17057-04-4

Basic information

• Product Name: 4-Maleimidobenzoic acid
• Synonyms: ART-CHEM-BB B006486;AKOS B006486;AKOS MSC-0031;4-MALEIMIDOBENZOIC ACID;4-(2,5-DIHYDRO-2,5-DIOXO-1HPYRROL-1YL)-BENZOIC ACID;4-(2,5-DIOXO-2,5-DIHYDRO-1H-PYRROL-1-YL)BENZOIC ACID;4-(2,5-DIOXO-2,5-DIHYDRO-PYRROL-1-YL)-BENZOIC ACID;N-(4-CARBOXYPHENYL)MALEIMIDE
• CAS NO: 17057-04-4
• Molecular Formula: C₁₁H₇NO₄
• Molecular Weight: 217.18
• EINECS: 241-117-9
• Product Categories: Miscellaneous;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
• Mol File: 17057-04-4.mol
• Article Data: 44

Chemical Properties

• Melting Point: 225-228 °C
• Boiling Point: 447.1 °C at 760 mmHg
• Flash Point: 224.2 °C
• Appearance: /
• Density: 1.521 g/cm³
• Vapor Pressure: 8.92E-09mmHg at 25°C
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• PKA: 3.93±0.10(Predicted)
• CAS DataBase Reference: 4-Maleimidobenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Maleimidobenzoic acid(17057-04-4)
• EPA Substance Registry System: 4-Maleimidobenzoic acid(17057-04-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 17057-04-4(Hazardous Substances Data)

Usage

General Description

4-Maleimidobenzoic acid is a chemical compound that contains a maleimide functional group and a benzoic acid group. It is commonly used in bioconjugation and crosslinking reactions in chemistry and biochemistry. The maleimide group is reactive towards thiol groups, which makes it useful for linking proteins, peptides, and other biomolecules together. The benzoic acid group also provides additional reactivity and versatility, making 4-Maleimidobenzoic acid a popular choice for modifying and functionalizing biomolecules for various applications in research and industry. Overall, the compound's unique and versatile reactivity make it an important tool in bioconjugation and chemical biology research.

InChI:InChI=1/C11H7NO4/c13-9-5-6-10(14)12(9)8-3-1-7(2-4-8)11(15)16/h1-6H,(H,15,16)/p-1

Upstream product

• 5432-04-2 N-(4-carboxyphenyl)maleamic acid 
• 108-31-6 maleic anhydride 
• 62-23-7 4-nitro-benzoic acid 
• 36847-93-5 4-{[3-carboxyprop-2-enoyl]amino}benzoic acid 
• 150-13-0 4-amino-benzoic acid 
• 108-24-7 acetic anhydride 
• 110-16-7 maleic acid 
• 5432-04-2 4-(3-carboxy-acryloylamino)-benzoic acid 

Downstream Products

• 29305-46-2 4-(2,5-dioxo-2,5-dihydro-1-pyrrol-1-yl)benzoyl chloride 
• 97670-49-0 N-Maleoyl-4-aminobenzoesaeure-2,4-dinitrophenylester 
• 73431-46-6 N-Maleoyl-4-aminobenzoesaeure-4-nitrophenylester 
• 143729-46-8 N-(p-carboxyphenyl)maleopimarimide 
• 101413-80-3 5-Carboxy-3-oxo-tetrahydro-1,4-thiazin-2-yl-acetyl-4-amino-benzoesaeure 
• 101413-82-5 Mal-Pab-Gly-OEt 
• 101413-84-7 Mal-Pab-L-Phe-OMe 
• 101413-83-6 Mal-Pab-Gly-Gly-OEt 
• 101413-85-8 Mal-Pab-Asp(OMe)2 
• 101413-78-9 2-Imino-thiazolid-4-on-5-yl-acetyl-4-amino-benzoesaeure 
• 101413-74-5 3-Oxo-2,3-dihydro-1,4-benzothiazin-2-yl-acetyl-4-aminobenzoesaeure 
• 101413-71-2 N-Maleoyl-4-aminobenzoesaeure-2-nitrophenylester 
• 101413-77-8 2-Phenyl-imino-thiazolid-4-on-5-yl-acetyl-4-amino-benzoesaeure 
• 97654-03-0 Mal-Pab-Tyr-OMe 

Relevant articles and documents

4-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoic acid: X-ray and DFT-calculated structure

In the title compound, C11H7NO4, there is a dihedral angle of 45.80 (7)° between the planes of the benzene and maleimide rings. The presence of O - H...O hydrogen bonding and weak C - H...O inter-actions allows the formation of R33(19) edge-connected rings parallel to the (010) plane. Structural, spectroscopic and theoretical studies were carried out. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) and 6-31++G(d,p) levels are compared with the experimentally determined mol-ecular structure in the solid state. Additional IR and UV theoretical studies allowed the presence of functional groups and the transition bands of the system to be identified.

Preparation and characterization of new carrier drug polymers based maleimide and its drug release behaviour

In this work, two new drug substituted monomers and new homogenous and heterogeneous polymers were synthesized loaded with medicinal properties to extend the controlled drug. The first step includes preparation of compound (F1) via reaction of maleic anhydride with 4-aminobenzoic acid. Then compound (F1) was converted to its corresponding acyl chloride derivative which reacted with amino drugs (sulfadiazine, chlordiazepoxide) afforded (F2 and F3) monomers. Homogeneous polymers (F8 and F9) prepared through polymerization reaction of free radicals of the monomers (F2 and F3) under nitrogen using methyl ethyl ketone peroxide (MEKP) as initiator. Heterogeneous polymers (F14 and F15) prepared through polymerization reaction of free radicals of the monomers (F2 and F3) separately with acrylic acid under nitrogen using methyl ethyl ketone peroxide (MEKP) as initiator. All these prepared monomers and polymers were characterized by FT-IR and 1H NMR, 13C NMR spectroscopies. Controlled drug release and swelling % was studied in different pH values at 37 oC. Intrinsic viscosities were measured at 25 oC with Ostwald viscometer and applied the characteristic of solubility for these polymers.

Synthesis and evaluation of a novel fluorescent chemosensor for glutathione based on a rhodamine B and N-[4-(carbonyl) phenyl]maleimide conjugate and its application in living cell imaging

A novel rhodamine B spirolactam derivative bearing an N-[4-(carbonyl)phenyl] maleimide moiety (L1) was designed, synthesized and structurally characterized to develop a chemosensor. The interactions of L1 with amino acids and metal ions were studied by UV–vis absorption and fluorescence spectroscopy. L1 exhibited a highly sensitive and selective turn-on fluorescence response toward glutathione (GSH) over other biological species in EtOH/HEPES (3:2, v/v, 0.1?mM, pH 7.34) solution. The detection limit of GSH by L1 was 0.219?μM. Intracellular imaging applications demonstrated that L1 can be used as a fluorescent probe for the detection of GSH in HepG-2 and HUVEC cells.

A NIR facile, cell-compatible fluorescent sensor for glutathione based on Michael addition induced cascade spirolactam opening and its application in hepatocellular carcinoma

A NIR fluorescence probe with long emission wavelength at 746 nm and high quantum yield of 0.36 was designed and synthesized to selectively detect GSH over Hcy and Cys in living systems. 2-(1,3,3-Trimethylindolin-2-ylidene)acetaldehyde was attached to rhodamine by Knoevenagel condensation to shift the emission to near infrared region. Then, ethylenediamine was linked to M2 get an important intermediate M3. Finally, target molecule named RhNM was synthesized through combined N-[4-(carbonyl)phenyl] with M3. RhNM shows excellent discrimination in detecting GSH from Hcy/Cys along with an obvious color change. The fluorescence band at 746 nm is rapidly enhanced 106-fold after adding GSH, and the quantum was calculated at 0.36. Titration experiments of GSH showed good linear relationship of intensity vs. GSG concentration, and the detection limit was calculated at 70 nM. The proposed mechanism for identifying GSH based on Michael addition involves reactions of the carbon-carbon double bond and subsequent spirolactam opening. Meanwhile, the probe RhNM can work in a wide range of pH of 4-10. The probe RhNM was used for endogenous and exogenous imaging in HepG2 cells for glutathione. There was an outstanding intracellular red fluorescence occurring upon the addition of GSH incubated with HepG2 cells. It has been successfully applied for the determination of GSH in diluted serum and for bio-imaging of GSH in living cells with low cell toxicity. All results indicated that the probe can be used as an ultra-sensitive, near-infrared fluorescent chemical sensor for selectively detecting GSH in living cell. It has great potential in imaging of live tissues and even, animal imaging.

1,3-dipolar cycloaddition: Free catalytic synthesis and esophageal cancer activity of new 1,2,3-triazole-oxydianiline-maleimide hybrids

A new series of 1,2,3-triazole-oxydianiline-maleimide hybrids 12-15 was synthesized by using 1,3-dipolar cycloaddition reaction of N-Arylmaleimides 6-9 with 4,4'-oxybis(azidobenzene) 11 under an efficient and free catalytic reaction. All the newly synthesized hybrids were characterized by their 1H NMR, F-TIR, Mass spectral data and melting points. The cytotoxic activities (in vitro) of selected hybrids against esophageal cancer of human cell line (SKG) were evaluated by MTT assay. Among them, hybrid 13 exhibited a potent inhibition activity with the IC50 value of 1.61±0.01 μM against esophageal cancer cell (SKG). Cellular mechanism investigations in esophageal carcinoma cells (SKG) elucidated that hybrid 13 inhibited cell growths in vitro and arrested cell cycle at an environmental phase. These results revealed that hybrid 13 holds a promising anticancer agent with the enhancement of further clinical applications in drug discovery field.

AMINOBENZOIC ACID DERIVATIVES FOR USE AS ANTI-INFLAMMATORY AGENTS, ANTI-METASTATIC AGENTS AND/OR ANTICANCER AGENTS

There are provided compounds of formula (IF) in which R2 and R11 can represent various different possibilities. These compounds can be useful as anticancer agents as well as anti-inflammatory agents, anti-proliferative agents and/or anti-metastatic agents.