31284-89-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Hydroxy-2-(4-methylphenyl)acetic acid is used as an anti-inflammatory agent for the treatment of conditions such as arthritis, tendinitis, bursitis, and gout. It serves to reduce the body's immune response to these conditions, thereby diminishing symptoms and enhancing patient comfort.
Used in Pain Management:
In the healthcare sector, 2-Hydroxy-2-(4-methylphenyl)acetic acid is utilized as an analgesic to manage mild to moderate pain by decreasing the body's production of prostaglandins, which are linked to pain sensation.
It is important to follow medical advice when using tolmetin and to be conscious of potential side effects and drug interactions to ensure safe and effective treatment.

InChI:InChI=1/C9H10O3/c1-6-2-4-7(5-3-6)8(10)9(11)12/h2-5,8,10H,1H3,(H,11,12)/t8-/m1/s1

Upstream product

• 412014-15-4 diethyl 2-hydroxy-2-(4-methylphenyl)propane-1,3-dioate 
• 18584-23-1 hydroxy-p-tolyl-acetic acid ethyl ester 
• 104-87-0 4-methyl-benzaldehyde 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 23786-13-2 methyl p-tolylacetate 
• 201230-82-2 carbon monoxide 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 
• 66985-49-7 2-(4-methylphenyl)-2-(trimethylsilyloxy)acetonitrile 
• 70122-96-2 (2,2,2-Trichloro-1-p-tolyl-ethyl)-carbamic acid methyl ester 
• 102862-46-4 3-p-Tolyl-oxirane-2,2-dicarbonitrile 
• 67-66-3 chloroform 
• 128042-09-1 (2,2,2-Tribromo-1-p-tolyl-ethyl)-carbamic acid ethyl ester 
• 77785-22-9 Methoxymethoxy-p-tolyl-acetic acid ethyl ester 

Downstream Products

• 13305-13-0 methyl (+/-)-α-hydroxy-α-(4-methylphenyl)acetate 
• 18584-20-8 (R)-para-methylmandelic acid 
• 145297-16-1 acetoxy-p-tolyl-acetic acid 
• 37135-54-9 2,2-diethyl-5-p-tolyl-[1,3,2]dioxasilolan-4-one 
• 25297-16-9 2-bromo-2-(p-tolyl)acetic acid 
• 91143-62-3 (+)-p-methyl-O-acetylmandelic acid 
• 18584-20-8 (-)-p-methylmandelic acid 
• 7163-50-0 (4-methylphenyl)(oxo)acetic acid 
• 10295-44-0 2-hydroxy-N-phenyl-2-(p-tolyl)acetamide 
• 15674-78-9 (+/-)-α-bromo-p-tolylacetic acid ethyl ester 
• 530091-80-6 benzyl 2-bromo-2-(p-tolyl)acetate 
• 101789-22-4 mesityl-p-tolyl ketene 
• 101742-91-0 2-mesityl-2-p-tolyl-vinyl alcohol 
• 103045-94-9 benzoic acid-(2-mesityl-2-p-tolyl-vinyl ester) 

Relevant academic research and scientific papers

Reductive Coupling of Carbon Dioxide and an Aldehyde Mediated by a Copper(I) Complex toward the Synthesis of α-Hydroxycarboxylic Acids

Copper-mediated reductive coupling between CO2 and an aldehyde to form α-hydroxycarboxylic acid was achieved using silylborane as a reductant. CO2 cleanly inserted into a copper-carbon bond that was formed by the reaction between a silylcopper-NHC complex

Highly Efficient Deracemization of Racemic 2-Hydroxy Acids in a Three-Enzyme Co-Expression System Using a Novel Ketoacid Reductase

Enantiopure 2-hydroxy acids (2-HAs) are important intermediates for the synthesis of pharmaceuticals and fine chemicals. Deracemization of racemic 2-HAs into the corresponding single enantiomers represents an economical and highly efficient approach for synthesizing chiral 2-HAs in industry. In this work, a novel ketoacid reductase from Leuconostoc lactis (LlKAR) with higher activity and substrate tolerance towards aromatic α-ketoacids was discovered by genome mining, and then its enzymatic properties were characterized. Accordingly, an engineered Escherichia coli (HADH-LlKAR-GDH) co-expressing 2-hydroxyacid dehydrogenase, LlKAR, and glucose dehydrogenase was constructed for efficient deracemization of racemic 2-HAs. Most of the racemic 2-HAs were deracemized to their (R)-isomers at high yields and enantiomeric purity. In the case of racemic 2-chloromandelic acid, as much as 300 mM of substrate was completely transformed into the optically pure (R)-2-chloromandelic acid (> 99% enantiomeric excess) with a high productivity of 83.8 g L?1 day?1 without addition of exogenous cofactor, which make this novel whole-cell biocatalyst more promising and competitive in practical application.

The Synthesis of Chiral α-Aryl α-Hydroxy Carboxylic Acids via RuPHOX-Ru Catalyzed Asymmetric Hydrogenation

A ruthenocenyl phosphino-oxazoline-ruthenium complex (RuPHOX?Ru) catalyzed asymmetric hydrogenation of α-aryl keto acids has been successfully developed, affording the corresponding chiral α-aryl α-hydroxy carboxylic acids in high yields and with up to 97% ee. The reaction could be performed on a gram scale with a relatively low catalyst loading (up to 5000 S/C) and the resulting products can be transformed to several chiral building blocks, biologically active compounds and chiral drugs. (Figure presented.).

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

Silica sulfuric acid as a highly efficient catalyst for the synthesis of diarylacetic acids

ABSTRACT: An efficient heterogeneous method for the synthesis of diarylacetic acids was developed utilizing silica sulfuric acid as a catalyst. The reaction is highly efficient with a small amount of catalyst for the combination of a variety of electron-n

Asymmetric hydrogenation reaction of alpha-ketoacids compound

The invention relates to the technical field of organic chemistry, especially to an asymmetric hydrogenation reaction of an alpha-ketoacids compound. The asymmetric hydrogenation reaction comprises a scheme shown in the description. In the scheme, R1 is phenyl, substituted phenyl, naphthyl, substituted naphthyl, C1-C6 alkyl, or aralkyl; a substituent group is C1-C6 alkyl, C1-C6 alkoxy, or halogen; and the number of the substituent group is 1-3. In the scheme, M is a chiral spiro-pyridylamino phosphine ligand iridium complex having a structure shown in the description. In the structure, R is hydrogen, 3-methyl, 4-tBu, or 6-methyl.

Solid phase behavior in the chiral systems of various 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives

The solid phase behavior of a series of monosubstituted F-, Cl-, Br-, I-, and CH3- and two 2,4-halogen-disubstituted 2-hydroxy-2-phenylacetic acid (mandelic acid) derivatives was investigated. The study includes detailed information about melting temperature, melting enthalpy, X-ray diffraction data, as well as selected binary phase diagrams of the respective chiral systems. Aside from the known metastable conglomerate 2-chloromandelic acid, evidence for two more metastable conglomerates was found.

Kinetic resolution of mandelate esters via stereoselective acylation catalyzed by lipase PS-30

By using lipase PS-30 as catalyst, the kinetic resolution of a series of racemic mandelate esters has been achieved via stereoselective acylation. The value of kinetic enantiomeric ratio (E) reached up to 197.5. Substituent effect is briefly discussed.

Relationships between the racemic structures of substituted mandelic acids containing 8- and 10-membered hydrogen bonded dimer rings

The structures of 27 monosubstituted mandelic acids, including several of their polymorphs, plus unsubstituted mandelic acid itself (two polymorphs) are investigated for structural similarity. The results, presented pictorially as a structural relationship plot, show that rather more structures are built up from the carboxyl-chain hydroxyl hydrogen bonded dimer than from the conventional carboxylic acid dimer. The results show how all the structures are related and, based on the two types of dimer, the degree of similarity that they possess. Some structures with Z′ > 1 contain both sorts of dimers and there are many examples of isostructural sets within the structures so far determined. We also present an example where analysing similarity in related families of structures highlights a structure that should be present and which has indeed then proceeded to be synthesised and determined.

Carboxylation with CO2 via brook rearrangement: Preparation of α-hydroxy acid derivatives

In the presence of CsF, a wide range of α-substituted α-siloxy silanes were carboxylated under a CO2 atmosphere (1 atm) via Brook rearrangement. A variety of α-substituents including aryl, alkenyl, and alkyl groups were tolerated to afford α-hydroxy acids in moderate-to-high yields. One-pot synthesis from aldehydes using PhMe2SiLi and CO 2 was also possible, providing α-hydroxy acids without the isolation of an α-hydroxy silane.