3-Maleimido-benzoic acid contains a benzoic acid core bearing a maleimide substituent, classifying it as a structurally modified aromatic acid rather than a free amino acid or a peptide building block. The molecule features a carboxylic acid functional group alongside the electrophilic maleimide ring, which provides a defined carbon-carbon/heteroatom reactive handle for conjugation chemistry, while no amino or amino-acid stereocenters are indicated by the name. In research and synthesis contexts, it is employed as a functional aromatic acid precursor and as a maleimide-bearing coupling reagent for preparing benzoate-linked conjugates, including materials and biomolecule labeling strategies that require a stable carboxyl group and a maleimide moiety for selective attachment.
CAT No: CP26500
CAS No:17057-07-7
Synonyms/Alias:17057-07-7;3-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzoicacid;3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-benzoicacid;3-n-maleimidobenzoicacid;n-(3-benzoicacid)maleimide;3-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)benzoicacid;MLS003107101;CHEMBL441433;3-CARBOXYPHENYLMALEIMIDE;ZJGBFJBMTKEFNQ-UHFFFAOYSA-N;3-(2,5-dioxo-2,5-dihydropyrrol-1-yl)benzoicacid;3-(2,5-dioxopyrrol-1-yl)benzoicacid;3-(2,5-dioxo-2,5-dihydro-1h-pyrrol-1-yl)-benzoicacid;F1265-0504;Benzoicacid,3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-;3-(2,5-dioxoazolinyl)benzoicacid;NSC201626;m-Maleimidobenzoicacid;PubChem11836;AC1L3CLN;m-n-maleimidobenzoicacid;AC1Q5U3L;AC1Q72TD;AC1Q73IJ;SCHEMBL522308
3-Maleimido-benzoic acid is a benzoic acid derivative bearing a maleimide functionality, providing a well-known electrophilic alkene for selective thiol-maleimide coupling in bioconjugation workflows. Its carboxylic acid enables straightforward handling as an acid form and supports downstream derivatization or incorporation into linkers for surface immobilization and material functionalization. Researchers use this compound as a reactive small-molecule building block to introduce maleimide reactivity while maintaining a defined aromatic scaffold for conjugate construction.
1. Bioconjugation Coupling
3-Maleimido-benzoic acid is used to prepare thiol-reactive conjugation reagents for attaching biomolecules such as peptides, proteins, and antibody fragments to other functional partners. The maleimide group reacts efficiently with cysteine thiols under controlled conditions, enabling site-selective labeling strategies where a defined maleimide handle is required. The benzoic acid motif supports reagent design for linker stability and provides a convenient functional anchor for further formulation into conjugation buffers, coupling kits, or custom synthesis of bioconjugates.
2. Peptide And Protein Labeling
3-Maleimido-benzoic acid supports labeling workflows that introduce a maleimide-bearing aromatic handle for subsequent coupling to cysteine-containing peptides and proteins. In chemical biology and protein science laboratories, it is commonly used when a stable, pre-functionalized small-molecule electrophile is needed to generate conjugates with controlled stoichiometry and predictable reactivity toward thiol groups. The carboxylic acid functionality also makes it useful as a component in linker architectures that must retain an acid group for solubility tuning, purification behavior, or compatibility with downstream conjugate handling.
3. Surface Immobilization Reagents
3-Maleimido-benzoic acid is used in biomaterials and interface chemistry to build maleimide-functional surfaces and coatings that can capture thiol-bearing ligands. By leveraging the maleimide electrophile, researchers can immobilize cysteine-terminated peptides, enzyme fragments, or other thiol-functional biomolecules onto polymer films, beads, or sensor surfaces in a controlled manner. The benzoic acid group provides a practical handle for incorporating the reagent into immobilization chemistries or for designing linkers that maintain robust attachment chemistry during washing and assay preparation.
4. Linker And Crosslinker Intermediate
3-Maleimido-benzoic acid serves as a reactive intermediate for constructing defined conjugation linkers used in research-grade assay development and materials functionalization. Its maleimide moiety allows incorporation of a thiol-reactive endpoint into larger molecular designs, while the benzoic acid provides an additional functional group that can be used in linker assembly strategies. Teams developing custom conjugates for proteomics sample preparation, reagent libraries, or platform-specific immobilization often choose this compound because it offers a compact, chemically recognizable maleimide unit for modular downstream synthesis.
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