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Trimethylamine N-oxide

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Trimethylamine N-oxide Basic information
Product Name:Trimethylamine N-oxide
Synonyms:n,n-dimethyl-methanaminn-oxide;Triox;TRIMETHYLAMINE N-OXIDE;TRIMETHYLAMINE OXIDE HYDROCHLORIDE;TRIMETHYLAMINE N-OXIDE HYDROCHLORIDE;trimethyl-oxido-ammonium;TRIMETHYLAMINOXIDE;Trimethylamine N-oxide,98%
CAS:1184-78-7
MF:C3H9NO
MW:75.11
EINECS:214-675-6
Product Categories:Oxidation;Synthetic Organic Chemistry
Mol File:1184-78-7.mol
Trimethylamine N-oxide Structure
Trimethylamine N-oxide Chemical Properties
Melting point 220-222 °C (lit.)
Boiling point 133.8°C (rough estimate)
density 0.9301 (rough estimate)
vapor pressure 23.5Pa at 20℃
refractive index 1.4698 (estimate)
FEMA 4245 | TRIMETHYLAMINE OXIDE
storage temp. Hygroscopic, Room Temperature, under inert atmosphere
solubility Chloroform, DMSO, Methanol (Slightly)
pka4.65(at 25℃)
form Solid
color Pale Yellow
Odorodorless
Water Solubility 793g/L at 24.5℃
JECFA Number1614
Merck 14,9711
Stability:Hygroscopic
InChI1S/C3H9NO/c1-4(2,3)5/h1-3H3
InChIKeyUYPYRKYUKCHHIB-UHFFFAOYSA-N
SMILESC[N+](C)(C)[O-]
LogP-2.79
EPA Substance Registry SystemMethanamine, N,N-dimethyl-, N-oxide (1184-78-7)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39
WGK Germany 3
TSCA TSCA listed
HS Code 2904.20.5000
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Inhalation
Acute Tox. 4 Oral
MSDS Information
ProviderLanguage
SigmaAldrich English
Trimethylamine N-oxide Usage And Synthesis
DescriptionTrimethylamine N-oxide (TMAO) is a metabolite of choline, phosphatidylcholine, and L-carnitine . It is formed by gut microbiota-mediated metabolism of choline, phosphatidylcholine, and L-carnitine to TMA followed by oxidation of TMA by flavin-containing monooxygenase 3 (FMO3) in the liver. Dietary administration of TMAO (0.12% w/w) increases renal tubulointerstitial fibrosis, collagen deposition, and Smad3 phosphorylation in mice and increases aortic lesion area in atherosclerosis-prone ApoE-/- mice. Plasma levels of TMAO are elevated in patients with chronic kidney disease and decreased in patients with active, compared with inactive, ulcerative colitis. Elevated plasma levels of TMAO are associated with increased risk of cardiovascular disease.
Chemical PropertiesColorless to yellow solid; odorless.
Chemical PropertiesWhite crystalline powder
UsesTrimethylamineN-oxide can be used:
  • As a demetallationand decarbonylationreagent for organometallic compounds.
  • To prepare azomethine ylide by reaction with lithium di-isopropylamide. This, in turn, may be reacted with simple alkenes to obtain corresponding pyrrolidines.
  • To mediate the conversion of thiols to disulfides.
DefinitionChEBI: An N-oxide derived from triethylamine.
General DescriptionTrimethylamineN-oxide is an organic compound that belongs to the class of amine oxides. It is generally found in the tissues of marine organisms, wherein it helps protect them from harsh conditions like salinity, hydrostatic pressure, temperature, and high urea.
Flammability and ExplosibilityNot classified
reaction suitabilityreagent type: oxidant
Trimethylamine N-oxide Preparation Products And Raw materials
Raw materialsToluene-->Hydrogen peroxide-->Trimethylamine
Preparation ProductsN,N'-Dimethylpiperazine-->2-Dimethylaminomethylphenol (contains phenol)-->(1-methylpyrrolidin-3-yl)methanol
Tag:Trimethylamine N-oxide(1184-78-7) Related Product Information
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