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Trimethylamine N-oxide dihydrate

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Trimethylamine N-oxide dihydrate Basic information

Product Name:
Trimethylamine N-oxide dihydrate
Synonyms:
  • methanamineoxide,n,n-dimethyl,dihydrate
  • n,n-dimethylmethanamineoxide,dihydrate
  • trimethylammoniumoxidhydrat
  • TMO
  • TRIMETHYLAMINE N-OXIDE DIHYDRATE
  • TRIMETHYLAMINE OXIDE DIHYDRATE
  • TMANO
  • TrimethylamineN-oxidedihydrate,98%
CAS:
62637-93-8
MF:
C3H13NO3
MW:
111.14
EINECS:
678-501-4
Product Categories:
  • Amines
  • Catalyst
  • Oxidation
  • Synthetic Organic Chemistry
  • bc0001
Mol File:
62637-93-8.mol
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Trimethylamine N-oxide dihydrate Chemical Properties

Melting point:
95-99 °C(lit.)
Flash point:
95 °C
storage temp. 
Sealed in dry,Room Temperature
solubility 
DMSO (Slightly), Methanol (Sparingly)
form 
Fine Crystalline Powder
color 
White to off-white
Water Solubility 
Soluble in water, ethanol, dimethyl sulfoxide and methanol. Sparingly soluble in hot chloroform. Insoluble in diethyl ether, benzene and hydrocarbon solvents.
Merck 
14,9711
BRN 
3612927
InChI
InChI=1S/C3H9NO.2H2O/c1-4(2,3)5;;/h1-3H3;2*1H2
InChIKey
PGFPZGKEDZGJQZ-UHFFFAOYSA-N
SMILES
[N+]([O-])(C)(C)C.O.O
CAS DataBase Reference
62637-93-8(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/38-20/21/22
Safety Statements 
26-36-37/39
WGK Germany 
2
RTECS 
YH2850000
4.10
TSCA 
Yes
HS Code 
29211990

MSDS

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Trimethylamine N-oxide dihydrate Usage And Synthesis

Chemical Properties

white crystalline powder

Uses

Trimethylamine N-Oxide Dihydrate is as an oxygen transfer agent used to promote heterometallic cluster catalyzing coordinative hydrogenation. Trimethylamine N-Oxide Dihydrate is also used as a catalyst in the preparation of thermally stable TiO2 nanorod incorporated polymers and semiconductor/metal nanocomposites.

Uses

Trimethylamine N-oxide dihydrate is used as an oxidizing agent in organic synthesis. It is also used to make quaternary ammonium compounds and a warning agent for flammable gas. Further, it acts as a flavoring agent or adjuvant. It serves as an oxidant for the catalytic osmium tetraoxide cis-hydroxylation of hindered olefins. In addition to this, it is used as a reactant for C-H bond cleavage and decarbonylating agent for solvent-free reactions.

Uses

Oxidizing reagent in organic synthesis.

General Description

Trimethylamine N-oxide (TMAO) is an amphiphilic osmolyte that can counteract the denaturing effects of urea, pressure, and ice and stabilize the proteins.

reaction suitability

reagent type: oxidant

in vivo

Trimethylamine N-oxide (TMAO) dihydrate contributes to cardiovascular diseases by promoting inflammatory responses. C57BL/6 mice are fed a normal diet, high-choline diet and/or 3-dimethyl-1-butanol (DMB) diet. The levels of Trimethylamine N-oxide dihydrate and choline are increased in choline-fed mice. Left ventricular hypertrophy, pulmonary congestion, and diastolic dysfunction are markedly exacerbated in heart failure with preserved ejection fraction (HFpEF) mice fed high-choline diets compared with mice fed the control diet. Myocardial fibrosis and inflammation were markedly increased in HFpEF mice fed high-choline diets compared with animals fed the control diet[1].
Trimethylamine N-oxide (dihydrate) can be used in animal modeling to construct models of cardiovascular and metabolic diseases[1].

Induction of cardiovascular and metabolic diseases
Background
Trimethylamine N-oxide (dihydrate) stimulated cardiac hypertrophy, as indicated by increased cell area of cardiomyocytes and expression of hypertrophic markers including atrial natriuretic peptide (ANP) and beta-myosin heavy chain (β-MHC). Additionally, Trimethylamine N-oxide (dihydrate) induced cardiac hypertrophy and cardiac fibrosis in SD rats[2].
Specific Mmodeling Methods
Rats: Wistar? male? weighing 200-250 g[1]
Administration: 100 μM and 1 mM? perfusion or incubation in TMAO-containing buffer solution? incubated for 1 h[1]
Mice: CD-1? male? weighing 25-30 g? 6-8 weeks of age[1]
Administration: 120 mg/kg? mixed with drinking water? a single dose or daily for 7 days[1]
Note
(1)Rat hearts were perfused, and aortic rings from each experimental animal were immersed in K+-H+ buffer solution with or without the addition of Trimethylamine N-oxide (dihydrate) (100 μM final concentration). After 1 h of perfusion or incubation, the tissue samples were washed to eliminate the residues of TMAO-containing buffer solution and further homogenized with water in an OMNI Bead Ruptor 24 at a w/v ratio of 1:10[1].
(2)All experimental animals were housed under standard conditions (21-23℃, 12-hour light/dark cycle, relative humidity 45-65%) with unlimited access to food (R70 diet) and water[1].
(3)The mice from the first experimental group received Isoproterenol (HY-B1670A) at a dose of 10 μg/mouse, but the animals from the second group received Isoproterenol (HY-B1670A) and Trimethylamine N-oxide (dihydrate) at doses of 10 μg/mouse and 120 mg/kg, respectively. After 30 min, the experimental animals were anesthetized with isoflurane once more to record the cardiac response to acute cardiac stress and the impact of Trimethylamine N-oxide (dihydrate) on the inotropic and chronotropic effects. For the next seven days, the mice in the second group received Trimethylamine N-oxide (dihydrate) together with drinking water at a dose of 120 mg/kg, while the animals from the first group received pure drinking water[1].
Modeling Indicators
Molecular changes: The addition of 100 μM Trimethylamine N-oxide (dihydrate) to the buffer solution increased the content of Trimethylamine N-oxide (dihydrate) in cardiac tissue by three and in the aortic rings by two points five times[1].
Pathology change: Trimethylamine N-oxide (dihydrate) had no influence on Isoproterenol (HY-B1670A)-induced increase on left ventricular ejection fraction, fractional shortening and heart rate[1].
Histological analysis: Promote myocardial hypertrophy, fibrosis, and inflammation in a model of cardiovascular disease (CVD)[3].
Correlated Product(s):Isoproterenol (HY-B1670A)
3,3-dimethyl-1-butanol (HY-W012977)

IC 50

Human Endogenous Metabolite; NLRP3; Microbial Metabolite

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