95115-21-2

Upstream product

• 100-09-4 4-methoxybenzoic acid 
• 106-89-8 epichlorohydrin 
• 121-98-2 methyl 4-methoxybenzoate 
• 556-52-5 oxiranyl-methanol 
• 100-07-2 4-methoxy-benzoyl chloride 

Downstream Products

• 851768-18-8 2-O-(4-methoxybenzoyl)-1,3-bis-O-(trifluoroacetyl)glycerol 
• 100059-63-0 2-O-(4-methoxybenzoyl)glycerol 

Relevant academic research and scientific papers

Synthesis of new (arylcarbonyloxy)aminopropanol derivatives and the determination of their physico-chemical properties

Eight hydrochlorides of 3-{2-[(2/4-fluorophenoxy)-ethylamino]}-2- hydroxypropyl-4-alkoxybenzoates and four hydrochlorides of 3-tert-butylamino-2- hydroxypropyl-4-butoxybenzoates were prepared as potential antagonists of the β1-adrenergic receptor (beta-blockers). A multistep synthesis of these compounds is described as well as their detailed analytical characterization. The pharmacokinetic properties of these weak base compounds are significantly influenced by their acid-base dissociation constant, pK a. The knowledge of this value is crucial for new drug development. This paper is aimed at developing a methodology that utilizes pH-dependent 1H NMR spectroscopy for its routine analysis. The selected predicted physico-chemical parameters of the new (arylcarbonyloxy)aminopropanols (i.e., aryloxyaminopropanol derivatives) were compared with the model drugs esmolol and flestolol. [Figure not available: see fulltext.]

Bioactive (co)oligoesters with antioxidant properties-synthesis and structural characterization at the molecular level

A contemporary synthetic route, starting from the bioactive compound via the corresponding glycidyl ester and β-substituted β-lactone to (homo)- and (co)oligoesters with a bioactive moiety covalently linked as pendent groups along an oligomer backbone, was reported. The bioactive compounds were selected from antioxidants used in cosmetics. Two models of bioactive (homo)- and (co)oligoesters were synthesized via anionic ring-opening (co)oligomerization of p-methoxybenzoyloxymethylpropiolactone (p-AA-CH2-PL) initiated by p-anisic acid sodium salt. An analytical protocol was developed for a detailed structural characterization at the molecular level of these bioactive (co)oligoesters. The molecular level structure of the obtained bioactive (homo)- and (co)oligoesters was established by electrospray ionization tandem mass spectrometry (ESI-MS/MS) supported by 1H NMR analysis. Additionally, the results presented here are important for the analysis of designed biodegradable polymeric controlled-release systems of bioactive compounds with potential applications in cosmetology.

Quaternary Alkyl Ammonium Salt-Catalyzed Transformation of Glycidol to Glycidyl Esters by Transesterification of Methyl Esters

Catalytic transformation of glycidol while maintaining its epoxide moiety intact is challenging because the terminal epoxide that interacts with the hydroxyl group via a hydrogen bond is labile for the ring-opening reaction. We found that a quaternary alkyl ammonium salt catalyzes the selective transformation of glycidol to glycidyl esters by transesterification of methyl esters. The developed method can be applied to the synthesis of multiglycidyl esters, which are valuable epoxy resin monomers. Mechanistic studies revealed the formation of a binding complex of glycidol and quaternary alkyl ammonium salt in a nonpolar solvent and the generation of the alkoxide anion as a catalyst through the ring-opening reaction of the epoxide. Computational studies of the reaction mechanism indicated that the alkoxide anion derived from glycidol tends to abstract the proton of another glycidol rather than work as a nucleophile, initiating the catalytic transesterification. Payne rearrangement of the deprotonated glycidol, which produces a destabilized base that promotes nonselective reactions, is energetically unfavorable due to the double hydrogen bond between the anion and diol. The minimal interaction between the quaternary alkyl ammonium cation and the epoxide moiety inhibited the random ring-opening pathway leading to polymerization.

Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl- and 1,3-symmetrical triacylglycerols

A trifluoroacetic anhydride-catalyzed opening of the oxirane system of glycidyl esters with a simultaneous migration of the acyl group provides a new, efficient entry to either 2-monoacylglycerols (2-MAG) or 1,3-symmetrical triglycerides (1,3-STG) as potential prodrug frameworks.

MECHANISM OF THE REACTION OF GLYCIDYL ESTERS WITH CARBOXYLIC ACIDS

The kinetics of the reactions of 1-phenoxy-2,3-epoxypropane and 2,3-epoxypropylbenzoate with carboxylic acids were investigated.A new reaction mechanism is proposed to explain the anomalously high reactivity of the glycidyl esters.The mechanism involves protonation of the oxygen of the carbonyl group in the ester followed by intramolecular electrophilic attack on the oxirane oxygen by the carbonyl carbon atom, accompanied by opening of the epoxide ring and transfer of the acyl fragment in the glycidyl ester molecule.