Trimethylamine oxide

Base Information

• Chemical Name: Trimethylamine oxide
• CAS No.: 1184-78-7
• Molecular Formula: C3H9NO
• Molecular Weight: 75.1106
• Hs Code.: 2921110090
• European Community (EC) Number: 214-675-6
• NSC Number: 408426
• UNII: FLD0K1SJ1A
• DSSTox Substance ID: DTXSID8049678
• Nikkaji Number: J7.304K
• Wikipedia: Trimethylamine_N-oxide
• Wikidata: Q419802
• Metabolomics Workbench ID: 37502
• Mol file: 1184-78-7.mol

Synonyms:TMAO;trimethylamine N-oxide;trimethylamine oxide;trimethylammonium oxide;trimethyloxamine

Chemical Property of Trimethylamine oxide

Chemical Property:

• Vapor Pressure: 23.5Pa at 20℃
• Melting Point: 220-222 °C(lit.)
• Refractive Index: 1.4698 (estimate)
• Boiling Point: 133.8°C (rough estimate)
• PKA: 4.65(at 25℃)
• PSA: 29.43000
• Density: 0.9301 (rough estimate)
• LogP: 0.21130
• Storage Temp.: Hygroscopic, Room Temperature, under inert atmosphere
• Solubility.: Chloroform, DMSO, Methanol (Slightly)
• Water Solubility.: 793g/L at 24.5℃
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 75.068413911
• Heavy Atom Count: 5
• Complexity: 28.4

Purity/Quality:

99% ^*data from raw suppliers

Trimethylamine N-oxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Amine Oxides
• Canonical SMILES: C[N+](C)(C)[O-]
• 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.
• 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.

Technology Process of Trimethylamine oxide

There total 15 articles about Trimethylamine oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

trimethylamine (75-50-3) → trimethylamine-N-oxide (1184-78-7)

Guidance literature:

With oxygen; In water; at 100 ℃; for 64h; under 10500.8 Torr;

DOI:10.1021/jo00209a049

Reference yield: 94.0%

trimethylamine-N-oxide dihydrate (62637-93-8) → trimethylamine-N-oxide (1184-78-7)

Guidance literature:

With N,N-dimethyl-formamide; distillation;

DOI:10.1016/S0040-4039(00)84884-4

Reference yield:

trimethylamine (75-50-3) → formaldehyd (50-00-0,30525-89-4,61233-19-0) + trimethylamine-N-oxide (1184-78-7)

Guidance literature:

With ozone; In water; Kinetics;

upstream raw materials:

trimethyl-amine oxide; hydriodide

dimethyl sulfate

trimethylamine

trimethylamine-N-oxide dihydrate

Downstream raw materials:

N,N-dimethyl acetamide

Triphenylphosphine oxide

phenol; compound with trimethylamine oxide

1-methyl-3-phenylpyrrolidine

Refernces

• 1、 Shimizu, Makiko,Koibuchi, Natsumi,Mizugaki, Ami,Hishinuma, Eiji,Saito, Sakae,Hiratsuka, Masahiro,Yamazaki, Hiroshi. "Genetic variants of flavin-containing monooxygenase 3 (FMO3) in Japanese subjects identified by phenotyping for trimethylaminuria and found in a database of genome resources". . . Retrieved 2021.
• 2、 Giguere,Chin. "". . p. 1214,1218. Retrieved 1961.
• 3、 Pohl, Radek,Potmischil, Francisc,Dracinsky, Martin,Vanek, Vaclav,Slavetinska, Lenka,Budesinsky, Milos. "13C GIAO DFT calculation as a tool for configuration prediction of N-O group in saturated heterocyclic N-oxides". . p. 415 - 423. Retrieved 2012.
• 4、 Soderquist, John A.,Anderson, Charles L.. "CRYSTALLINE ANHYDROUS TRIMETHYLAMINE N-OXIDE". . p. 3961 - 3962. Retrieved 1986.
• 5、 Chen, Michael J.,Linehan, John C.,Rathke, Jerome W.. "Autoxidation of Trimethylamine in Aqueous Solutions". . p. 3233 - 3236. Retrieved 1990.
• 6、 Bao, Liang-Liang,Liu, Zai-Qun. "Tetrahydropyrrolization of Resveratrol and Other Stilbenes Improves Inhibitory Effects on DNA Oxidation". . p. 1617 - 1625. Retrieved 2016/08/28.