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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
  • TMAO
  • Trimethylamine oxide
  • trimethyloxamine
  • Triox
  • TRIMETHYLAMINE N-OXIDE
  • TRIMETHYLAMINE OXIDE HYDROCHLORIDE
  • TRIMETHYLAMINE N-OXIDE HYDROCHLORIDE
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
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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)
pka
4.65(at 25℃)
form 
Solid
color 
Pale Yellow
Odor
odorless
Water Solubility 
793g/L at 24.5℃
Merck 
14,9711
JECFA Number
1614
Stability:
Hygroscopic
LogP
-2.79
EPA Substance Registry System
Methanamine, N,N-dimethyl-, N-oxide (1184-78-7)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39
WGK Germany 
3
HS Code 
2904.20.5000

MSDS

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Trimethylamine N-oxide Usage And Synthesis

Description

Trimethylamine 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 Properties

White crystalline powder

Chemical Properties

Colorless to yellow solid; odorless.

Uses

Trimethylamine?N-oxide can be used:

  • As a demetallation?and decarbonylation?reagent 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.

Definition

ChEBI: An N-oxide derived from triethylamine.

General Description

Trimethylamine?N-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 Explosibility

Not classified

Trimethylamine N-oxide Preparation Products And Raw materials

Raw materials

Trimethylamine N-oxideSupplier

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