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78-30-8 | Tri-o-tolyl phosphate
CAS No: 78-30-8 Catalog No: AG003V56 MDL No:MFCD00041906
Product Description
Catalog Number:
AG003V56
Chemical Name:
Tri-o-tolyl phosphate
CAS Number:
78-30-8
Molecular Formula:
C21H21O4P
Molecular Weight:
368.3628
MDL Number:
MFCD00041906
IUPAC Name:
tris(2-methylphenyl) phosphate
InChI:
InChI=1S/C21H21O4P/c1-16-10-4-7-13-19(16)23-26(22,24-20-14-8-5-11-17(20)2)25-21-15-9-6-12-18(21)3/h4-15H,1-3H3
InChI Key:
YSMRWXYRXBRSND-UHFFFAOYSA-N
SMILES:
Cc1ccccc1OP(=O)(Oc1ccccc1C)Oc1ccccc1C
EC Number:
201-103-5
UNII:
X8II18JD0A
NSC Number:
438
RTECS Number:
TD0350000
UN Number:
2574
Properties
Complexity:
416
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
368.118g/mol
Formal Charge:
0
Heavy Atom Count:
26
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
368.369g/mol
Monoisotopic Mass:
368.118g/mol
Rotatable Bond Count:
6
Topological Polar Surface Area:
44.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.1
Literature
| Title | Journal |
|---|---|
| Neutrophil depletion protects against zomepirac-induced acute kidney injury in mice. | Chemico-biological interactions 20180105 |
| Involvement of oxidative stress in tri-ortho-cresyl phosphate-induced liver injury in male mice. | Human & experimental toxicology 20161001 |
| Organophosphate Flame Retardants Act as Endocrine-Disrupting Chemicals in MA-10 Mouse Tumor Leydig Cells. | Toxicological sciences : an official journal of the Society of Toxicology 20160401 |
| Tri-ortho-cresyl phosphate induces autophagy of rat spermatogonial stem cells. | Reproduction (Cambridge, England) 20150201 |
| Identification of differentially expressed proteins related to organophosphorus-induced delayed neuropathy in the brains of hens. | Journal of applied toxicology : JAT 20141201 |
| Impairment of glutamate signaling in mouse central nervous system neurons in vitro by tri-ortho-cresyl phosphate at noncytotoxic concentrations. | Toxicological sciences : an official journal of the Society of Toxicology 20141101 |
| Organophosphorus flame retardants inhibit specific liver carboxylesterases and cause serum hypertriglyceridemia. | ACS chemical biology 20140516 |
| Induction of autophagy by TOCP in differentiated human neuroblastoma cells lead to degradation of cytoskeletal components and inhibition of neurite outgrowth. | Toxicology 20130809 |
| Identifying safer anti-wear triaryl phosphate additives for jet engine lubricants. | Chemico-biological interactions 20130325 |
| Inhibition pathways of the potent organophosphate CBDP with cholinesterases revealed by X-ray crystallographic snapshots and mass spectrometry. | Chemical research in toxicology 20130218 |
| Biochemical, histopathological and clinical evaluation of delayed effects caused by methamidophos isoforms and TOCP in hens: ameliorative effects using control of calcium homeostasis. | Toxicology 20121208 |
| Metabolic activation by human arylacetamide deacetylase, CYP2E1, and CYP1A2 causes phenacetin-induced methemoglobinemia. | Biochemical pharmacology 20121101 |
| Cresyl saligenin phosphate, an organophosphorus toxicant, makes covalent adducts with histidine, lysine, and tyrosine residues of human serum albumin. | Chemical research in toxicology 20120820 |
| Sensitivity of 2H NMR spectroscopy to motional models: proteins and highly viscous liquids as examples. | The Journal of chemical physics 20120628 |
| Endocrine disruption potentials of organophosphate flame retardants and related mechanisms in H295R and MVLN cell lines and in zebrafish. | Aquatic toxicology (Amsterdam, Netherlands) 20120615 |
| Involvement of neuropathy target esterase in tri-ortho-cresyl phosphate-induced testicular spermatogenesis failure and growth inhibition of spermatogonial stem cells in mice. | Toxicology letters 20120520 |
| Changes in beclin-1 and micro-calpain expression in tri-ortho-cresyl phosphate-induced delayed neuropathy. | Toxicology letters 20120505 |
| Acute airway irritation of methyl formate in mice. | Archives of toxicology 20120201 |
| Reduction of retrograde axonal transport associated-proteins motor proteins, dynein and dynactin in the spinal cord and cerebral cortex of hens by tri-ortho-cresyl phosphate (TOCP). | Neurochemistry international 20120101 |
| Analgesic activity and safety of ash of silver used in Indian system of medicine in mice: a reverse pharmacological study. | Indian journal of pharmacology 20120101 |
| Voltammetric determination of the herbicide Linuron using a tricresyl phosphate-based carbon paste electrode. | Sensors (Basel, Switzerland) 20120101 |
| [The differential expression of Stathmin in the spinal cord tissue of hens exposed to tri-o-cresyl phosphate]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20111201 |
| Exposure to tri-o-cresyl phosphate detected in jet airplane passengers. | Toxicology and applied pharmacology 20111101 |
| Induction of plasma acetylcholinesterase activity in mice challenged with organophosphorus poisons. | Toxicology and applied pharmacology 20110901 |
| Changes of mitochondrial ultrastructures and function in central nervous tissue of hens treated with tri-ortho-cresyl phosphate (TOCP). | Human & experimental toxicology 20110801 |
| Determination of tricresyl phosphate air contamination in aircraft. | The Annals of occupational hygiene 20110801 |
| [Simultaneous determination of six organophosphorous flame retardants in textiles by gas chromatography-tandem mass spectrometry combined with microwave assisted extraction]. | Se pu = Chinese journal of chromatography 20110801 |
| Reaction of cresyl saligenin phosphate, the organophosphorus agent implicated in aerotoxic syndrome, with human cholinesterases: mechanistic studies employing kinetics, mass spectrometry, and X-ray structure analysis. | Chemical research in toxicology 20110620 |
| Organophosphates in aircraft cabin and cockpit air--method development and measurements of contaminants. | Journal of environmental monitoring : JEM 20110501 |
| [Screening the proteins of organophosphoms ester-induced delayed neurotoxicity in the cerebral tissue of hens exposed to tri-ortho-cresyl phosphate]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20110501 |
| Methyl methacrylate and respiratory sensitization: a critical review. | Critical reviews in toxicology 20110301 |
| Serum creatine phosphokinase: a probable marker of severity in organophosphorus poisoning. | Toxicology international 20110101 |
| Exposure to airborne organophosphates originating from hydraulic and turbine oils among aviation technicians and loaders. | Journal of environmental monitoring : JEM 20101201 |
| Vacuoles in dorsal root Ganglia neurons: some questions. | Toxicologic pathology 20101001 |
| Development of diagnostics in the search for an explanation of aerotoxic syndrome. | Analytical biochemistry 20100901 |
| Vacuolation of sensory ganglion neuron cytoplasm in rats with long-term exposure to organophosphates. | Toxicologic pathology 20100601 |
| [Effect of phenylmethylsulfonyl fluoride pretreated on neurofilament subunits in spinal cords of hens administrated with tri-o-cresyl phosphate]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20100401 |
| House dust concentrations of organophosphate flame retardants in relation to hormone levels and semen quality parameters. | Environmental health perspectives 20100301 |
| Adulterated cocaine and lessons learned from the Jake walk blues. | Journal of medical toxicology : official journal of the American College of Medical Toxicology 20100301 |
| Organophosphorus-induced delayed neuropathy: a simple and efficient therapeutic strategy. | Toxicology letters 20100201 |
| Identification and characterization of biomarkers of organophosphorus exposures in humans. | Advances in experimental medicine and biology 20100101 |
| Neuropathological studies of chickens following exposure to chlorpyrifos. | Toxicology international 20100101 |
| Thirteen-year follow-up of patients with tri-ortho-cresyl phosphate poisoning in northern suburbs of Xi'an in China. | Neurotoxicology 20091101 |
| Phenylmethylsulfonyl fluoride protects against the degradation of neurofilaments in tri-ortho-cresyl phosphate (TOCP) induced delayed neuropathy. | Toxicology 20090821 |
| The homeostasis of phosphatidylcholine and lysophosphatidylcholine in nervous tissues of mice was not disrupted after administration of tri-o-cresyl phosphate. | Toxicological sciences : an official journal of the Society of Toxicology 20090601 |
| Amplify, amplify: shotgun proteomics boosts the signal for biomarker discovery. | Environmental health perspectives 20090501 |
| Neurofilaments degradation as an early molecular event in tri-ortho-cresyl phosphate (TOCP) induced delayed neuropathy. | Toxicology 20090428 |
| Respiratory and dermal exposure to organophosphorus flame retardants and tetrabromobisphenol A at five work environments. | Environmental science & technology 20090201 |
| Design of a small personal air monitor and its application in aircraft. | The Science of the total environment 20090115 |
| Effect of inhibition of neuropathy target esterase in mouse nervous tissues in vitro on phosphatidylcholine and lysophosphatidylcholine homeostasis. | International journal of toxicology 20090101 |
| Allergic contact dermatitis from tricresyl phosphate. | Dermatitis : contact, atopic, occupational, drug 20090101 |
| Toxic neuropathies. | Neurology India 20090101 |
| Radial neuropathy due to occupational lead exposure: Phenotypic and electrophysiological characteristics of five patients. | Annals of Indian Academy of Neurology 20090101 |
| The homeostasis of phosphatidylcholine and lysophosphatidylcholine was not disrupted during tri-o-cresyl phosphate-induced delayed neurotoxicity in hens. | Toxicology 20081030 |
| Worms and germs, drink and dementia: US health, society, and policy in the early 20th century. | Preventing chronic disease 20081001 |
| Growth inhibition and induction of G(1) phase cell cycle arrest in neuroblastoma SH-SY5Y cell by tri-ortho-cresyl phosphate. | Toxicology letters 20080901 |
| Determination of ortho-cresyl phosphate isomers of tricresyl phosphate used in aircraft turbine engine oils by gas chromatography and mass spectrometry. | Journal of chromatography. A 20080725 |
| Shear small-angle light scattering studies of shear-induced concentration fluctuations and steady state viscoelastic properties. | The Journal of chemical physics 20080428 |
| Effects of calcium gluconate and PMSF in the treatment of acute intoxication of chicken by TOCP. | Human & experimental toxicology 20080301 |
| Antibodies to neural proteins in organophosphorus-induced delayed neuropathy (OPIDN) and its amelioration. | Neurotoxicology and teratology 20080101 |
| An Effective On-line Polymer Characterization Technique by Using SALS Image Processing Software and Wavelet Analysis. | Journal of automated methods & management in chemistry 20080101 |
| In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. | Drug metabolism and disposition: the biological fate of chemicals 20071001 |
| Time-dependent changes of lipid peroxidation and antioxidative status in nerve tissues of hens treated with tri-ortho-cresyl phosphate (TOCP). | Toxicology 20070924 |
| Axonal degeneration and neuropathy target esterase. | Arhiv za higijenu rada i toksikologiju 20070901 |
| Multiscale analysis of liquid lubrication trends from industrial machines to micro-electrical-mechanical systems. | Langmuir : the ACS journal of surfaces and colloids 20070828 |
| Determination of airborne trialkyl and triaryl organophosphates originating from hydraulic fluids by gas chromatography-mass spectrometry. Development of methodology for combined aerosol and vapor sampling. | Journal of chromatography. A 20070817 |
| Verapamil abolished the enhancement of protein phosphorylation of brainstem mitochondria and synaptosomes from the hens dosed with tri-o-cresyl phosphate. | Environmental toxicology and pharmacology 20070701 |
| Modified carbon paste sensor for cetyltrimethylammonium ion based on its ion-associate with tetrachloropalladate(II). | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20070501 |
| [Tri-ortho-cresyl phosphate induced oligodendrocyte vacuolation and process degeneration in cultured hen oligodendrocytes]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20070501 |
| [Determination of three organophosphorous flame retardants in textiles by gas chromatography]. | Se pu = Chinese journal of chromatography 20070501 |
| STM, QCM, and the windshield wiper effect: a joint theoretical-experimental study of adsorbate mobility and lubrication at high sliding rates. | Langmuir : the ACS journal of surfaces and colloids 20061107 |
| Triorthocresyl phosphate-induced neuronal losses in lumbar spinal cord of hens--an immunohistochemistry and ultrastructure study. | The International journal of neuroscience 20061101 |
| Effect of tri-o-cresyl phosphate on cytoskeleton in human neuroblastoma SK-N-SH cell. | Molecular and cellular biochemistry 20061001 |
| Aberrant activation of CDK5 is involved in the pathogenesis of OPIDN. | Journal of neurochemistry 20061001 |
| Diffusion on a self-assembled monolayer: molecular modeling of a bound + mobile lubricant. | The journal of physical chemistry. B 20060810 |
| Expression changes of neurofilament subunits in the central nervous system of hens treated with tri-ortho-cresyl phosphate (TOCP). | Toxicology 20060601 |
| Workgroup report: Implementing a national occupational reproductive research agenda--decade one and beyond. | Environmental health perspectives 20060301 |
| Chemically modified carbon paste electrode for the potentiometric flow injection analysis of piribedil in pharmaceutical preparation and urine. | Journal of pharmaceutical and biomedical analysis 20050715 |
| [Tricresyl phosphate residue in garland chrysanthemum and its origin]. | Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20050401 |
| Neuropathological studies of rats following multiple exposure to tri-ortho-tolyl phosphate, chlorpyrifos and stress. | Toxicologic pathology 20050101 |
| Organophosphate-induced delayed polyneuropathy. | Toxicological reviews 20050101 |
| Organophosphate flame retardants and plasticizers in indoor air. | Chemosphere 20041101 |
| Mechanism of differential inhibition of hepatic and pancreatic fatty acid ethyl ester synthase by inhibitors of serine-esterases: in vitro and cell culture studies. | Toxicology and applied pharmacology 20041001 |
| Tri-ortho-cresyl phosphate (TOCP) decreases the levels of cytoskeletal proteins in hen sciatic nerve. | Toxicology letters 20040910 |
| Patch test results with the metalworking fluid series of the German Contact Dermatitis Research Group (DKG). | Contact dermatitis 20040901 |
| Effects of prednisolone and complex of vitamin B1, B2, B6 and B12 on organophosphorus compound-induced delayed neurotoxicity. | Journal of occupational health 20040901 |
| Modulation of fatty acid methyl esters in rats pretreated with tri-o-tolyl phosphate. | Journal of toxicology and environmental health. Part A 20040409 |
| Neurologic and immunologic effects of exposure to corticosterone, chlorpyrifos, and multiple doses of tri-ortho-tolyl phosphate over a 28-day period in rats. | Journal of toxicology and environmental health. Part A 20040312 |
| [Spinal cord neuronal apoptosis induced by triorthocresyl phosphate poisoning in hens]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20040201 |
| An acute toxic neuropathy caused by organo-phosphate poisoning in hens. | Bratislavske lekarske listy 20040101 |
| The effect of Calcicol as calcium tonic on delayed neurotoxicity induced by organophosphorus compounds. | Toxicology letters 20030605 |
| [Effects of organophosphates on cell proliferation and 45Ca uptake of neuroblastoma SH-SY5Y cells]. | Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases 20030601 |
| [Determination method of tricresyl phosphate in polyvinyl chloride]. | Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan 20030201 |
| [The use of probit-method for an estimation of toxic effects of combined toxicants at low concentration levels]. | Radiatsionnaia biologiia, radioecologiia 20030101 |
| Organophosphate induced delayed neuropathy in genetically dissimilar chickens: studies with tri-ortho-cresyl phosphate (TOCP) and trichlorfon. | Toxicology letters 20021215 |
| Preparation of refractive index matching polymer film alternative to oil for use in a portable surface-plasmon resonance phenomenon-based chemical sensor method. | Analytical and bioanalytical chemistry 20020701 |
| Degradation of organophosphoric esters in leachate from a sea-based solid waste disposal site. | Chemosphere 20020701 |
| Simple and rapid determination of iodide in table salt by stripping potentiometry at a carbon-paste electrode. | Analytical and bioanalytical chemistry 20020401 |
| Differential inhibition of hepatic, pancreatic, and plasma fatty acid ethyl ester synthase by tri-o-tolylphosphate in rats. | Toxicology and applied pharmacology 20020301 |
| Perspectives of carbon paste electrodes in stripping potentiometry. | Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20020301 |
| Organophosphorus compounds alter intracellular F-actin content in SH-SY5Y human neuroblastoma cells. | Neurotoxicology 20011201 |
| Inhibition of calcium-stimulated ATPase in the hen brain P2 synaptosomal fraction by organophosphorus esters: relevance to delayed neuropathy. | Journal of toxicology and environmental health. Part A 20010525 |
| The potential for toxic effects of chronic, low-dose exposure to organophosphates. | Toxicology letters 20010331 |
| Effects of neuropathic and non-neuropathic isomers of tricresyl phosphate and their microsomal activation on the production of axon-like processes by differentiating mouse N2a neuroblastoma cells. | Journal of neurochemistry 20010201 |
| Esterase inhibition in SH-SY5Y human neuroblastoma cells following exposure to organophosphorus compounds for 28 days. | In vitro & molecular toxicology 20010101 |
| Organophosphorus compound-induced apoptosis in SH-SY5Y human neuroblastoma cells. | Toxicology and applied pharmacology 20001015 |
| Brainstem axolemmal protein phosphorylation in vitro in hens dosed with di-1-butyl-2,2-dichlorovinyl phosphate. | Journal of toxicology and environmental health. Part A 19990226 |
| The contribution of oxidation and deacetylation to acetaminophen nephrotoxicity in female Sprague-Dawley rats. | Toxicology letters 19970919 |
| Comparison of the relative inhibition of acetylcholinesterase and neuropathy target esterase in rats and hens given cholinesterase inhibitors. | Fundamental and applied toxicology : official journal of the Society of Toxicology 19950101 |
| Evidence against deacetylation and for cytochrome P450-mediated activation in acetaminophen-induced nephrotoxicity in the CD-1 mouse. | Toxicology and applied pharmacology 19910101 |
| Histopathological assessment of triphenyl phosphite neurotoxicity in the hen. | Neurotoxicology 19880101 |
| Dose-related beneficial and adverse effects of dietary corticosterone on organophosphorus-induced delayed neuropathy in chickens. | Toxicology and applied pharmacology 19860401 |
| Lymphocyte and brain neurotoxic esterase: dose and time dependence of inhibition in the hen examined with three organophosphorus esters. | Toxicology and applied pharmacology 19860330 |
| Assessment of the delayed neurotoxic potential of isopropyl triphenylphosphate using a nontraditional testing strategy. | Journal of toxicology and environmental health 19840101 |
| The time course of protection from delayed neurotoxicity induced by tri-o-cresyl phosphate and O,O-diisopropyl phosphorofluoridate by phenyl methyl sulfonyl fluoride in chickens. | Toxicology letters 19830901 |
| Jamaica ginger paralysis. Forty-seven-year follow-up. | Archives of neurology 19780801 |
| [Prevention of experimental neuritis induced by nitrofurantoin and triorthocresylphosphate]. | Bollettino chimico farmaceutico 19770201 |
| The Jake Walk Blues. A toxicologic tragedy mirrored in American popular music. | Annals of internal medicine 19761201 |
| Cholinesterase levels in the nervous system in tri-ortho-cresyl phosphate poisoning. | British journal of pharmacology and chemotherapy 19521201 |
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