| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Mitochondrial metabolism; succinate dehydrogenase (SDH, respiratory complex II); carnitine palmitoyltransferase 1 (CPT1); human GPR84 receptor.
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|---|---|
| ln Vitro |
Diphenyl Phosphate inhibits the activity of SDH (succinate dehydrogenase, respiratory complex II), reduces the expression of CPT1 (carnitine palmitoyltransferase 1), and disrupts mitochondrial membrane integrity. It shows antagonist activity at human GPR84 receptors expressed in HEK293 cells, as measured by reduction in intracellular calcium response induced by 6-OAU. The compound inhibits oxidative phosphorylation, a crucial process in cellular respiration that generates ATP.
|
| ln Vivo |
DPhP inhibits growth and energy metabolism in zebrafish in a sex-specific manner. In adult mice, neonatal exposure to DPhP induces sex- and dose-dependent metabolic disruptions. The compound can cross the blood-brain barrier and induce neurotoxic effects in mice. It affects mRNA expression in chicken embryonic hepatocytes and induces metabolic disruptions and toxicity during embryonic development.
|
| Enzyme Assay |
GPR84 receptor antagonist activity is evaluated using HEK293 cells expressing human GPR84. Cells are preincubated with Diphenyl Phosphate for 10 minutes before the addition of the agonist 6-OAU. Intracellular calcium response is measured using a fluorescence-based calcium assay. The reduction in calcium signal indicates antagonist activity. For enzyme inhibition studies, SDH activity is measured spectrophotometrically in mitochondrial preparations. CPT1 expression is quantified by Western blot or qPCR.
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| Cell Assay |
For cell-based studies, HEK293 cells expressing human GPR84 receptors are cultured in appropriate medium. Cells are seeded in 96-well plates and loaded with calcium-sensitive fluorescent dye. Test compound is added at various concentrations and incubated for 10 minutes. The agonist 6-OAU is then added and the intracellular calcium response is measured using a fluorescence plate reader. The inhibitory effect of Diphenyl Phosphate on the calcium response is calculated relative to control wells.
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| Animal Protocol |
In zebrafish studies, embryos or adult fish are exposed to environmentally relevant concentrations of DPhP in aquarium water. Growth parameters, energy metabolism markers, and sex-specific responses are assessed over the life cycle. In mouse studies, neonatal mice are exposed to DPhP via oral administration or injection. Metabolic disruptions are evaluated by measuring body weight, metabolic markers, and tissue analysis. Tissue samples are collected for histopathological examination and biochemical analysis.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for DPhP are primarily derived from its role as a TPHP metabolite. DPhP is detected in human urine as a biomarker of TPHP exposure. It is moderately soluble in organic solvents such as ethanol and acetone but practically insoluble in water. The compound is amenable to HPLC-MS analysis for pharmacokinetic studies. As an environmental contaminant, DPhP can accumulate in organisms and exhibits sex-specific effects on metabolism.
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| Toxicity/Toxicokinetics |
Diphenyl phosphate is considered to have low acute toxicity but may pose chronic health risks upon prolonged exposure. Inhalation or skin contact may cause mild irritation to the respiratory tract and dermal tissues. In zebrafish, DPhP inhibits growth and energy metabolism in a sex-specific manner. Neonatal exposure in mice induces metabolic disruptions. The compound can cross the blood-brain barrier and induce neurotoxic effects. Standard safety precautions should be taken when handling this compound.
|
| References |
[1]. Chen Q, et al. Life Cycle Exposure to Environmentally Relevant Concentrations of Diphenyl Phosphate (DPhP) Inhibits Growth and Energy Metabolism of Zebrafish in a Sex-Specific Manner. Environ Sci Technol. 2021 Oct 5;55(19):13122-13131.
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| Additional Infomation |
Diphenyl phosphate is an aryl phosphate ester.
Diphenyl Phosphate is primarily used as an analytical standard and research tool for studying the metabolism and toxicity of organophosphate flame retardants. It serves as a biomarker of exposure to triphenyl phosphate and other aryl phosphate esters. The compound's sex-specific effects on energy metabolism make it valuable for studying metabolic diseases and endocrine disruption. It is intended for research use only, not for therapeutic or human use. |
| Molecular Formula |
C12H11O4P
|
|---|---|
| Molecular Weight |
250.19
|
| Exact Mass |
250.039
|
| CAS # |
838-85-7
|
| Related CAS # |
Diphenyl Phosphate-d10;1477494-97-5
|
| PubChem CID |
13282
|
| Appearance |
White to off-white solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
377.7±25.0 °C at 760 mmHg
|
| Melting Point |
62-66 °C(lit.)
|
| Flash Point |
182.3±23.2 °C
|
| Vapour Pressure |
0.0±0.9 mmHg at 25°C
|
| Index of Refraction |
1.588
|
| LogP |
1.34
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
17
|
| Complexity |
246
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=P(OC1C=CC=CC=1)(OC1C=CC=CC=1)O
|
| InChi Key |
ASMQGLCHMVWBQR-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C12H11O4P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H,(H,13,14)
|
| Chemical Name |
diphenyl hydrogen phosphate
|
| 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)
|
| Solubility (In Vitro) |
DMSO: ≥ 100 mg/mL (399.70 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (9.99 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 (9.99 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (9.99 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.9970 mL | 19.9848 mL | 39.9696 mL | |
| 5 mM | 0.7994 mL | 3.9970 mL | 7.9939 mL | |
| 10 mM | 0.3997 mL | 1.9985 mL | 3.9970 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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