28173-23-1

Usage

Uses

Used in Pharmaceutical Industry:
(2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid is used as an intermediate in the synthesis of various pharmaceutical compounds. Its involvement in the tyrosine metabolism pathway makes it a key component in the production of neurotransmitters, which are essential for proper brain function and communication.
Used in Nutraceutical Industry:
In the nutraceutical industry, (2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid is used as a dietary supplement or ingredient in functional foods. Its role in the biosynthesis of phenylalanine and tyrosine contributes to the maintenance of optimal health and well-being. Additionally, its involvement in melanin synthesis may have potential applications in skin health and pigmentation regulation.
Used in Research and Development:
(2Z)-4-[(4-hydroxyphenyl)amino]-4-oxobut-2-enoic acid is utilized in research and development for studying the tyrosine metabolism pathway and its related biological processes. Understanding its role in neurotransmitter production and melanin synthesis can lead to the discovery of new therapeutic targets and applications in medicine and healthcare.

Upstream product

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

Downstream Products

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

Relevant academic research and scientific papers

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.

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds

Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.

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.

Solvent free preparation of n-substituted maleanilic acid

Six N-maleanilic acids namely N-(4-carboxy)maleanilic acid (CAMAA), N-(4- bromo)maleanilic acid (BMAA), N-(4-hydroxy)maleanilic acid (HMAA), N-(3-hydroxy)maleanilic acid (mHMAA), N-(4-chloro)maleanilic acid (CMAA) and N-(4-methyl)maleanilic acid (MMAA) we

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.

A facile and economical procedure for the synthesis of maleimide derivatives using an acidic ionic liquid as a catalyst

Seven maleimide derivatives were synthesized in good yields and high purity from the corresponding maleamic acids using a Bronsted acidic room temperature ionic liquid (RTIL) as a catalyst. The products were obtained through merely a decanting and removal of the solvent, suggesting that this procedure is superior to the conventional routes, in which the strong organic/inorganic acids were used as the catalysts, as well as a complicated post-processing procedure for the separation and purification of the products was employed.

Reactivity studies of maleimide epoxy resin with long chained amines

After phenylmaleimido group was successfully incorporated into bisphenol-A type epoxy resins (B-13 ) to result in compound possessing both oxirane ring and maleimide reactive groups. The cured maleimide epoxy samples are obtained by thermally curing of the maleimide epoxy (MIE) compounds with aliphatic long chained amines such as Tetraethylenepentamine (TEPA), Bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) exhibited excellent thermal stability and good chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.

Synthesis of co(II), Ni(II) and Cu(II) complexes from schiff base ligand and reactivity studies with thermosetting epoxy resin

A hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) containing Co(II), Ni(II) and Cu(II) ions was prepared by curing N-MPGE and tetradentate Schiff base Co(II), Ni(II) and Cu(II) complexes. The curing polymerization reaction of N-MPGE with metal complexes as curing agents was studied. The cured samples were studied for thermal stability, chemical (acid/alkali/solvent) and water absorption resistance and homogeneity of the cured systems. The tetradentate Schiff base, 3-[(Z)-2-piperazin-1-yl- ethylimino]-1,3-dihydro indol-2-one was synthesized by the condensation of Isatin (Indole-2, 3-dione) with 1-(2-aminoethyl)piperazine (AEP). Its complexes with Co(II), Ni(II) and Cu(II) have been synthesized and characterized by microanalysis, conductivity, Uv-Visible, FT-IR, TGA and magnetic susceptibility measurements. The spectral data revealed that the ligand acts as a neutral tetradentate Schiff base and coordinating through the azomethine nitrogen, two piperazine nitrogen atoms and carbonyl oxygen.

Preparation and reactivity studies of maleimidophenyl glycidylether with amines

The hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) was prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possessed both the oxirane ring and maleimide group. The curing reaction of N-MPGE with amines as curing agents such as tetraethylenepentamine (TEPA), bishexamethylenetriamine (BHMT), 2-methyl pentamethylenediamine (2-MPMDA) and 2,2,4-trimethy diamines (2,2,4-TMDA) was studied. The cured samples exhibited good thermal stability and excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity network of the cured systems.

Synthesis, characterization and curing studies of thermosetting epoxy resin with amines

A new hybrid thermosetting maleimido epoxy compound 4-(N-maleimidophenyl) glycidylether (N-MPGE) is prepared by reacting N-(4-hydroxyphenyl) maleimide (HPM) with Epichlorohydrin by using benzyltrimethylammonium chloride as a catalyst. The resulting compound possesses both the oxirane ring and maleimide group. The curing reaction of these maleimidophenyl glycidylether epoxy compound (N-MPGE) with amines as curing agents such as ethylendiamine (EDA), diethylentriamine (DETA) and triethylenetetramine (TETA), aminoethylpiperazine (AEP) and isophoronediamine, IPDA), are studied. Incorporation of maleimide groups in the epichlorohydrin provides cyclic imide structure and high cross-linking density to the cured resins. The cured samples exhibited good thermal stability, excellent chemical (acid/alkali/solvent) and water absorption resistance. Morphological studies by the SEM technique further confirmed the phase homogeneity net work of the cured systems.