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Triphenylmethanol

Triphenylmethanol
Triphenylmethanol Chemical Structure CAS No.: 76-84-6
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
Triphenylmethanol (CAS: 76-84-6), also known as Trt-OH or triphenylcarbinol, is an organic compound with the molecular formula C1₉H1₆O and molecular weight 260.33 g/mol. It is a triarylmethane derivative where a central carbon atom is bonded to three phenyl rings and a hydroxyl group. Triphenylmethanol is a white to off-white crystalline powder with a melting point of 160-163degC and a boiling point of 360degC at 760 mmHg. It is widely used as a reagent in research laboratories, serving as an intermediate in the production of triarylmethane dyes and as a precursor for the synthesis of triphenylmethyl (trityl) protecting groups, which are essential in peptide and nucleotide chemistry for selectively protecting reactive hydroxyl groups. It is also identified as Zidovudine EP Impurity D, serving as a reference standard for pharmaceutical impurity testing.
Biological Activity I Assay Protocols (From Reference)
Targets
This compound does not have a defined pharmacological target in biological systems, as it is primarily a chemical reagent and synthetic intermediate with no therapeutic applications. However, triphenylmethanol has been shown to inhibit neoplastic transformation of cells, suggesting potential antiproliferative properties. Its mechanism of action in this context is not well understood but may relate to its ability to act as a specific clathrate host for methanol and dimethyl sulfoxide (DMSO) and to form molecular complexes with various small molecules. The triphenylmethyl (trityl) carbocation is a stable, resonance-stabilized species that can participate in various chemical reactions, but this chemistry does not translate directly to defined biological targets.
ln Vitro
In vitro, triphenylmethanol has been shown to inhibit neoplastic transformation of cells, indicating antiproliferative activity. While the precise IC₅0 values are not widely reported in the literature, the compound has been studied for its ability to prevent the transformation of normal cells into tumor cells in culture-based transformation assays. In standard proliferation assays using cancer cell lines, triphenylmethanol and its derivatives have demonstrated moderate cytotoxic effects. The compound also exhibits the ability to form inclusion complexes (clathrates) with small guest molecules such as methanol and DMSO, which can be exploited for separation and purification applications in analytical chemistry.
ln Vivo
In vivo activity of triphenylmethanol has not been extensively characterized, as it is not a drug candidate. The compound is primarily used as a chemical reagent and synthetic intermediate rather than for therapeutic evaluation in animal models. Triphenylmethanol is known to be a combustion hazard (combustible solid) and may release irritating and toxic fumes (carbon monoxide, carbon dioxide) upon decomposition under fire conditions. It has no known therapeutic applications in animals or humans. The compound is not intended for in vivo administration in any medical context.
Enzyme Assay
Non-cellular (cell-free) experiments with triphenylmethanol are primarily chemical in nature. A typical protocol for using triphenylmethanol as a clathrate host for methanol separation involves dissolving triphenylmethanol in a suitable organic solvent and crystallizing it in the presence of methanol, where it forms a 1:1 inclusion complex. For analytical purposes, HPLC methods for monitoring triphenylmethanol content use a C18 reverse-phase column with a mobile phase of acetonitrile and water (70:30 v/v) at a flow rate of 1.0 mL/min, with UV detection at 254 nm. The compound is soluble in alcohol, ether, and benzene, but is insoluble in water.
Cell Assay
Cell-based experiments for triphenylmethanol are typically conducted to evaluate its antiproliferative and anti-neoplastic transformation properties. A standard protocol for transformation assays uses mouse C3H10T1/2 fibroblasts (an embryonic mesenchymal cell line). Cells are seeded at low density in 6-well plates and cultured in DMEM supplemented with 10% fetal bovine serum. The following day, cells are treated with triphenylmethanol at concentrations ranging from 1 to 100 microM, with or without exposure to a chemical carcinogen (e.g., 3-methylcholanthrene). After 5-7 days, cells are fixed with methanol, stained with Giemsa stain, and transformed foci are scored under an inverted microscope. The number of Type II and Type III foci is counted, representing the extent of neoplastic transformation inhibition. For viability assessment, MTT assays can be performed.
Animal Protocol
In vivo animal experiments are not typically conducted for triphenylmethanol, as it is a research chemical with no therapeutic indication. However, toxicological evaluations may be performed for safety assessment. A standard acute oral toxicity study in Sprague-Dawley rats would involve a single oral gavage dose of triphenylmethanol (e.g., 500, 1000, 2000 mg/kg) suspended in corn oil or 0.5% methylcellulose. Animals are observed for 14 days for signs of toxicity, mortality, and body weight changes. At study termination, necropsy is performed, and organs (liver, kidneys, heart, lungs, spleen) are examined for gross abnormalities. Histopathological examination may be conducted. Triphenylmethanol may cause irritation of the digestive tract and respiratory tract irritation upon inhalation.
ADME/Pharmacokinetics
Pharmacokinetic properties of triphenylmethanol are not well characterized, as it is a chemical reagent rather than a drug candidate. Based on its physicochemical properties (logP approximately 4-5, molecular weight 260.33), it is a lipophilic compound that would be expected to undergo extensive metabolism by cytochrome P450 enzymes if absorbed. The compound is practically insoluble in water (solubility <0.01 mg/mL) but soluble in organic solvents such as ethanol, diethyl ether, benzene, and acetone. It is stable under normal laboratory conditions (room temperature, inert atmosphere) but sensitive to strong oxidizing agents, strong acids, and light. When dissolved in concentrated sulfuric acid, it turns dark yellow, while it remains colorless when dissolved in glacial acetic acid.
Toxicity/Toxicokinetics
The toxicological properties of triphenylmethanol have not been fully investigated. Available GHS hazard classifications indicate that triphenylmethanol causes skin irritation (H315) with >98% of notifications reporting this hazard. It may cause serious eye irritation (H319) and may cause respiratory tract irritation (H335) (Specific Target Organ Toxicity, single exposure, Category 3). Acute oral toxicity data are not available. Chronic effects may include dermatitis and asthma-like symptoms upon prolonged or repeated exposure. As a combustible solid, it should be kept away from sources of ignition. The compound has a water hazard class (WGK) of 3, indicating it is hazardous to water. Decomposition products upon combustion include carbon monoxide, carbon dioxide, and irritating and toxic fumes and gases.
References

[1]. Inhibition of cellular transformation by triphenylmethane: a novel chemopreventive agent. Carcinogenesis. 1992 Jul;13(7):1107-12.

[2]. Specific entrapment of methanol and dimethyl sulphoxide (DMSO) by a simple host compound (triphenylmethanol). Crystal structures of the Ph 3 COH• MeOH (1: 1) and Ph 3 COH• DMSO (2: 1) clathrate inclusion complexes. Journal of the Chemical Society, Chemical Communications, 1989 (17): 1195-1197.

Additional Infomation
Additional information: Triphenylmethanol is a white powder or colorless isolated crystals with a density of 1.199 at 40degC (d40). Its IUPAC name is triphenylmethanol. It has an EC number of 200-988-5 and RTECS number of DC1850000. The compound is soluble in alcohol, ether, benzene, and glacial acetic acid, and insoluble in water and petroleum ether. It is stable under normal temperatures and pressures but is incompatible with oxidizing agents, acids, acid chlorides, and acid anhydrides. Triphenylmethanol is frequently employed as a reactant in the formation of esters, ethers, and other functionalized compounds through various chemical transformations including esterification and Grignard reactions. It is a versatile compound used in organic synthesis as a protecting group reagent (trityl chloride is derived from triphenylmethanol) and as a standard for chromatographic analysis.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H16O
Molecular Weight
260.34
Exact Mass
260.12
CAS #
76-84-6
PubChem CID
6457
Appearance
Typically exists as solids at room temperature
Hydrogen Bond Donor Count
1
Rotatable Bond Count
3
Heavy Atom Count
20
Complexity
235
Defined Atom Stereocenter Count
0
SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)O
InChi Key
LZTRCELOJRDYMQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H16O/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15,20H
Chemical Name
triphenylmethanol
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 3.8411 mL 19.2057 mL 38.4113 mL
5 mM 0.7682 mL 3.8411 mL 7.6823 mL
10 mM 0.3841 mL 1.9206 mL 3.8411 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:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
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)
  • Click the “Calculate” button
  • 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:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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