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6-Maleimidocaproic acid

CAS No.55750-53-3
Chemical Name:6-Maleimidocaproic acid
CBNumber:CB6300928
Molecular Formula:C10H13NO4
Formula Weight:211.21
MOL File:55750-53-3.mol

6-Maleimidocaproic acid Property

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
InChI InChI=1S/C10H13NO4/c12-8-5-6-9(13)11(8)7-3-1-2-4-10(14)15/h5-6H,1-4,7H2,(H,14,15)
InChIKey WOJKKJKETHYEAC-UHFFFAOYSA-N
SMILES N1(CCCCCC(O)=O)C(=O)C=CC1=O
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)
UNSPSC Code 12352005
NACRES NA.25

Safety

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

NFPA 704:

	0
2		0

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H315-H318-H335
Precautionary statements P280-P302+P352-P305+P351+P338+P310

6-Maleimidocaproic acid Price More Price(4)

Brand: Sigma-Aldrich(India)
Product number: 755842
Product name : 6-Maleimidohexanoic acid
Purity: 90% (GC)
Packaging: 25G
Price: ₹11983.28
Updated: 2022/06/14
Buy: Buy

Brand: Sigma-Aldrich(India)
Product number: 63176
Product name : 6-Maleimidohexanoic acid
Purity: ≥98.0% (HPLC)
Packaging: 1G
Price: ₹32312.63
Updated: 2022/06/14
Buy: Buy

Brand: TCI Chemicals (India)
Product number: M2338
Product name : 6-Maleimidohexanoic Acid
Purity: min. 98.0 %
Packaging: 1G
Price: ₹2800
Updated: 2022/05/26
Buy: Buy

Brand: TCI Chemicals (India)
Product number: M2338
Product name : 6-Maleimidohexanoic Acid
Purity: min. 98.0 %
Packaging: 5G
Price: ₹13000
Updated: 2022/05/26
Buy: Buy

6-Maleimidocaproic acid Chemical Properties,Usage,Production

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).