4276-74-8

Upstream product

• 150-76-5 4-methoxy-phenol 
• 92818-05-8 2-(4'-methoxyphenoxy)propanoic acid chloride 
• 13794-15-5 2-(4-methoxyphenoxy)propanoic acid 

Downstream Products

• 105118-15-8 (S)-2-(4-hydroxyphenoxy)propionic acid 

Relevant academic research and scientific papers

HPLC separation of 2-aryloxycarboxylic acid enantiomers on chiral stationary phases

The possibility for separating enantiomers of a number of practically significant 2-aryloxycarboxylic acids was studied by normal- and reversed-phase HPLC on popular chiral stationary phases. The best separation parameters were achieved on the chiral phases with the polysaccharide base Chiralcel OD-H and Chiralpack AD under the normal-phase HPLC conditions. The (S)- and (R)-enantiomers of 2-(1-naphthyloxy)- and 2-(2-iodophenoxy)propionic acids with enantiomeric excess ee >99% were isolated using preparative chiral HPLC.

Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor

Lactisole, an inhibitor of the human sweet taste receptor, has a 2-phenoxypropionic acid skeleton and has been shown to interact with the transmembrane domain of the T1R3 subunit (T1R3-TMD) of the receptor. Another inhibitor, 2,4-DP, which shares the same molecular skeleton as lactisole, was confirmed to be approximately 10-fold more potent in its inhibitory activity than lactisole; however the structural basis of their inhibitory mechanisms against the receptor remains to be elucidated. Crystal structures of the TMD of metabotropic glutamate receptors, which along with T1Rs are categorized as class C G-protein coupled receptors, have recently been reported and made it possible to create an accurate structural model for T1R3-TMD. In this study, the detailed structural mechanism underlying sweet taste inhibition was characterized by comparing the action of lactisole on T1R3-TMD with that of 2,4-DP. We first performed a series of experiments using cultured cells expressing the sweet taste receptor with mutations and examined the interactions with these inhibitors. Based on the results, we next performed docking simulations and then applied molecular dynamics-based energy minimization. Our analyses clearly revealed that the (S)-isomers of both lactisole and 2,4-DP, interacted with the same seven residues in T1R3-TMD and that the inhibitory potencies of those inhibitors were mainly due to stabilizing interactions mediated via their carboxyl groups in the vertical dimension of the ligand pocket of T1R3-TMD. In addition, 2,4-DP engaged in a hydrophobic interaction mediated by its o-Cl group, and this interaction may be chiefly responsible for the higher inhibitory potency of 2,4-DP.

Mutual Kinetic Resolution of Racemic 3,4-Dihydro-3-methyl-2H-[1,4]benzoxazines with Acyl Chlorides of Racemic O-Phenyllactic Acids and DFT Modelling of Transition States

The effect of the electronic nature of the para substituent on the aromatic ring of 2-aryloxypropionyl chlorides on the stereochemical outcome of the acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzoxazine and its 7,8-difluoro-containing analogue has been studied. The geometries of the diastereoisomeric transition states and the corresponding Gibbs free enthalpies of activation were determined through DFT calculations at the COSMO-CH2Cl2-B3LYP-D3-gCP/def2-TZVP (or def2-SVP)//B3LYP-D3-gCP/def2-SVP level of theory. It has been found that a low-cost quantum chemical calculation at a chosen level of theory describes well the quantitative dependence of the selectivity of acylation on the structures of the reagents. The obtained results indicate that aromatic interactions between the reagents play a significant role in the process of stereodifferentiation, ensuring high selectivity of the acylation of benzoxazines with 2-aryloxyacyl chlorides.

A great improvement of the enantioselectivity of lipase-catalyzed hydrolysis and esterification using co-solvents as an additive

Addition of co-solvents such as tetrahydrofuran resulted in a great improvement of the enantioselectivity of lipase-catalyzed hydrolysis of butyl 2-(4-substituted phenoxy)propanoates in an aqueous buffer solution. On the other hand, lipase lyophilized from an aqueous solution containing the co-solvents catalyzed highly enantioselective esterification of 2-(4-substituted phenoxy)propionic acids, 2-(4-isobutylphenyl)propionic acid (ibuprofen), and 2-(6-methoxy-2-naph-thyl)propionic acid (naproxen) in an organic solvent. An increase in the E value up to two orders of magnitude was observed for some substrates. The origin of the enantioselectivity enhancement caused by the co-solvent addition was mainly attributed to a significant deceleration in the initial reaction rate for the incorrectly binding enantiomer, as compared with that for the correctly binding enantiomer. From the results of FT-1R, CD, and ESR spectra, the co-solvent addition was also found to bring about a partial destruction of the tertiary structure of lipase.

Metal ions dramatically enhance the enantioselectivity for lipase-catalysed reactions in organic solvents

We propose a simple and a powerful method to enhance the enantioselectivity for lipase-catalysed transformations in organic solvents by an addition of metal ion-containing water to the reaction mixture. In this paper, various metal ions such as LiCl or MgCl2 are tested to improve the enantioselectivity for the model reactions. The enantioselectivities obtained are dramatically enhanced, the E values of which are about 100-fold as compared with the ordinary conditions without a metal ion, for example, E = 200 by addition of LiCl. Furthermore, lowering the reaction temperature led to an almost perfect enantioselectivity of lipase in the presence of a metal ion, for example, E = 1300 by addition of LiCl. Also, a mechanism for the drastic enhancement by metal ions is discussed briefly on the basis of the EPR spectroscopic study and the initial rate for each enantiomer of the substrate. The Royal Society of Chemistry 2006.

Process for the preparation of optically active 2-(4-methoxyphenoxy) propionic acid

A process for the preparation of optically active 2-(4-methoxyphenoxy)propionic acid of at least 75 percent enantiomeric excess of the desired optical isomer comprised of contacting 2-chloropropionic acid or a lower alkyl ester or an alkali metal salt thereof, having an optical purity greater than 85 percent of the opposite configuration, with from 3 to 10 molar equivalents of 4-methoxyphenol in an aqueous base.