1129-46-0

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(+)-2-Phenoxypropionic acid is used as an antimicrobial agent for its ability to inhibit the growth of bacteria, making it a potential candidate for medical applications in treating bacterial infections.
Used in Agrochemical Industry:
(R)-(+)-2-Phenoxypropionic acid is used as a key component in the production of herbicides and fungicides, contributing to the development of effective crop protection solutions.
Used in Chemical Industry:
(R)-(+)-2-Phenoxypropionic acid is utilized in the manufacturing of dyes and perfumes, playing a crucial role in the creation of various colorants and fragrances for different applications.

InChI:InChI=1/C9H10O3/c1-7(9(10)11)12-8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)/t7-/m1/s1

Upstream product

• 42412-84-0 ethyl 2-phenoxypropionate 
• 54656-96-1 (S)-1-(4-pyridyl)ethanol 
• 446878-78-0 2-Phenoxypropionsaeureanhydrid 
• 115880-50-7 (R)-2-phenoxypropanoic acid methyl ester 
• 940-31-8 2-phenoxypropionic acid 
• 57057-80-4 ethyl (S)-2-[[(4-methylphenyl)sulfonyl]oxy]propanoate 
• 108-95-2 phenol 
• 32644-15-8 (S)-2-bromopropanoic acid 
• 10009-70-8 R-(+)-2-bromopropionic acid 
• 62784-66-1 bis(1-naphthyl)methanol 
• 82419-33-8 (-)-7,8-difluoro-2,3-dihydro-3-methyl-4H-1,4-benzoxazine 
• 147851-69-2 (R)-2-phenoxypropionyl chloride 
• 74533-11-2 L-2-chloropropionic acid sodium salt 
• 223799-41-5 (S)-2-Phenoxy-N-((S)-1-phenyl-ethyl)-propionamide 

Downstream Products

• 32403-66-0 D-2-(2,4-dinitro-phenoxy)-propionic acid 
• 34378-72-8 6β-((R)-2-phenoxy-propionylamino)-penicillanic acid 
• 147851-69-2 (R)-2-phenoxypropionyl chloride 
• 91712-57-1 (P)-(-)-2,7,12-tris<((R)-2-phenoxypropanoyl)oxy>-10,15-dihydro-5H-tribenzocyclononene 
• 89255-52-7 (M)-(+)-2,7,12-tris<((R)-2-phenoxypropanoyl)oxy>-10,15-dihydro-5H-tribenzocyclononene 
• 184178-55-0 (S)-N-(1-phenylethyl)-(R)-2-phenoxypropionamide 
• 94050-90-5 (R)-2-(4-hydroxyphenoxy)propionic acid 
• 115880-50-7 (R)-2-phenoxypropanoic acid methyl ester 
• 189300-43-4 (R)-(+)-3-phenoxy-2-butanone 
• 664374-43-0 2-methyl-2-(1-phenoxyethyl)-1-oxaspiro[2,2]pentane 

Relevant academic research and scientific papers

Dimethyl sulfoxide as a co-solvent dramatically enhances the enantioselectivity in lipase-catalysed resolutions of 2-phenoxypropionic acyl derivatives

We recently reported that the enantioselectivity for subtilisin-catalysed hydrolysis of ethyl 2-(4-substituted phenoxy)-propionates in aqueous buffer is found to be dramatically enhanced by addition of dimethyl sulfoxide (DMSO). In our present work, as one of the useful methods for improving the enzyme's enantioselectivity, this approach using DMSO is tested for both hydrolysis and transesterification catalysed by various lipases. For instance, for Candida rugosa lipase-catalysed hydrolysis in aqueous buffer containing DMSO, the optimum additive conditions (50-65 vol% DMSO) markedly enhance the enantioselectivity toward the substrates used, as compared with that for no-additive conditions, in spite of a decrease in the enzymatic activity. On the other hand, for Pseudomonas cepacia lipase-catalysed hydrolysis, the addition of DMSO to the reaction medium enhances the enantioselectivity with an increase in the enzymatic activity. Also, the DMSO effect on the enantioselectivity can apply to the lipase-catalysed transesterification in organic solvent. A mechanism for the DMSO-induced enhancement of the lipase's enantioselectivity is briefly discussed on the basis of the values of the initial rates obtained for each enantiomer of the substrate used.

Improvement of catalytic activity of Candida rugosa lipase in the presence of calix[4]arene bearing iminodicarboxylic/phosphonic acid complexes modified iron oxide nanoparticles

In the present study, iron oxide magnetite nanoparticles, prepared through a co-precipitation method, were coated with phosphonic acid or iminodicarboxylic acid derivatives of calix[4]arene to modulate their surfaces with different acidic groups. Candida rugosa lipase was then directly immobilized onto the modified nanoparticles through sol-gel encapsulation. The catalytic activities and enantioselectivities of the two encapsulated lipases in the hydrolysis reaction of (R/S)-naproxen methyl ester and (R/S)-2-phenoxypropionic acid methyl ester were assessed. The results showed that the activity and enantioselectivity of the lipase were improved when the lipase was encapsulated in the presence of calixarene-based additives; the encapsulated lipase with the phosphonic acid derivative of calix[4]arene had an excellent rate of enantioselectivity against the (R/S)-naproxen methyl and (R/S)-2-phenoxypropionic acid methyl esters, with E = 350 and 246, respectively, compared to the free enzyme. The encapsulated lipases (Fe-Calix-N(COOH)) and (Fe-Calix-P) showed good loading ability and little loss of enzyme activity, and the stability of the catalyst was very good; they only lost 6-11% of the enzyme's activity after five batches.

A method to greatly improve the enantioselectivity of lipase-catalyzed hydrolysis using sodium dodecyl sulfate (SDS) as an additive

The addition of sodium dodecyl sulfate (SDS) resulted in a dramatic improvement of the enantioselectivity of the lipase-catalyzed hydrolysis of racemic butyl 2-(4-substituted phenoxy)propanoates, racemic butyl 2-(4-isobutylphenyl)propanoate, and racemic butyl 2-(6-methoxy-2-naphthyl) propanoate in an aqueous buffer solution. An increase in the E value by up to two orders of magnitude was observed for some esters. As to the effects of SDS on the structure of a lipase, FT-IR and fluorescence measurements suggest some conformational change and/or an increase of the flexibility of the lipase, although the native secondary structure of the lipase is held even in the presence of 100 mM SDS. The origin of the enantioselectivity enhancement brought about by the addition of SDS is briefly discussed on the basis of the values of the initial rates obtained for each enantiomer of the substrate.

Flash Chiral Chromatography using Carbohydrate Carbamate-coated Silica

Enantiomers of many chiral compounds are resolved rapidly on a preparative scale by passage through a column packed with flash chromatography silica which has been physically coated with a carbohydrate carbamate.

Hydrogen bonding in enantiomeric versus racemic mono-carboxylic acids; a case study of 2-Phenoxy-Propionic acid

The structural and thermodynamic backgrounds for the crystallization behaviour of racemates have been investigated using 2-phenoxypropionic acid (PPA) as an example. The racemate of PPA behaves normally and forms a racemic compound that has a higher melting point and is denser than the enantiomer. Low-temperature crystal structures of the pure enantiomer, the enantiomer cocrystallized with n-alkanes and the racemic acid showed that hydrogen-bonded dimers that form over crystallographic symmetry elements exist in all but the structure of the pure enantiomer. A database search for optically pure chiral mono-carboxylic acids revealed that the hydrogen-bonded cyclic dimer is the most prevalent hydrogen-bond motif in chiral mono-carboxylic acids. The conformation of PPA depends on the hydrogen-bond motif; the antiplanar conformation relative to the ether group is associated with a catemer hydrogen-bonding motif, whereas the more abundant synplanar conformation is found in crystals that contain cyclic dimers. Other intermolecular interactions that involve the substituent of the carboxylic group were identified in the crystals that contain the cyclic dimer. This result shows how important the nature of the substituent is for the crystal packing. The differences in crystal packing have been related to differences in melting enthalpy and entropy between the racemic and enantiomeric acids. In a comparison with the equivalent 2-(4-chlorophenoxy)-propionic acids, the differences between the crystal structures of the chloro and the unsubstituted acid have been identified and related to thermodynamic data.

Parallel kinetic resolution of 2-methoxy and 2-phenoxy-substituted carboxylic acids using a combination of quasi-enantiomeric oxazolidinones

2-Methoxy-2-phenyl acetic acid and 2-phenoxy-2-phenylpropionic acid were resolved by the parallel kinetic resolution of their corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of lithiated oxazolidinones.

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.

Preparation method of (R)-(+)-2-(4-hydroxyphenoxy) propionic acid

The invention provides a preparation method of (R)-(+)-2-(4-hydroxyphenoxy) propionic acid, and belongs to the technical field of pesticide intermediate preparation. According to the method, phenol is used as a raw material, phenol and (S)-(-)-2-halogenated propionic acid react to synthesize R-(+)-2-phenoxypropionic acid, and (R)-(+)-2-(4-hydroxyphenoxy) propionic acid is obtained after oxidation. According to the invention, the raw material phenol used in the method is low in price, the procedure operation is simple, use of hydroquinone as the raw material is avoided, and the problems of high raw material cost, difficult product purification, low yield, low product quality and need of recovery of the raw material hydroquinone caused by hydroquinone disubstituted impurities generated in the reaction when hydroquinone is used as the raw material for synthesis in the traditional method are solved; and results of the embodiment show that the yield of the (R)-(+)-2-(4-hydroxyphenoxy) propionic acid prepared by the method is greater than 85%, the liquid phase content is greater than or equal to 99.5%, the optical purity e.e is greater than 99.0%, and the product is high in yield and good in quality.

Preparation method for R-(+)-2-(4-hydroxyphenoxy)propionic acid

The invention discloses a preparation method for R-(+)-2-(4-hydroxyphenoxy)propionic acid. The method comprises the following steps: mixing phenol and S-2-chloropropionic acid or a salt of the S-2-chloropropionic acid, water and a first catalyst in a closed environment, and under the protection of an inert gas, performing heating and an alkylation reaction to prepare 2-phenoxypropionic acid; mixing the 2-phenoxypropionic acid, a second catalyst and a halogenating agent, and performing a reaction at 20-30 DEG C to prepare 2-(4-halogenated phenoxy)propionic acid; and performing a micro-pressurereaction on the 2-(4-halogenated phenoxy)propionic acid, an alkali solution and a third catalyst at 150-160 DEG C in a sealed environment, after the reaction is completed, performing filtration, and performing acidification treatment to obtain the R-(+)-2-(4-hydroxyphenoxy)propionic acid. The method provided by the invention uses the phenol and the organic acid or the organic acid salt as raw materials, and has simple purification and high purity of the product.

Chemical synthesis method of (R)-2-phenoxypropionic acid

The invention discloses a chemical synthesis method of (R)-2-phenoxypropionic acid. The chemical synthesis method comprises the following steps: performing diazotization and chlorination on L-alanineserving as a starting material to obtain (S)-2-chloropro