processed ligand was docked with the active site region of sPLA₂, and the program was run after setting docking parameters (including search space and binding mode screening criteria). After docking, the optimal conformation with the lowest binding energy was selected, and the interaction types (such as hydrogen bonds, hydrophobic interactions, van der Waals forces) between the ligand and amino acid residues in the enzyme's active site were analyzed to evaluate binding stability and specificity [1] |
| Animal Protocol | The acute anti-inflammatory activity of TDTBPP was assessed by Carrageenan-induced rat paw odema method. TDTBPP reduced the raw paw odema volume significantly at the tested doses of 50 mg/kg and 70 mg/kg body weight. Molecular docking studies were carried out with the X-ray crystal structures of Daboia russelli pulchella's (Vipera russelli, Indian Russell's viper) venom sPLA(2) and Human non-pancreatic secretory PLA(2) (Hnps PLA(2)) as targets to illustrate the antiinflammatory and antidote activities of TDTBPP. Docking results showed hydrogen bond (H-bond) interaction with Lys69 residue lying in the anti-coagulant loop of D. russelli's venom PLA(2), which is essential in the catalytic activity of the enzyme and hydrophobic interactions with the residues at the binding site (His48, Asp49). Docking of TDTBPP with Hnps PLA(2) structure showed coordination with calcium ion directly as well as through the catalytically important water molecule (HOH1260) located at the binding site[1]. |
| References |
[1]. Active compound from the leaves of Vitex negundo L. shows anti-inflammatory activity with evidence of inhibition for secretory Phospholipase A(2) through molecular docking. Bioinformation. 2011;7(4):199-206. |
| Additional Infomation |
Tris(2,4-di-tert-butylphenyl) phosphate is an aryl phosphate. Drug Source: Tris(2,4-di-tert-butylphenyl)phosphate is a natural active compound isolated and identified from the leaf extract of Vitex negundo L. [1] - Anti-Inflammatory Mechanism Background: sPLA₂ is a key regulatory enzyme in the inflammatory response. It releases arachidonic acid by hydrolyzing cell membrane phospholipids, which is further metabolized to produce pro-inflammatory mediators such as prostaglandins and leukotrienes. By targeting the active site of sPLA₂, this compound inhibits the enzyme's catalytic activity, blocks the inflammatory mediator synthesis pathway, and thus exerts anti-inflammatory effects [1] - Molecular Binding Characteristics: Docking results showed that Tris(2,4-di-tert-butylphenyl)phosphate forms 3 hydrogen bonds and multiple hydrophobic interactions with key amino acid residues in the active center of sPLA₂, allowing it to bind tightly to the enzyme's substrate-binding pocket and directly interfere with the binding efficiency between the substrate and the enzyme [1] |
Solubility Data
| Solubility (In Vitro) | Ethanol : ~100 mg/mL (~150.85 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.5 mg/mL (3.77 mM) in 10% EtOH + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH 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 (3.77 mM) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear EtOH 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 (3.77 mM) (saturation unknown) in 10% EtOH + 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 EtOH 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 | 1.5085 mL | 7.5424 mL | 15.0848 mL | |
| 5 mM | 0.3017 mL | 1.5085 mL | 3.0170 mL | |
| 10 mM | 0.1508 mL | 0.7542 mL | 1.5085 mL |