28173-23-1

Basic information

• Product Name: (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid
• Synonyms: (2Z)-4-[(4-Hydroxyphenyl)amino]-4-oxobut-2-enoic acid; 2-butenoic acid, 4-[(4-hydroxyphenyl)amino]-4-oxo-, (2Z)-
• CAS NO: 28173-23-1
• Molecular Formula: C₁₀H₉NO₄
• Molecular Weight: 207.1828
• Mol File: 28173-23-1.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 520.6°C at 760 mmHg
• Flash Point: 268.7°C
• Density: 1.456g/cm³
• Vapor Pressure: 1.15E-11mmHg at 25°C
• Refractive Index: 1.672
• CAS DataBase Reference: (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid(28173-23-1)
• EPA Substance Registry System: (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid(28173-23-1)

Safety Data

• Hazardous Substances Data: 28173-23-1(Hazardous Substances Data)

Usage

General Description

The chemical (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid, also known as hydroxyphenylpyruvate, is a compound with the molecular formula C10H9NO4. It is a derivative of pyruvic acid and contains a hydroxyphenyl group. (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid is involved in the tyrosine metabolism pathway and is a precursor in the biosynthesis of phenylalanine and tyrosine. It plays a crucial role in various biological processes, including the production of neurotransmitters and the synthesis of melanin. Additionally, it has potential applications in the pharmaceutical and nutraceutical industries, making it an important chemical compound with diverse biological and industrial significance.

Upstream product

• 108-31-6 maleic anhydride 
• 123-30-8 4-amino-phenol 
• 67-64-1 acetone 
• 71-43-2 benzene 

Downstream Products

• 906352-14-5 N-p-acetoxy-phenylisomaleimide 
• 6637-46-3 4-(acetoxyphenyl)maleimide 
• 915711-53-4 (E)-3-(4-Hydroxy-phenylcarbamoyl)-acrylic acid methyl ester 
• 915711-45-4 (Z)-3-(4-Hydroxy-phenylcarbamoyl)-acrylic acid methyl ester 
• 7300-91-6 N-(4-hydroxyphenyl)maleimide 

Relevant articles and documents

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation

A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.

Potent Nematicidal Activity of Maleimide Derivatives on Meloidogyne incognita

Different maleimide derivatives were synthesized and assayed for their in vitro activity on the soil inhabiting, plant-parasitic nematode Meloidogyne incognita, also known as root-knot nematode. The compounds maleimide, N-ethylmaleimide, N-isopropylmaleimide, and N-isobutylmaleimide showed the strongest nematicidal activity on the second stage juveniles of the root-knot nematode with EC50/72h values of 2.6 ± 1.3, 5.1 ± 3.4, 16.2 ± 5.4, and 19.0 ± 9.0 mg/L, respectively. We also determined the nematicidal activity of copper sulfate, finding an EC50 value of 48.6 ± 29.8 mg/L. When maleimide at 1 mg/L was tested in combination with copper sulfate at 50 mg/L, we observed 100% mortality of the nematodes. We performed a GC-MS metabolomics analysis after treating nematodes with maleimide at 8 mg/L for 24 h. This analysis revealed altered fatty acids and diglyceride metabolites such as oleic acid, palmitic acid, and 1-monopalmitin. Our results suggest that maleimide may be used as a new interesting building block for developing new nematicides in combination with copper salts.

Synthesis and characterization of schiff base metal complexes and reactivity studies with malemide epoxy resin

A novel malemide epoxy containing Co(II), Ni(II) and Cu(II) ions have been synthesized by curing malemide epoxy resin (MIEB-13) and Co(II), Ni(II) and Cu(II) complexes of macrocyclic bis-hydrazone Schiff base. The Schiff base was synthesized by reacting 1,4-dicarbnyl phenyl dihydrazide with 2,6-diformyl-4-methyl phenol. The Schiff base and its Co(II), Ni(II) and Cu(II) complexes have been characterized by elemental analyses, spectral (IR, 1H NMR, UV-vis., FAB mass, ESR), thermal and magnetic data. The curing reaction of maleimide epoxy compound with metal complexes was studied as curing agents. The stability of cured samples was studied by thermo-gravimetric analyses and which have excellent chemical (acid/alkali/solvent) and water absorption resistance. Further, the scanning electron microscopy (SEM) and definitional scanning colorimetric (DSC) techniques were confirmed the phase homogeneity of the cured systems.