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)

pka

4.74±0.10(Predicted)

form 

Powder

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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-41-37/38

Safety Statements 

26-36-39

WGK Germany 

3

F 

10-21

HS Code 

29251900

MSDS

• Language:English Provider:SigmaAldrich

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).

6-Maleimidocaproic acid(55750-53-3)Related Product Information

• Citric acid
• N,N'-1,3-Phenylene bismaleimide
• Folic acid
• N-Benzylmaleimide
• Bismaleimide
• Ethyl 2-(Chlorosulfonyl)acetate
• Hyaluronic acid
• O-Phthalimide
• N-Phenylmaleimide
• Hexanoic acid
• N-Ethylmaleimide
• Maleimide
• Succinimide
• Ascoric Acid
• Polyamideimide
• SMCC crosslinker
• N-Succinimidyl 6-maleimidohexanoate
• DIALIFOS