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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
Cosmetics Ingredients Functions
FRAGRANCE
HUMECTANT
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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