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 |
|---|---|---|
| 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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| 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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| 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 |
|
| Well-defined silica-supported rare-earth silylamides. | 2007 Feb 19 |
|
| 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 |
|
| Multiporphyrin coordination arrays based on complexation of magnesium(II) porphyrins with porphyrinylphosphine oxides. | 2007 Jun 7 |
|
| Study of the interaction between oxygen and bile salts. | 2007 May |
|
| A novel tetrakis(pyrazolyl)borate ligand bearing triphenylphosphine oxide substituents. | 2007 Nov 14 |
|
| Determination of peroxide value of edible oils by FTIR spectroscopy with the use of the spectral reconstitution technique. | 2007 Nov 30 |
|
| Determination of NMR interaction parameters from double rotation NMR. | 2007 Oct |
|
| Configurationally stable propeller-like triarylphosphine and triarylphosphine oxide. | 2007 Sep 28 |
|
| 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 |
|
| 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 |
|
| trans-Tetra-iodidobis(tri-p-tolyl-phosphine oxide-κO)tin(IV). | 2008 Aug 6 |
|
| (3-Amino-phen-yl)diphenyl-phosphine oxide-2-propanol (1/1). | 2008 Feb 22 |
|
| A reactivity change of a strontium monohydroxide by umpolung to an acid. | 2008 Jul 7 |
|
| 3-Chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid-triphenyl-phosphine oxide (1/1). | 2008 Jul 9 |
|
| Improved luminescence properties of europium complexes encapsulated into mesoporous SBA-15. | 2008 Mar |
|
| Vinylation of aromatic halides using inexpensive organosilicon reagents. Illustration of design of experiment protocols. | 2008 Mar 19 |
|
| 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 |
|
| 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 |
|
| Formation of brown lines in paper: characterization of cellulose degradation at the wet-dry interface. | 2008 Sep |
|
| Lewis base-catalyzed conjugate reduction and reductive aldol reaction of alpha,beta-unsaturated ketones using trichlorosilane. | 2008 Sep 28 |
|
| Circularly polarized luminescence of Eu(III) complexes with point- and axis-chiral ligands dependent on coordination structures. | 2009 Dec 7 |
|
| Enantioselective cyanosilylation of ketones catalyzed by recyclable polymeric and dimeric Mn(III) salen complexes at room temperature. | 2009 Feb |
|
| Complex formation of uranyl ion with triphenylphosphine oxide and its ligand exchange reaction in 1-butyl-3-methylimidazolium nonafluorobutanesulfonate ionic liquid. | 2009 Feb 16 |
|
| [Study on synthesis, structure characterization and fluorescence of europium complexes of 2-(4-fluorobenzoyl) benzoic acid]. | 2009 Jan |
|
| Determination of hydroperoxide content in complex hydrocarbon mixtures by gas chromatography/mass spectrometry. | 2009 Mar |
|
| Automated and simultaneous determination of free fatty acids and peroxide values in edible oils by FTIR spectroscopy using spectral reconstitution. | 2009 May |
|
| Synthesis and characterization of a new metal-organic NLO material: dibromo bis(triphenylphosphine oxide) mercury(II). | 2009 May |
|
| [Study on photoluminescence of 2-(4-chloro-benzoyl)benzoic acid complexes]. | 2009 Nov |
|
| 3-Isopropyl-2-(4-methoxy-phen-oxy)-1-benzo-furo[3,2-d]pyrimidin-4(3H)-one. | 2009 Oct 23 |
|
| Triphenyl-phosphine oxide-2-(4-hydroxy-benzen-yl)-4,4,5,5-tetra-methyl-imidazolidine-1-oxyl 3-oxide (1/1). | 2009 Sep 12 |
|
| A study on the near-infrared luminescent properties of xerogel materials doped with dysprosium complexes. | 2009 Sep 7 |
|
| Calcium-centred phosphine oxide reactivity: P-C metathesis, reduction and P-P coupling. | 2010 Apr 14 |
|
| Enantioselective ProPhenol-catalyzed addition of 1,3-diynes to aldehydes to generate synthetically versatile building blocks and diyne natural products. | 2010 Apr 14 |
|
| 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 |
|
| Diiodidobis(triphenyl-phosphine oxide)cadmium. | 2010 Dec 24 |
|
| Aqueous dispersion of conjugated polymers by colloidal clays and their film photoluminescence. | 2010 Feb 11 |
|
| 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 |
|
| Mass spectrometric analyses of organophosphate insecticide oxon protein adducts. | 2010 Jan |
|
| Chemoreception regulates chemical access to mouse vomeronasal organ: role of solitary chemosensory cells. | 2010 Jul 30 |
|
| Grafting of lanthanide complexes on silica surfaces: a theoretical investigation. | 2010 Jun 3 |
|
| A simplified UV spectrometric method for determination of peroxide value in thermally oxidized canola oil. | 2010 Mar 15 |
|
| Tris{N-[bis-(dimethyl-amino)phosphino-yl]-2,2,2-trichloro-acetamido}(triphenyl-phosphine oxide)holmium(III). | 2010 May 12 |
|
| Investigation of Lewis acid versus Lewis base catalysis in asymmetric cyanohydrin synthesis. | 2010 Oct 4 |
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
Fri Dec 15 19:40:55 UTC 2023
by
admin
on
Fri Dec 15 19:40:55 UTC 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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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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791-28-6
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36601
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DTXSID2022121
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