15573-67-8

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes:

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Acute Tox. 4 (100%)
Skin Irrit. 2 (100%)
Eye Irrit. 2A (100%)
STOT SE 3 (100%)

Usage

Uses

Used in Pharmaceutical Industry:
4-Hydroxyphenylglyoxylic acid is used as an enzyme inhibitor for its ability to inhibit enzymes involved in the biosynthesis of neurotransmitters, such as tyrosine hydroxylase and phenylalanine hydroxylase. This makes it a potential candidate for the development of drugs targeting neurological disorders.
Used in Organic Synthesis:
4-Hydroxyphenylglyoxylic acid is used as a building block in the synthesis of pharmaceutical compounds, contributing to the creation of new drugs with therapeutic potential.
Used in Dye Industry:
4-Hydroxyphenylglyoxylic acid is used as a building block for dyes, owing to its chemical structure that can be modified to produce a range of colorants for various applications.
Used in Agrochemical Industry:
4-Hydroxyphenylglyoxylic acid is utilized as a building block for agrochemicals, potentially contributing to the development of new pesticides or other agricultural chemicals.
Used in Fine Chemicals Industry:
4-Hydroxyphenylglyoxylic acid is employed as a building block for fine chemicals, which are high-purity, specialty chemicals used in various industries, including pharmaceuticals, fragrances, and flavorings.

InChI:InChI=1/C8H6O4.Na/c9-6-3-1-5(2-4-6)7(10)8(11)12;/h1-4,9H,(H,11,12);/q;+1/p-1

Upstream product

• 7099-91-4 p-methoxybenzoylformic acid 
• 6973-40-6 2,4,6-trinitrophenyl phenyl ether 
• 4755-77-5 Ethyl oxalyl chloride 
• 201230-82-2 carbon monoxide 
• 540-38-5 p-Iodophenol 
• 38250-16-7 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester 
• 99-93-4 4-Hydroxyacetophenone 
• 2628-17-3 4-Vinylphenol 
• 26787-78-0 amoxicillin 
• 70080-54-5 4-hydroxy-alpha-oxobenzeneacetic acid ethyl ester 
• 6324-01-2 p-hydroxyphenylglycine 
• 37763-23-8 D-2-p-hydroxyphenylglycine methyl ester 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 13244-75-2 (S)-α,4-dihydroxy-benzeneacetic acid 

Downstream Products

• 38250-16-7 4-hydroxy-alpha-oxobenzeneacetic acid methyl ester 
• 136205-60-2 isobutyl p-hydroxybenzoylformate 
• 156-38-7 4-hydroxyphenylacetate 
• 32462-30-9 (S)-hydroxyphenylglycine 
• 22818-40-2 D-4-hydroxyphenylglycine 
• 6324-01-2 p-hydroxyphenylglycine 
• 34917-91-4 4-hydroxyisobutyrophenone 
• 1137-42-4 4-Hydroxybenzophenone 
• 66340-55-4 (4-Hydroxy-phenyl)-[(Z)-methoxyimino]-acetic acid methyl ester 
• 840-81-3 (E)-N’-(4'-hydroxybenzylidene)isonicotinohydrazide 
• 13244-78-5 (R)-α,4-dihydroxy-benzeneacetic acid 
• 13244-75-2 (S)-α,4-dihydroxy-benzeneacetic acid 

Relevant academic research and scientific papers

ONE-STEP SYNTHESIS OF α-HYDROXY ACIDS VIA REDUCTIVE DOUBLE CARBONYLATION OF ORGANIC HALIDES

Palladium-catalyzed carbonylation of organic halides with water in the presence of calcium hydroxide or lithium hydroxide in primary or secondary alcoholic solvents afforded α-hydroxy acids.

A COMPOUND FOR THE DETERMINATION OF THE PROTEIN FKBP12 AND A SENSOR UNIT COMPRISING IT

The present invention relates to novel compounds useful as sensors for the rapid and specific determination of the FKBP12 protein, a peptidyl-prolyl cis-trans isomerase (PPlase), the levels of which in the biological fluids of a subject change if the subject is affected by pathological conditions, in particular neurodegenerative diseases, such as the Parkinson's disease and the Alzheimer's syndrome, tumour pathologies, autoimmune diseases, or if that subject is in a phase of acute rejection after organ transplantation.

Synthesis of α-Keto Acids via Oxidation of Alkenes Catalyzed by a Bifunctional Iron Nanocomposite

An efficient methodology for synthesis of α-keto acids via oxidation of alkenes using TBHP as oxidant catalyzed by a bifunctional iron nanocomposite has been established. A variety of alkenes with different functional groups were smoothly oxidized into their corresponding α-keto acids in up to 80% yield. Moreover, the bifunctional iron nanocomposite catalyst showed outstanding catalytic stability for successive recycles without appreciable loss of activity.

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

Electrochemical oxidation of amoxicillin on carbon nanotubes and carbon nanotube supported metal modified electrodes

The electrolysis of amoxicillin (AMX) was carried out on CNT, Pt/CNT and Ru/CNT modified electrodes based on Carbon Toray in 0.1 M NaOH, 0.1 M NaCl and 0.1 M Na2CO3/NaHCO3 buffer (pH 10) media with the aim of studying the significance of two factors, electrode material and pH, on the oxidative degradation and mineralization of AMX. For this purpose, the electrolysis products were identified by HPLC-MS and GC–MS, and quantified by HPLC-UV-RID and IC. The highest carbon mineralization efficiency, corresponding to 30% of the oxidized AMX, was found for Pt/CNT modified electrode in carbonate buffer medium. Regarding to the AMX conversion, the results show that the effect of pH is higher than that of the electrode material. Principal component analysis allowed to determine the experimental parameters vs. product distribution relationship and to elucidate the oxidation pathways for the studied electrodes. The results show that the hydroxylation of the aromatic ring and the nitrogen atom play an important role on the efficient degradation of AMX.

Synthesis of arylglyoxylic acids and their collision-induced dissociation

A variety of substituted arylglyoxylic acids (2a-g) were synthesized via oxidation of the corresponding aryl-methylketones (1a-e) using selenium dioxide or Friedel-Crafts acylation of phenol (3) with ethyl chlorooxoacetate and further transformations. It was found that the arylglyoxylic acids (2) undergo facile unimolecular dissociation with loss of carbon monoxide to give the corresponding arylcarboxylic acids (7) under collisionally induced mass spectrometric conditions. Copyright Taylor & Francis Group, LLC.

Novel steroid mimics: synthesis of tri- and tetra-substituted oxamides and oxoamides

A series of dicarbonyl compounds have been designed and prepared to mimic the rigid tetracyclic core of estradiol and dihydrotestosterone. Non-symmetrical tri- and tetra-substituted oxamides were prepared by the sequential addition of primary and secondary amines to phenyl cholorooxoacetate. Oxoamides were prepared via a Friedel-Crafts acylation/amide coupling protocol. Crystallographic data shows a good correlation between the structure of the dicarbonyl mimic and dihydrotestosterone complexed with the androgen receptor suggesting the molecular scaffolds may well prove versatile platforms for ligand design.

Divalent and trivalent α-ketocarboxylic acids as inhibitors of protein tyrosine phosphatases

Protein tyrosine phosphatases (PTPases) are important targets for the treatment of insulin resistance in patients with type II diabetes and as antibacterial agents. As a result, there is a growing interest in the development of potent and specific inhibitors for these enzymes. This paper describes a series of inhibitors that contain two or three α-ketocarboxylic acid groups that are designed to form multiple contacts with residues inside or near the active site of phosphatases. The inhibitors have been assayed against three PTPases: the Yersinia PTPase, PTP1B, and LAR. The best of the inhibitors has IC50 values against the Yersinia PTPase and PTP1B of 0.7 and 2.7 μM, respectively. These divalent and trivalent compounds are significantly more potent than their corresponding monovalent analogues. In addition, they show good selectivity for PTP1B and the Yersinia PTPase as compared to LAR.

Characterisation of a hydroxymandelate oxidase involved in the biosynthesis of two unusual amino acids occurring in the vancomycin group of antibiotics.

ORF22 from the chloroeremomycin gene cluster has been cloned, expressed and characterised as a hydroxymandelate oxidase (HmO) that is involved in the formation of both (S)-4-hydroxyphenylglycine and (S)-3,5-dihydroxyphenylglycine.

S,N-COMPOUNDS VIA AMINES AND SULPHUR HALIDES

The many products got by reactions of amines with sulfur halides are discussed.Special attention is given to the intermediate thionitroso compounds, the N-thiosulfinylamines and the persistent radicals 1,2,3-dithiazolyles.New results about the course of the HERZ reaction are described.