58626-38-3

Basic information

• Product Name: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester
• Synonyms: MBS;3-MALEIMIDOBENZOIC ACID N-HYDROXYSUCCINIMIDE ESTER;3-MALEIMIDOBENZOIC ACID N-SUCCINIMIDYL ESTER;3-(2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-yl)benzoic acid 2,5-dioxopyrrolidine-1-yl ester;3-(2,5-Dioxo-3-pyrroline-1-yl)benzoic acid succinimidyl ester;3-(Maleimide-N-yl)benzoic acid succinimidyl ester;3-[(2,5-Dioxo-2,5-dihydro-1H-pyrrole)-1-yl]benzoic acid 2,5-dioxo-1-pyrrolidinyl ester;Succinimidylmaleimidobenzoate
• CAS NO: 58626-38-3
• Molecular Formula: C₁₅H₁₀N₂O₆
• Molecular Weight: 314.25
• EINECS: 261-368-8
• Product Categories: Cross Linking Reagents,Maleimide Derivatives;MTS & Sulfhydryl Active Reagents;Heterobifunctional Crosslinker;heteroXlink;Nitric Oxide Reagents;N-Substituted Maleimides;N-Substituted Maleimides, Succinimides & Phthalimides;N-Substituted Succinimides;Cross Linking Reagents;Maleimide Derivatives
• Mol File: 58626-38-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 175-177 °C(lit.)
• Boiling Point: 524.5 °C at 760 mmHg
• Flash Point: 271 °C
• Appearance: /crystalline
• Density: 1.59 g/cm³
• Vapor Pressure: 4.29E-11mmHg at 25°C
• Refractive Index: 1.678
• Storage Temp.: −20°C
• Solubility: ethyl acetate or DMF: ≤20 mg/mL may require addition
• PKA: -2.63±0.20(Predicted)
• Sensitive: Moisture & Light Sensitive
• BRN: 1505254
• CAS DataBase Reference: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester(58626-38-3)
• EPA Substance Registry System: 3-Maleimidobenzoic acid N-hydroxysuccinimide ester(58626-38-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 58626-38-3(Hazardous Substances Data)

Usage

Description

MBS is a heterobifunction crosslinker that contains a maleimide group which is reactive towards sulfhydryls and an NHS ester, useful for targeting amine groups.

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 58626-38-3 differently. You can refer to the following data:
1. 3-Maleimidobenzoic acid N-hydroxysuccinimide ester is a heterobifunctional coupling reagent useful for forming enzyme immunoconjugates. The reactive groups are the NHS ester and maeimide.
2. N-Succinimidyl 3-maleimidobenzoate is useful for forming enzyme immunoconjugates. It has a 9.9 Angstrom spacer arm. Heterobifunctional crosslinking reagent reactive toward primary amine and sulfhydryl. Useful for preparation of enzyme immunoconjugates and hapten carrier molecule conjugates

Biochem/physiol Actions

3-Maleimidobenzoic acid N-hydroxysuccinimide is used as a fixative for the preservation of pollen tube F-actin distribution. It imposes less damage when used on pollen tubes.

InChI:InChI=1/C15H10N2O6/c18-11-4-5-12(19)16(11)10-3-1-2-9(8-10)15(22)23-17-13(20)6-7-14(17)21/h1-5,8H,6-7H2

Upstream product

• 108-31-6 maleic anhydride 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 99-05-8 meta-aminobenzoic acid 
• 17057-07-7 3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-benzoic acid 
• 36847-92-4 3-[[(2Z)-3-carboxy-1-oxo-2-propen-1-yl]amino]benzoic acid 
• 5672-89-9 N-trifluoroacetoxy succinimide 

Downstream Products

• 103003-30-1 cholest-5-en-3β-yl 6-(m-maleimidobenzamido)hexyl ether 

Relevant articles and documents

Preparation method of 3-maleimide succinimide benzoate

The invention discloses a preparation method of 3-maleimide succinimide benzoate. The preparation method is characterized by including following steps: step 1, preparing a solution by dissolving m-aminobenzoic acid into DMF; step 2, adding maleic anhydride into the DMF solution with the m-aminobenzoic acid; step 3, adding N-hydroxysucciminide and a proper condensation agent into a reaction system;step 4, performing aftertreatment to obtain a crude product, recrystallizing through a proper solvent, and refining to obtain a pure product. No matter purity and melting point or yield data of the pure product are satisfactory. The preparation method is simple, convenient, short in production period, high in safety, suitable for industrial production, easy-to-get in raw material and low in cost.

Facile synthesis of reagents containing a terminal maleimido ligand linked to an active ester

Condensation of ω-amino acids with maleic anhydride to yield maleamino acids and subsequent esterification with N-hydroxysuccinimide, 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine, or pentafluorophenol to give the corresponding esters in a one pot procedure are described. The reagents can be isolated and purified without chromatography in 7-55% yields.

Preparation and Characterization of Hetero-bifunctional Cross-linking Reagents for Protein Modifications

Ten aromatic and aliphatic cross-linking reagents of hetero-bifunctional type were synthesized as part of a search for useful reagents of this type.All of the reagents possess two selectively reactive groups a maleimide group which can combine with a thiol group via its double bond and an N-Hydroxysuccinimidyl ester (one of the most hydrophilic active esters), which can react with an ammmine group.It was found that the active esters of the reagents tested were mostly more reactive with lysine than with leucine, and acylated amino acids more rapidly at pH 8.0 than at pH 7.0.It was also found that the stability of the maleimide group in the compounds tested depends largely upon the pH of the buffer used.The most stable pH was 5.0-6.0.To use one of the present compounds as a cross-linker, the crystalline reagent should be dissolved in tetrahydrofuran of dioxane and the solution used for cross-linking.The acylation step should be carried out first with thiol addition to the maleimide group as the second step.The optimum pH of the buffer used for the first step is slightly basic.The reaction time should be limited to less than 1 hr.When the first step is over, the pH of the reaction mixture should be changed to 5.0-6.0.Keywords---cross-linker; hetero-bifunctional reagent; reactivity of N-hydroxy-succinimidyl ester; stability of maleimide residue; N-(maleimidobenzoyloxy)succinimide derivative; N-(maleimidoalkyloxy)succinimide derivative