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Bisphenol A bis(diphenyl phosphate)

Bisphenol A bis(diphenyl phosphate) is a flame retardant.
Bisphenol A bis(diphenyl phosphate)
Bisphenol A bis(diphenyl phosphate) Chemical Structure CAS No.: 5945-33-5
Product category: Biochemical Assay Reagents
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Bisphenol A bis (diphenyl phosphate) is a flame retardant. Besides its gas-phase effects, Bisphenol A bis (diphenyl phosphate) also exhibits important condensed-phase effects.
Bisphenol A bis(diphenyl phosphate) (BDP, CAS 5945-33-5) is a phosphoric ester flame retardant and plasticizer. It is also known as Bisphenol-A diphenyl phosphate or Bisphenol A bis(diphenyl phosphate). Its molecular formula is C39H34O8P2, with a molecular weight of 692.63 g/mol. This compound is a halogen-free, oligomeric phosphate ester widely used as an additive to improve the fire resistance of engineering thermoplastics (e.g., PPO/HIPS blends, PC/ABS, ABS, polycarbonate). In research, it is used as an analytical reference standard for environmental monitoring of organophosphate flame retardants. It is not a pharmaceutical drug; it is an industrial chemical.
Biological Activity I Assay Protocols (From Reference)
Targets
Bisphenol A bis(diphenyl phosphate) is an industrial flame retardant. It does not have a specific biological target for therapeutic purposes. Its mechanism of action is physical/chemical: it decomposes to release phosphoric acid, which promotes char formation (condensed phase action) and acts as a radical scavenger in the gas phase. Toxicologically, it is being studied as an environmental contaminant and potential endocrine disruptor (weak estrogenic activity due to bisphenol A backbone). It may bind weakly to the estrogen receptor (ER) at very high concentrations, but this is an off-target effect, not a therapeutic target.
ln Vitro
In vitro, BDP is not used for biological activity studies. It is an analytical standard. In an HPLC method, it is dissolved in acetonitrile (1 mg/mL). Calibration standards are prepared at 0.1-50 ug/mL. It is used to quantify BDP in polymer leachates or dust samples for environmental exposure assessment. It may show weak estrogenic activity in an MCF-7 cell proliferation assay (E-SCREEN) at high concentrations (>10 uM). It is also a plasticizer, used to melt-process polycarbonate/acrylonitrile-butadiene-styrene (PC/ABS) blends. It is not used for drug screening.
ln Vivo
In vivo, BDP is not administered for therapeutic purposes. It is used in animal studies to investigate the toxicokinetics and bioaccumulation of organophosphate flame retardants. In a 28-day oral feeding study in rats (e.g., 50-200 mg/kg/day), BDP may cause liver enlargement (hepatomegaly) and increased activity of liver enzymes (ALT, AST). It is not used in efficacy models. It is an industrial chemical used in plastics manufacturing.
Enzyme Assay
General protocol for in vitro analytical use: For HPLC analysis of flame retardants, prepare a 1 mg/mL stock solution in acetonitrile. Prepare calibration standards in acetonitrile at 0.1, 0.5, 1, 5, 10, 25, 50, 100 ug/mL. Use a C18 column (4.6 × 150 mm, 5 um) with mobile phase acetonitrile:water (70:30) at 1.0 mL/min. UV detection at 230 nm. For sample preparation, extract dust (100 mg) with 10 mL acetonitrile, sonicate, filter, and inject 20 uL. For LC-MS, use positive mode with m/z 693 [M+H]+. Store the compound at room temperature.
Cell Assay
General protocol for in vitro cell-based experiments: For an estrogenicity assay, culture MCF-7 cells in phenol red-free DMEM with 10% charcoal-stripped FBS. Seed in 96-well plates (1×10^4 cells/well). Treat with BDP (0.1-100 uM) for 48 h. Measure cell proliferation by MTT. Include 1 nM 17beta-estradiol as a positive control. BDP may show weak proliferative effects only at >10 uM. This is a toxicological assessment.
Animal Protocol
General protocol for in vivo animal experiments: For a toxicokinetic study, administer BDP (100 mg/kg, oral) in corn oil to male Sprague-Dawley rats (n=5). Collect blood at 0, 1, 2, 4, 8, 12, 24, 48 h. Extract plasma with ethyl acetate, evaporate, reconstitute, and analyze by HPLC-UV. The half-life is expected to be 6-12 hours. This study assesses systemic exposure, not therapeutic efficacy.
ADME/Pharmacokinetics
General pharmacokinetic properties: This compound (MW 692.63) is a high molecular weight, lipophilic solid or viscous liquid (LogP >5). It is insoluble in water but soluble in organic solvents. If absorbed, it would be metabolized by CYP450 enzymes (hydrolysis) to bisphenol A and diphenyl phosphate. Elimination half-life may be long (days) due to high lipophilicity. For storage, it is supplied as a solid or liquid, kept at room temperature in a sealed container. Stock solutions in acetonitrile are stable at -20degC for 6 months.
Toxicity/Toxicokinetics
General toxicity profile: BDP is a potential endocrine disruptor (weak estrogenicity) and may be toxic to aquatic life. It is an irritant. The oral LD50 in rats is >5000 mg/kg. Standard safety precautions (gloves, lab coat, fume hood) should be used. GHS hazard statements may include H411 (Toxic to aquatic life with long-lasting effects). For research use only.
References

[1]. Flame retardancy mechanisms of triphenyl phosphate, resorcinol bis(diphenyl phosphate) and bisphenol A bis(diphenyl phosphate) in polycarbonate/acrylonitrile-butadiene-styrene blends. Polymer International. 27 June 2007.

Additional Infomation
Bisphenol A bis(diphenyl phosphate) is also known as BDP, BPADP, or Aflammit PLF 100. It is a halogen-free flame retardant used as a replacement for brominated flame retardants. Its molecular formula is C39H34O8P2. The product is for research, analytical, and forensic use only, not for human consumption. Store in a cool, dry place.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C39H34O8P2
Molecular Weight
692.63
Exact Mass
692.173
CAS #
5945-33-5
PubChem CID
9874825
Appearance
Typically exists as solids at room temperature
Hydrogen Bond Donor Count
0
Rotatable Bond Count
14
Heavy Atom Count
49
Complexity
931
Defined Atom Stereocenter Count
0
SMILES
CC(C)(C1=CC=C(C=C1)OP(=O)(OC2=CC=CC=C2)OC3=CC=CC=C3)C4=CC=C(C=C4)OP(=O)(OC5=CC=CC=C5)OC6=CC=CC=C6
InChi Key
BQPNUOYXSVUVMY-UHFFFAOYSA-N
InChi Code
InChI=1S/C39H34O8P2/c1-39(2,31-23-27-37(28-24-31)46-48(40,42-33-15-7-3-8-16-33)43-34-17-9-4-10-18-34)32-25-29-38(30-26-32)47-49(41,44-35-19-11-5-12-20-35)45-36-21-13-6-14-22-36/h3-30H,1-2H3
Chemical Name
[4-[2-(4-diphenoxyphosphoryloxyphenyl)propan-2-yl]phenyl] diphenyl phosphate
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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 1.4438 mL 7.2189 mL 14.4377 mL
5 mM 0.2888 mL 1.4438 mL 2.8875 mL
10 mM 0.1444 mL 0.7219 mL 1.4438 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:

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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)
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  • 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:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

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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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