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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
Structure of TRIPHENYLPHOSPHINE OXIDE

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

HIDE SMILES / InChI

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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9NZQ8
Gene ID: 29850.0
Gene Symbol: TRPM5
Target Organism: Homo sapiens (Human)
12.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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
An unexpected co-crystal with a variable degree of order: 1:1 rac-1,2-cyclohexanediol/triphenylphosphine oxide.
2007 Dec
Bis(acetyl-acetonato)oxido(triphenyl-phosphine oxide)vanadium(IV).
2007 Dec 12
Identification of estrogenic compounds emitted from the combustion of computer printed circuit boards in electronic waste.
2007 Dec 15
Bis(2-benzoyl-1-phenyl-ethenolato-κO,O')(ethanol-κO)dioxidouranium(VI).
2007 Dec 18
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
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
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
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
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
Triphenylphosphine oxide is a potent and selective inhibitor of the transient receptor potential melastatin-5 ion channel.
2010 Dec
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
[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
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
The reaction chemistry of plutonyl(VI) chloride complexes with triphenyl phosphineoxide and triphenyl phosphinimine.
2010 Oct 18
Investigation of Lewis acid versus Lewis base catalysis in asymmetric cyanohydrin synthesis.
2010 Oct 4
Mass spectrometric characterization of metal triflates and triflimides (Lewis superacid catalysts) by electrospray ionization and tandem mass spectrometry.
2010 Sep 15
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
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 Fri Dec 15 19:40:55 GMT 2023
Edited
by admin
on Fri Dec 15 19:40:55 GMT 2023
Record UNII
Z69161FKI3
Record Status Validated (UNII)
Record Version
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Name Type Language
TRIPHENYLPHOSPHINE OXIDE
Systematic Name English
NSC-398
Code English
ORLISTAT RELATED COMPOUND C [USP-RS]
Common Name English
TRIPHENYLPHOSPHINE MONOXIDE
Systematic Name English
ALPROSTADIL IMPURITY K [EP IMPURITY]
Common Name English
ORLISTAT RELATED COMPOUND C [USP IMPURITY]
Common Name English
TRIPHENYL PHOSPHORUS OXIDE
Systematic Name English
PHOSPHINE OXIDE, TRIPHENYL-
Systematic Name English
Code System Code Type Description
PUBCHEM
13097
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
ECHA (EC/EINECS)
212-338-8
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
NSC
398
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
WIKIPEDIA
TRIPHENYLPHOSPHINE OXIDE
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
RS_ITEM_NUM
1478833
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
FDA UNII
Z69161FKI3
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
CAS
791-28-6
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
CHEBI
36601
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
EPA CompTox
DTXSID2022121
Created by admin on Fri Dec 15 19:40:56 GMT 2023 , Edited by admin on Fri Dec 15 19:40:56 GMT 2023
PRIMARY
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