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6-Maleimidocaproic acid

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6-Maleimidocaproic acid Basic information

Product Name:
6-Maleimidocaproic acid
Synonyms:
  • N-MALEOYL-6-AMINO-CAPROIC ACID
  • N-EPSILON-MALEIMIDOCAPROIC ACID
  • N-(5-CARBOXYPENTYL)MALEIMIDE
  • 6-Maleimidocaproic acid, N-(5-Carboxypentyl)maleimide, N-Maleoyl-6-aminocaproic acid
  • 6-Maleimidohexanoic acid,6-Maleimidocaproic acid, N-(5-Carboxypentyl)maleimide, N-Maleoyl-6-aminocaproic acid
  • Mal-(CH2)5-COOH (EMCA)
  • 2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic Acid
  • N-(5-Carboxy-n-pentyl)MaleiMide
CAS:
55750-53-3
MF:
C10H13NO4
MW:
211.21
EINECS:
611-311-1
Product Categories:
  • Maleimide Derivatives
  • Cross Linking Reagents
  • MTS & Sulfhydryl Active Reagents
  • ADCs
  • ADC Linker
Mol File:
55750-53-3.mol
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6-Maleimidocaproic acid Chemical Properties

Melting point:
86-91 °C
Boiling point:
407.3±28.0 °C(Predicted)
Density 
1.285±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO (Slightly), Ethyl Acetate (Slightly)
form 
Powder
pka
4.74±0.10(Predicted)
color 
White to pale yellow
Water Solubility 
Soluble in water, methanol, ethanol, dimethyl sulfoxide. Insoluble in ether.
Sensitive 
Moisture Sensitive
BRN 
1532405
InChIKey
WOJKKJKETHYEAC-UHFFFAOYSA-N
CAS DataBase Reference
55750-53-3(CAS DataBase Reference)
EPA Substance Registry System
1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo- (55750-53-3)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38-41-37/38
Safety Statements 
26-36-39
WGK Germany 
3
10-21
HS Code 
29251900

MSDS

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6-Maleimidocaproic acid Usage And Synthesis

Description

6-Maleimidocaproic acid contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Chemical Properties

White to yellow solid, powder, crystals or crystaline powder.

Uses

6-Maleimidohexanoic acid is used as a probe for introducing maleimides groups into biomolecules and active pharmaceutical ingredients. Further, it is used with N-hydroxysuccinimide ester as a bifunctional cross-linking reagent. In addition to this, it acts as a probe for thiol groups in membrane proteins.

Definition

ChEBI: 6-Maleimidocaproic acid is a medium-chain fatty acid. It contains a maleimide group and a terminal carboxylic acid. The terminal carboxylic acid can react with primary amine groups in the presence of activators (e.g. EDC, or HATU) to form a stable amide bond. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Application

6-Maleimidocaproic acid is a sulfhydryl reactive heterobifunctional crosslinking reagent. It can be widely used probe for introducing maleimides groups into biomolecules. A probe for thiol groups in proteins. Spacer Arm: 9.4 Angstroms. Probe for thiol groups (SH-groups) in membrane proteins.

Synthesis

Maleic anhydride (29.4 g, 0.3 mol) and 6-aminocaproic acid (39.35 g, 0.3 mol) were refluxed in glacial acetic acid (900 mL) for 16 h. Acetic anhydride (30.6 g, 0.3 mol) was added dropwise over a period of 2 hand reflux was continued for 1 h. The acetic acid was removed under vacuum at 70 °C to yield yellow syrup which solidified. The material was chromatographed over silica using dichloromethane-methanol-acetic acid (100:5:1) affording a crystalline solid (6-Maleimidocaproic acid).

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