Date published: 2025-11-22

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N-Hydroxymaleimide (CAS 4814-74-8)

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Alternate Names:
N-Hydroxymaleamine; 1-Hydroxy-2,5-dihydro-1H-pyrrole-2,5-dione
CAS Number:
4814-74-8
Molecular Weight:
113.07
Molecular Formula:
C4H3NO3
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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N-Hydroxymaleimide, part of the pyrrole family, is a naturally occurring organic compound present in various plants and fungi. Its diverse presence has spurred extensive research across medicine, biochemistry, and scientific domains. It demonstrates potential as an antioxidant by effectively neutralizing free radicals and as a cytochrome P450 enzyme inhibitor, offering insights into drug metabolism processes.


N-Hydroxymaleimide (CAS 4814-74-8) References

  1. Solid-state conjugation of proteins with hydrophobic compounds in non-denaturing conditions. I. Acylation of proteins by dansyl proline using a polymeric N-hydroxysuccinimide ester.  |  Gershkovich, AA., et al. 2000. J Biochem Biophys Methods. 45: 183-91. PMID: 10989134
  2. A New Approach for Oxygenation Using Nitric Oxide under the Influence of N-Hydroxyphthalimide.  |  Eikawa, M., et al. 1999. J Org Chem. 64: 4676-4679. PMID: 11674538
  3. Coupling of contact sensitizers to thiol groups is a key event for the activation of monocytes and monocyte-derived dendritic cells.  |  Becker, D., et al. 2003. J Invest Dermatol. 120: 233-8. PMID: 12542528
  4. N-hydroxyimides as efficient ligands for the copper-catalyzed N-arylation of pyrrole, imidazole, and indole.  |  Ma, HC. and Jiang, XZ. 2007. J Org Chem. 72: 8943-6. PMID: 17935350
  5. Differential inhibition of human T-lymphocyte activation by maleimide probes.  |  Freed, BM., et al. 1986. Cell Immunol. 101: 181-94. PMID: 2943414
  6. Selectfluor-induced C(sp2)-O coupling reaction of N-substituted anilines with hydroxylamine derivatives.  |  Sun, B., et al. 2018. Org Biomol Chem. 16: 6017-6024. PMID: 30087978
  7. Thermodynamic and Kinetic Study of Diels-Alder Reaction between Furfuryl Alcohol and N-Hydroxymaleimides-An Assessment for Materials Application.  |  Carneiro de Oliveira, J., et al. 2020. Molecules. 25: PMID: 31936088
  8. Design of Bowl-Shaped N-Hydroxyimide Derivatives as New Organoradical Catalysts for Site-Selective C(sp3)-H Bond Functionalization Reactions.  |  Kato, T. and Maruoka, K. 2020. Angew Chem Int Ed Engl. 59: 14261-14264. PMID: 32488943
  9. Chromogenic Chemodosimeter Based on Capped Silica Particles to Detect Spermine and Spermidine.  |  Barros, M., et al. 2021. Nanomaterials (Basel). 11: PMID: 33806899
  10. Low levels of ionic mercury modulate protein tyrosine phosphorylation in lymphocytes.  |  Rosenspire, AJ., et al. 1998. Int J Immunopharmacol. 20: 697-707. PMID: 9877281
  11. Synthesis and polymerization of t-BOC protected maleimide monomers: N-(t-butyloxycarbonyloxy) maleimide and N-[p-(t-butyloxycarbonyloxy) phenyl]-maleimide  |  Ahn, K. D., Koo, D. I., & Willson, C. G. 1995. Polymer. 36(13): 2621-2628.
  12. Effect of pH on the drug release rate from a new polymer–drug conjugate system  |  Kenawy, E. R., Abdel‐Hay, F., El‐Newehy, M., & Ottenbrite, R. M. 2008. Polymer International. 57(1): 85-91.
  13. Polyolefin fibers with chemically fixed active ester for the solid phase synthesis of an amide derivative  |  Nagata, K., Kato, S., Jyo, A., Tamada, M., & Katakai, A. 2009. Reactive and Functional Polymers. 69(1): 9-13.

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

N-Hydroxymaleimide, 1 g

sc-208038
1 g
$205.00