Trimethylamine N-oxide
Synonym(s):TMANO
- CAS NO.:1184-78-7
- Empirical Formula: C3H9NO
- Molecular Weight: 75.11
- MDL number: MFCD00082441
- EINECS: 214-675-6
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-17 21:30:02
What is Trimethylamine N-oxide?
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.
The Uses of Trimethylamine N-oxide
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.
What are the applications of Application
Trimethylamine N-oxide is a mediator of thiol-sulfide conversion
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
Properties of Trimethylamine N-oxide
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) |
form | Solid |
pka | 4.65(at 25℃) |
color | Pale Yellow |
Odor | odorless |
Water Solubility | 793g/L at 24.5℃ |
Merck | 14,9711 |
JECFA Number | 1614 |
Stability: | Hygroscopic |
EPA Substance Registry System | Methanamine, N,N-dimethyl-, N-oxide (1184-78-7) |
Safety information for Trimethylamine N-oxide
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P271:Use only outdoors or in a well-ventilated area. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
Computed Descriptors for Trimethylamine N-oxide
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