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4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid, also known as N-(4-carboxyphenyl)maleimide, is a chemical compound with the molecular formula C11H7NO4. It is a yellow crystalline solid that is soluble in water and various organic solvents. 4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid is primarily used as a protein cross-linking reagent, particularly for the modification of cysteine residues in proteins. It forms covalent bonds with thiol groups, leading to the stabilization of protein structures and the prevention of protein degradation. Due to its reactivity with thiols, it is also used in the study of protein folding and conformational changes. The compound is synthesized through a series of chemical reactions involving the condensation of 4-aminobenzoic acid with maleic anhydride, followed by hydrolysis to obtain the final product. It is an important tool in biochemistry and molecular biology research, providing insights into protein structure and function.

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  • 5432-04-2 Structure
  • Basic information

    1. Product Name: 4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid
    2. Synonyms: 4-{[(2E)-3-Carboxyprop-2-enoyl]amino}benzoic acid; benzoic acid, 4-[[(2E)-3-carboxy-1-oxo-2-propen-1-yl]amino]-
    3. CAS NO:5432-04-2
    4. Molecular Formula: C11H9NO5
    5. Molecular Weight: 235.1929
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 5432-04-2.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 564.7°C at 760 mmHg
    3. Flash Point: 295.3°C
    4. Appearance: N/A
    5. Density: 1.504g/cm3
    6. Vapor Pressure: 1.38E-13mmHg at 25°C
    7. Refractive Index: 1.669
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. CAS DataBase Reference: 4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid(CAS DataBase Reference)
    11. NIST Chemistry Reference: 4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid(5432-04-2)
    12. EPA Substance Registry System: 4-{[(2E)-3-carboxyprop-2-enoyl]amino}benzoic acid(5432-04-2)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 5432-04-2(Hazardous Substances Data)

5432-04-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 5432-04-2 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 5,4,3 and 2 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 5432-04:
(6*5)+(5*4)+(4*3)+(3*2)+(2*0)+(1*4)=72
72 % 10 = 2
So 5432-04-2 is a valid CAS Registry Number.

5432-04-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-[[(E)-3-carboxyprop-2-enoyl]amino]benzoic acid

1.2 Other means of identification

Product number -
Other names 4'-carboxymaleanilic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:5432-04-2 SDS

5432-04-2Relevant articles and documents

Covalent conjugation of single-walled carbon nanotube with CYP101 mutant for direct electrocatalysis

Ray, Moumita,Mhaske, Sanjay D.,Haram, Santosh K.,Mazumdar, Shyamalava

, (2021/05/10)

Covalent linkage between the single-walled carbon nanotube (SWCNT) and CYP101 through a specific site of the enzyme can provide a novel method of designing efficient enzyme electrodes using this prototype cytochrome P450 enzyme. We have chemically modified the SWCNT with linker 4-carboxy phenyl maleimide (CPMI) containing maleimide functional groups. The enzyme was covalently attached on to the SWCNT through the maleimide group of the linker (CPMI) to the thiolate group of the surface exposed Cys 58 or Cys 136 of the CYP101 forming a covalently immobilized protein on the nanotube. Thin film of the modified SWCNT-CPMI-CYP101conjugate was made on a glassy carbon (GC) electrode. Direct electrochemistry of the substrate (camphor)-bound enzyme was studied using this immobilized enzyme electrode system and the redox potential was found to be ?320mV vs Ag/AgCl (3 M KCl), which agrees with the redox potential of the substrate bound enzyme reported earlier. The electrochemically driven enzymatic mono-oxygenation of camphor by this immobilized enzyme electrode system was studied by measurement of the catalytic current at different concentrations of camphor. The catalytic current was found to increase with increasing concentration of camphor in presence of oxygen. The product formed during the catalysis was identified by mass-spectrometry as hydroxy-camphor.

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

Mohammed, Mohammed K.,Almashal, Faeza A.,Jassem, Ahmed M.

, p. 47 - 53 (2021/01/18)

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.

The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes

Oktay, Koray,K?se, Leyla Polat,?endil, K?v?lc?m,Gültekin, Mehmet Serdar,Gül?in, ?lhami,Supuran, Claudiu T.

, p. 939 - 945 (2016/10/09)

The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acid (4) derivatives containing structural characteristics that can be used for the synthesis of several active molecules, is presented. Some of the butenoic acid derivatives (4a, 4c, 4e, 4i, 4j, 4k) are

Solvent free preparation of n-substituted maleanilic acid

Saedi, Habib

, p. 137 - 141 (2013/08/24)

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 evaluation of novel 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-diones for advanced glycation end product formation inhibitory activity

Kaur, Anjandeep,Singh, Baldev,Jaggi, Amteshwar Singh

supporting information, p. 797 - 801 (2013/02/25)

The synthesis of some biologically interesting pyrrolo-isoxazolidine derivatives was accomplished by the 1,3-dipolar cycloaddition reaction of substituted azomethine N-oxides 1 with substituted N-aryl maleimides 2 leading to the formation of new stereoisomeric 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives 3 in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay. All the synthesized compounds have been found to exhibit significant activity against AGE formation.

Novel antimicrobial organic thermal stabilizer and co-stabilizer for rigid PVC

Fahmy, Mona M.,Mohamed, Riham R.,Mohamed, Nadia A.

experimental part, p. 7927 - 7940 (2012/10/08)

Biologically active N-benzoyl-4-(N-maleimido)-phenylhydrazide (BMPH) was synthesized and its structure was confirmed by elemental analysis and various spectral tools. It was examined as a thermal stabilizer and co-stabilizer for rigid poly (vinyl chloride) at 180°C in air. Blending BMPH with reference samples in different ratios greatly lengthens the thermal stability value and improves the extent of discoloration of PVC. TGA confirmed the improved stability of PVC in presence of the investigated organic stabilizer. GPC measurements were done to investigate the changes occurred in the molecular masses of the degraded samples of blank PVC and PVC in presence of the novel stabilizer. BMPH showed good antimicrobial activity towards two kinds of bacteria and two kinds of fungi.

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

Li, Kai,Yuan, Chao,Zheng, Shijun,Fang, Qiang

experimental part, p. 4245 - 4247 (2012/08/28)

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.

In situ formation of N-trifluoroacetoxy succinimide (TFA-NHS): One-pot formation of succinimidyl esters, N-trifluoroacetyl amino acid succinimidyl esters, and N-maleoyl amino acid succinimidyl esters

Leonard, Nicholas M.,Brunckova, Jarmila

supporting information; experimental part, p. 9169 - 9174 (2011/12/16)

A method for the in situ formation of N-trifluoroacetoxy succinimide (TFA-NHS) and its application in the formation of succinimidyl esters is presented. The developed method provides N-trifluoroacetyl and N-maleoyl amino acid succinimidyl esters from a variety of amino acids using a one-pot, high-yielding protocol. Investigations into the formation of an N-maleoyl amino acid succinimidyl ester supported the proposal of a revised reaction mechanism, and contributed to the optimization of the reaction conditions.

Synthesis of Diels-Alder adducts of N-arylmaleimides by a multicomponent reaction between maleic anhydride, dienes, and anilines

Guevara-Salazar, J. Alberto,Quintana-Zavala, Delia,Jimenez-Vazquez, Hugo A.,Trujillo-Ferrara, Jose

experimental part, p. 827 - 836 (2012/07/27)

We have carried out the synthesis and characterization of some hexahydroisoindolyl benzoic acids and their corresponding ethyl esters by a multicomponent reaction (MCR) between aminobenzoic acids or aminobenzoates, maleic anhydride, and isoprene in the ab

Design, synthesis, and biological evaluation of N-carboxyphenylpyrrole derivatives as potent HIV fusion inhibitors targeting gp41

Liu, Kun,Lu, Hong,Hou, Ling,Qi, Zhi,Teixeira, Cátia,Barbault, Florent,Fan, Bo-Tao,Liu, Shuwen,Jiang, Shibo,Xie, Lan

experimental part, p. 7843 - 7854 (2009/11/30)

On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydroxy)phenyl-2,5-dimethylpyrrole (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A1, NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that 11 compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A12), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A12 could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.

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