6-Maleimidocaproic acid

Synonym(s):MCA;6-Maleimidocaproic acid;Maleimidocaproic acid;N-Maleoyl-6-aminocaproic acid;2,5-Dihydro-2,5-dioxo-1H-pyrrole-1-hexanoic acid

CAS NO.：55750-53-3
Empirical Formula: C10H13NO4
Molecular Weight: 211.21
MDL number: MFCD00043140
EINECS: 611-311-1
SAFETY DATA SHEET (SDS)
Update Date: 2023-10-19 14:01:02

What is 6-Maleimidocaproic acid?

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.

The Uses of 6-Maleimidocaproic acid

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.

What are the applications of 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).

Properties of 6-Maleimidocaproic acid

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
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 for 6-Maleimidocaproic acid

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H318:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water.