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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21158685
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21158685
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: Q9NZQ8 Gene ID: 29850.0 Gene Symbol: TRPM5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/21158685 |
12.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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[Synthesis, structure characterization and, fluorescence studies of the complexes of europium with phenylglyoxylic acid, 1,10-phenanthroline and triphenyl phosphine oxide]. | 2005 Dec |
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The coordination of perrhenate and pertechnetate to thorium(IV) in the presence of phosphine oxide or phosphate ligands. | 2006 Dec 28 |
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A columnar liquid crystal based on triphenylphosphine oxide--its structural changes upon interaction with alkaline metal cations. | 2006 Mar 28 |
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Novel stoichiometrically erbium-ytterbium cocrystalline complex exhibiting enhanced near-infrared luminescence. | 2006 May 29 |
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Determination of triphenylphosphine oxide in active pharmaceutical ingredients by hollow-fiber liquid-phase microextraction followed by reversed-phase liquid chromatography. | 2006 Sep 15 |
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Design of biotin-functionalized luminescent quantum dots. | 2007 |
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Complexes of Pd(II) and Pt(II) with 9-aminoacridine: reactions with DNA and study of their antiproliferative activity. | 2007 |
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Liquid chromatography/tandem mass spectrometry determination of organophosphorus flame retardants and plasticizers in drinking and surface waters. | 2007 |
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Synthesis, structures, and properties of meso-phosphorylporphyrins: self-organization through P-oxo-zinc coordination. | 2007 |
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An unexpected co-crystal with a variable degree of order: 1:1 rac-1,2-cyclohexanediol/triphenylphosphine oxide. | 2007 Dec |
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Identification of estrogenic compounds emitted from the combustion of computer printed circuit boards in electronic waste. | 2007 Dec 15 |
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Bis(2-benzoyl-1-phenyl-ethenolato-κO,O')(ethanol-κO)dioxidouranium(VI). | 2007 Dec 18 |
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Well-defined silica-supported rare-earth silylamides. | 2007 Feb 19 |
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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 Jul |
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Multiporphyrin coordination arrays based on complexation of magnesium(II) porphyrins with porphyrinylphosphine oxides. | 2007 Jun 7 |
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Study of the interaction between oxygen and bile salts. | 2007 May |
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A novel tetrakis(pyrazolyl)borate ligand bearing triphenylphosphine oxide substituents. | 2007 Nov 14 |
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Determination of peroxide value of edible oils by FTIR spectroscopy with the use of the spectral reconstitution technique. | 2007 Nov 30 |
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Determination of NMR interaction parameters from double rotation NMR. | 2007 Oct |
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Configurationally stable propeller-like triarylphosphine and triarylphosphine oxide. | 2007 Sep 28 |
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The synthesis of 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose, and their evaluation as nutritional supplements for pre-term infants. | 2007 Sep 3 |
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Comparison of the electrochemical and luminescence properties of two carbazole-based phosphine oxide Eu(III) complexes: effect of different bipolar ligand structures. | 2008 Aug 25 |
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trans-Tetra-iodidobis(tri-p-tolyl-phosphine oxide-κO)tin(IV). | 2008 Aug 6 |
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(3-Amino-phen-yl)diphenyl-phosphine oxide-2-propanol (1/1). | 2008 Feb 22 |
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A reactivity change of a strontium monohydroxide by umpolung to an acid. | 2008 Jul 7 |
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3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid-triphenyl-phosphine oxide (1/1). | 2008 Jul 9 |
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Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols. | 2008 Mar 19 |
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2-(4-Bromo-phen-oxy)-3-isopropyl-5,6,7,8-tetra-hydro-1-benzothieno[2,3-d]pyrimidin-4(3H)-one. | 2008 Nov 22 |
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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 Nov 26 |
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Circularly polarized luminescence of Eu(III) complexes with point- and axis-chiral ligands dependent on coordination structures. | 2009 Dec 7 |
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Determination of hydroperoxide content in complex hydrocarbon mixtures by gas chromatography/mass spectrometry. | 2009 Mar |
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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 Mar 2 |
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[Study on photoluminescence of 2-(4-chloro-benzoyl)benzoic acid complexes]. | 2009 Nov |
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3-Isopropyl-2-(4-methoxy-phen-oxy)-1-benzo-furo[3,2-d]pyrimidin-4(3H)-one. | 2009 Oct 23 |
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Triphenyl-phosphine oxide-2-(4-hydroxy-benzen-yl)-4,4,5,5-tetra-methyl-imidazolidine-1-oxyl 3-oxide (1/1). | 2009 Sep 12 |
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Calcium-centred phosphine oxide reactivity: P-C metathesis, reduction and P-P coupling. | 2010 Apr 14 |
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Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products. | 2010 Apr 14 |
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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 Apr 17 |
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Diiodidobis(triphenyl-phosphine oxide)cadmium. | 2010 Dec 24 |
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Aqueous dispersion of conjugated polymers by colloidal clays and their film photoluminescence. | 2010 Feb 11 |
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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 Feb 26 |
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Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. | 2010 Jan |
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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 Jul |
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Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010 Jul 30 |
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Grafting of lanthanide complexes on silica surfaces: a theoretical investigation. | 2010 Jun 3 |
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A simplified UV spectrometric method for determination of peroxide value in thermally oxidized canola oil. | 2010 Mar 15 |
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Tris{N-[bis-(dimethyl-amino)phosphino-yl]-2,2,2-trichloro-acetamido}(triphenyl-phosphine oxide)holmium(III). | 2010 May 12 |
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The reaction chemistry of plutonyl(VI) chloride complexes with triphenyl phosphineoxide and triphenyl phosphinimine. | 2010 Oct 18 |
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Investigation of Lewis acid versus Lewis base catalysis in asymmetric cyanohydrin synthesis. | 2010 Oct 4 |
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Mass spectrometric characterization of metal triflates and triflimides (Lewis superacid catalysts) by electrospray ionization and tandem mass spectrometry. | 2010 Sep 15 |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21158685
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
Fri Dec 15 19:40:55 GMT 2023
by
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on
Fri Dec 15 19:40:55 GMT 2023
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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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398
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TRIPHENYLPHOSPHINE OXIDE
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1478833
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DTXSID2022121
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