73159-12-3

Upstream product

• 66664-66-2 methoxytriethyleneglycol carboxylic acid ethyl ester 
• 112-35-6 triethylene glucol monomethyl ether 
• 79-08-3 bromoacetic acid 
• 16024-60-5 3,6,9,12-tetraoxatridecanoic acid 

Downstream Products

• 16024-60-5 3,6,9,12-tetraoxatridecanoic acid 
• 73159-14-5 1,2:5,6-di-O-isopropylidene-3-O-(3,6,9,12-tetraoxatridecanoyl)-α-D-glucofuranose 
• 73159-16-7 4,6-O-benzylidene-2,3-di-O-(3,6,9,12-tetraoxatridecanoyl)-α-D-glucupyranoside 
• 73159-15-6 1,2-O-isopropylidene-3,5,6-tri-O-(3,6,9,12-tetraoxatridecanoyl)-α-D-glucofuranose 
• 23783-42-8 tetraethylene glycol monomethyl ether 

Relevant academic research and scientific papers

Ionic liquids

Novel ionic liquids comprising polyethercarboxylates as anions, a process for preparing them and their use.

Alkali metal oligoether carboxylates - A new class of ionic liquids

A new group of ionic liquids (IL) based on small inorganic cations and oligoether carboxylate anions were synthesized. The physicochemical properties of the salts were also investigated, and possible reasons for the formation of ionic liquids with alkali metal ions were proposed. It was found that complexation of the alkali metal cations by their combined oligoether- carboxylate counter-ion was sufficient to generate room-temperature liquid salts. It was also found that the use of simple tri- and tetraalkylammonium instead of alkali metal ions could also yielded ionic liquids at ambient temperature that appear to display additional desirable properties such as low viscosity. The result also showed that the combination of the 2,5,8,1 l-tetraoxatridecan-13-oate (TOTO) anion with biological cations such as choline could also lead to the development of even greener ILs.

Poly(ethylene glycol)-based stable isotope labeling reagents for the quantitative analysis of low molecular weight metabolites by LC-MS

Stable isotope labeling (SIL) in combination with liquid chromatography-mass spectrometry is one of the most widely used quantitative analytical methods due to its sensitivity and ability to deal with extremely complex biological samples. However, SIL methods for metabolite analysis are still often limited in terms of multiplexing, the chromatographic properties of the derivatized analytes, or their ionization efficiency. Here we describe a new family of reagents for the SIL of primary amine-containing compounds based on pentafluorophenyl-activated esters of 13C-containing poly(ethylene glycol) chains (PEG) that addresses these shortcomings. A sequential buildup of the PEG chain allowed the introduction of various numbers of 13C atoms opening extended multiplexing possibilities. The PEG derivatives of rather hydrophilic molecules such as amino acids and glutathione were successfully retained on a standard C18 reversed-phase column, and their identification was facilitated based on m/z values and retention times using extracted ion chromatograms. The mass increase due to PEG derivatization moved low molecular weight metabolite signals out of the often noisy, low m/z region of the mass spectra, which resulted in enhanced overall sensitivity and selectivity. Furthermore, elution at increased retention times resulted in efficient electrospray ionization due to the higher acetonitrile content in the mobile phase. The method was successfully applied to the quantification of intracellular amino acids and glutathione in a cellular model of human lung epithelium exposed to cigarette smoke-induced oxidative stress. It was shown that the concentration of most amino acids increased upon exposure of A549 cells to gas-phase cigarette smoke with respect to air control and cigarette smoke extract and that free thiol-containing species (e.g., glutathione) decreased although disulfide bond formation was not increased. These labeling reagents should also prove useful for the labeling of peptides and other compounds containing primary amine functionalities.