Tetradecyltrimethylammonium bromide

Synthesis

400 kg of tetradecyldimethyl tertiary amine was weighed and placed in a 1000 L enamel-lined reactor. A mixture of 263 kg of hydrobromic acid, 125 kg of methanol, and 0.4 kg of the ionic liquid 1-ethyl-3-methylimidazolium hydrobromide was pumped in at a flow rate of 160 kg/h. The reaction was carried out under stirring at 50 °C for 3 hours under a nitrogen atmosphere and normal pressure. The reaction product was vacuum dried (drying temperature controlled at 80 °C) and then added to a 1000 L high-pressure reactor. After purging the reactor three times with nitrogen, a mixture of 168 kg of dimethyl carbonate and 80 kg of methanol was pumped in at a flow rate of 20 kg/h and the reactor was sealed for reaction at 175 °C and 1.7 MPa under stirring for 12 hours. After vacuum drying (drying temperature controlled at 80 °C), approximately 553 kg of Tetradecyltrimethylammonium bromide was obtained, with a yield of 99.1% and a purity of 99.1%.

Physical properties

Cetrimide is a white fine powder crystal with a melting point of 245°C to 250°C. A rough estimate of its density is 1.1328. It is soluble in water with a solubility of 20 g/100 mL.

Description

MiTMAB (1119-97-7) is a dynamin I/II inhibitor targeting the dynamin-phospholipid interaction and inhibiting dynamin GTPase activity with a Ki=940nM.1 Rapidly and reversibly inhibits multiple forms of endocytosis with no acute cellular damage1. A useful pharmacological tool for studying dynamin-mediated trafficking events.2 Induces cytokinesis failure and apoptosis in human cancer cells.3 Induces cytoprotective autophagy in human Jurkat T cells.4

Uses

Disinfectant; deodorant; laboratory reagent.

Uses

Myristyltrimethylammonium has been used in a study to assess a surfactant-controlled synthetic method to obtain a nanophase of mesoporous ceria-zirconia solid solution containing cationic defects in the crystalline structure.It has also been used in a study to determine the low molecular weight of organic acids in soils and plants by capillary zone electrophoresis.

Definition

Myristyltrimethylammonium bromide is an organic molecular entity.

General Description

Myristyltrimethylammonium bromide is a cationic/zwitterionic type of surfactant.

Purification Methods

Crystallise the bromide from acetone or a mixture of Me2CO and >5% MeOH or Me2CO/EtOH. Wash it with diethyl ether and dry it in a vacuum oven at 60o. It is a cationic detergent. Its solubility is 1g/5g H2O. [Dearden & Wooley J Phys Chem 91 2404 1987, Shelton et al. J Am Chem Soc 68 754 1946, Beilstein 4 III 419, 4 IV 813.]

References

1) ANNIE QUAN. Myristyl trimethyl ammonium bromide and octadecyl trimethyl ammonium bromide are surface-active small molecule dynamin inhibitors that block endocytosis mediated by dynamin I or dynamin II.[J]. Molecular Pharmacology, 2007, 72 6: 1425-1439. DOI:10.1124/mol.107.034207.
2) SAMIR VYAS. Development and validation of a stability indicating method for the enantioselective estimation of omeprazole enantiomers in the enteric-coated formulations by high-performance liquid chromatography.[J]. Journal of Pharmacy and Bioallied Sciences, 2011, 3 2: 310-314. DOI:10.4103/0975-7406.80766.
3) SIMON DE BECO. Endocytosis is required for E-cadherin redistribution at mature adherens junctions.[J]. ACS Catalysis , 2009: 7010-7015. DOI:10.1073/pnas.0811253106.
4) YOON HEE KIM . Inhibition of autophagy enhances dynamin inhibitor-induced apoptosis via promoting Bak activation and mitochondrial damage in human Jurkat T cells[J]. Biochemical and biophysical research communications, 2016, 478 4: Pages 1609-1616. DOI:10.1016/j.bbrc.2016.08.165.