Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C18H15OP |
| Molecular Weight | 278.2849 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
InChI
InChIKey=FIQMHBFVRAXMOP-UHFFFAOYSA-N
InChI=1S/C18H15OP/c19-20(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18/h1-15H
| Molecular Formula | C18H15OP |
| Molecular Weight | 278.2849 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Triphenylphosphine oxide (TPPO) is a neurotoxic very stable polar compound present in waste organic solutions from the chemical and pharmaceutical industry. The acute toxicity of TPPO LC50=12.2µg/mL, LC90=29.5µg/mL is higher than triphenyltin acetate so that a correct management in the relationship with sustainable chemistry is strongly required. TPPO was identified as a selective and potent inhibitor of transient receptor potential melastatin-5 (TRPM5), but at the same moment, it had no effect (up to 100 μM) on the membrane potential responses of TRPA1, TRPV1, or TRPM4b.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Diiodidobis(triphenyl-phosphine oxide)cadmium. | 2010-12-24 |
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| Triphenylphosphine oxide is a potent and selective inhibitor of the transient receptor potential melastatin-5 ion channel. | 2010-12 |
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| The reaction chemistry of plutonyl(VI) chloride complexes with triphenyl phosphineoxide and triphenyl phosphinimine. | 2010-10-18 |
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| Investigation of Lewis acid versus Lewis base catalysis in asymmetric cyanohydrin synthesis. | 2010-10-04 |
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| Mass spectrometric characterization of metal triflates and triflimides (Lewis superacid catalysts) by electrospray ionization and tandem mass spectrometry. | 2010-09-15 |
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| Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010-07-30 |
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| [Study on synthesis and fluorescence characterization of europium and terbium complexes of 1-(5-(2-hydroxyphenyl)-3-methyl-4,5-dihydropyrazol-1-yl) ethanone]. | 2010-07 |
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| Grafting of lanthanide complexes on silica surfaces: a theoretical investigation. | 2010-06-03 |
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| Tris{N-[bis-(dimethyl-amino)phosphino-yl]-2,2,2-trichloro-acetamido}(triphenyl-phosphine oxide)holmium(III). | 2010-05-12 |
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| catena-Poly[[[aqua-copper(II)]bis-[μ-bis(3,5-dimethyl-1H-pyrazol-4-yl) selenide]] bis-(tetra-fluorido-borate) bis-(triphenyl-phosphine oxide) monohydrate]. | 2010-04-17 |
|
| Calcium-centred phosphine oxide reactivity: P-C metathesis, reduction and P-P coupling. | 2010-04-14 |
|
| Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products. | 2010-04-14 |
|
| A simplified UV spectrometric method for determination of peroxide value in thermally oxidized canola oil. | 2010-03-15 |
|
| Mixed-mode solid-phase extraction followed by liquid chromatography-tandem mass spectrometry for the determination of tri- and di-substituted organophosphorus species in water samples. | 2010-02-26 |
|
| Aqueous dispersion of conjugated polymers by colloidal clays and their film photoluminescence. | 2010-02-11 |
|
| Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. | 2010-01 |
|
| Circularly polarized luminescence of Eu(III) complexes with point- and axis-chiral ligands dependent on coordination structures. | 2009-12-07 |
|
| [Study on photoluminescence of 2-(4-chloro-benzoyl)benzoic acid complexes]. | 2009-11 |
|
| 3-Isopropyl-2-(4-methoxy-phen-oxy)-1-benzo-furo[3,2-d]pyrimidin-4(3H)-one. | 2009-10-23 |
|
| Triphenyl-phosphine oxide-2-(4-hydroxy-benzen-yl)-4,4,5,5-tetra-methyl-imidazolidine-1-oxyl 3-oxide (1/1). | 2009-09-12 |
|
| A study on the near-infrared luminescent properties of xerogel materials doped with dysprosium complexes. | 2009-09-07 |
|
| Automated and simultaneous determination of free fatty acids and peroxide values in edible oils by FTIR spectroscopy using spectral reconstitution. | 2009-05 |
|
| Synthesis and characterization of a new metal-organic NLO material: dibromo bis(triphenylphosphine oxide) mercury(II). | 2009-05 |
|
| What a difference a 5f element makes: trivalent and tetravalent uranium halide complexes supported by one and two bis[2-(diisopropylphosphino)-4-methylphenyl]amido (PNP) ligands. | 2009-03-02 |
|
| Determination of hydroperoxide content in complex hydrocarbon mixtures by gas chromatography/mass spectrometry. | 2009-03 |
|
| Complex formation of uranyl ion with triphenylphosphine oxide and its ligand exchange reaction in 1-butyl-3-methylimidazolium nonafluorobutanesulfonate ionic liquid. | 2009-02-16 |
|
| Enantioselective cyanosilylation of ketones catalyzed by recyclable polymeric and dimeric Mn(III) salen complexes at room temperature. | 2009-02 |
|
| [Study on synthesis, structure characterization and fluorescence of europium complexes of 2-(4-fluorobenzoyl) benzoic acid]. | 2009-01 |
|
| 3-Phenyl-2-(piperidin-1-yl)-3,5,6,8-tetra-hydro-4H-thio-pyrano[3',4':2,3]thieno[5,4-d]pyrimidin-4-one. | 2008-11-26 |
|
| 2-(4-Bromo-phen-oxy)-3-isopropyl-5,6,7,8-tetra-hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one. | 2008-11-22 |
|
| Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane. | 2008-09-28 |
|
| Formation of brown lines in paper: characterization of cellulose degradation at the wet-dry interface. | 2008-09 |
|
| Comparison of the electrochemical and luminescence properties of two carbazole-based phosphine oxide Eu(III) complexes: effect of different bipolar ligand structures. | 2008-08-25 |
|
| trans-Tetra-iodidobis(tri-p-tolyl-phosphine oxide-κO)tin(IV). | 2008-08-06 |
|
| 3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid-triphenyl-phosphine oxide (1/1). | 2008-07-09 |
|
| A reactivity change of a strontium monohydroxide by umpolung to an acid. | 2008-07-07 |
|
| Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols. | 2008-03-19 |
|
| Improved luminescence properties of europium complexes encapsulated into mesoporous SBA-15. | 2008-03 |
|
| (3-Amino-phen-yl)diphenyl-phosphine oxide-2-propanol (1/1). | 2008-02-22 |
|
| Bis(2-benzoyl-1-phenyl-ethenolato-κO,O')(ethanol-κO)dioxidouranium(VI). | 2007-12-18 |
|
| Identification of estrogenic compounds emitted from the combustion of computer printed circuit boards in electronic waste. | 2007-12-15 |
|
| Bis(acetyl-acetonato)oxido(triphenyl-phosphine oxide)vanadium(IV). | 2007-12-12 |
|
| An unexpected co-crystal with a variable degree of order: 1:1 rac-1,2-cyclohexanediol/triphenylphosphine oxide. | 2007-12 |
|
| Determination of peroxide value of edible oils by FTIR spectroscopy with the use of the spectral reconstitution technique. | 2007-11-30 |
|
| A novel tetrakis(pyrazolyl)borate ligand bearing triphenylphosphine oxide substituents. | 2007-11-14 |
|
| Determination of NMR interaction parameters from double rotation NMR. | 2007-10 |
|
| Configurationally stable propeller-like triarylphosphine and triarylphosphine oxide. | 2007-09-28 |
|
| Optimisation of a selective method for the determination of organophosphorous triesters in outdoor particulate samples by pressurised liquid extraction and large-volume injection gas chromatography-positive chemical ionisation-tandem mass spectrometry. | 2007-07 |
|
| Design of biotin-functionalized luminescent quantum dots. | 2007 |
|
| Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity. | 2007 |
Sample Use Guides
Using recombinant transient receptor potential melastatin-5 (TRPM5) -expressing cells in a fluorescence imaging plate reader-based membrane potential assay, was identified triphenylphosphine oxide (TPPO) as a selective and potent inhibitor of TRPM5. TPPO inhibited both human (IC₅₀ = 12 μM) and murine TRPM5 (IC₅₀ = 30 μM) heterologously expressed in HEK293 cells, but had no effect (up to 100 μM) on the membrane potential responses of TRPA1, TRPV1, or TRPM4b. TPPO also inhibited a calcium-gated TRPM5-dependent conductance in taste cells isolated from the tongues of transgenic TRPM5(+/)⁻ mice.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:53:17 GMT 2025
by
admin
on
Mon Mar 31 19:53:17 GMT 2025
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| Record UNII |
Z69161FKI3
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| Record Status |
Validated (UNII)
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| Record Version |
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13097
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212-338-8
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398
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TRIPHENYLPHOSPHINE OXIDE
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1478833
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Z69161FKI3
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36601
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DTXSID2022121
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