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6-Maleimidocaproic acid

CAS No.
55750-53-3
Chemical Name:
6-Maleimidocaproic acid
Synonyms
6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid;EMCA;6-MALEIMIDOHEXANOIC ACID;6-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)hexanoic acid;MalHex;Maleimide-(CH2)5-COOH;6-MaleimidocaproicAci;Mal-(CH2)5-COOH (EMCA);6-MALEIMIDOCAPROIC ACID;6-MaleiMidocapronic acid
CBNumber:
CB6300928
Molecular Formula:
C10H13NO4
Molecular Weight:
211.21
MDL Number:
MFCD00043140
MOL File:
55750-53-3.mol
MSDS File:
SDS
Last updated:2023-10-19 14:01:02

6-Maleimidocaproic acid 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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS05,GHS07
Signal word  Danger
Hazard statements  H315-H318-H335
Precautionary statements  P280-P302+P352-P305+P351+P338+P310
Hazard Codes  Xi
Risk Statements  36/37/38-41-37/38
Safety Statements  26-36-39
WGK Germany  3
10-21
HS Code  29251900
NFPA 704
0
2 0

6-Maleimidocaproic acid price More Price(44)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 755842 6-Maleimidohexanoic acid 90% (GC) 55750-53-3 25g $224 2024-03-01 Buy
Sigma-Aldrich 63176 6-Maleimidohexanoic acid ≥98.0% (HPLC) 55750-53-3 1g $585 2024-03-01 Buy
TCI Chemical M2338 6-Maleimidohexanoic Acid >98.0%(GC)(T) 55750-53-3 1g $84 2024-03-01 Buy
TCI Chemical M2338 6-Maleimidohexanoic Acid >98.0%(GC)(T) 55750-53-3 5g $336 2024-03-01 Buy
Alfa Aesar 046384 6-Maleimidohexanoic acid 55750-53-3 5g $50 2024-03-01 Buy
Product number Packaging Price Buy
755842 25g $224 Buy
63176 1g $585 Buy
M2338 1g $84 Buy
M2338 5g $336 Buy
046384 5g $50 Buy

6-Maleimidocaproic acid Chemical Properties,Uses,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).
6-Maleimidocaproic acid

108-30-5
60-32-2
55750-53-3
Synthesis of 6-Maleimidocaproic acid from Succinic anhydride and 6-Aminocaproic acid
Global( 329)Suppliers
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Shanghai Gubang New Materail Technology Co. LTD
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Hebei Guanlang Biotechnology Co., Ltd.
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View Lastest Price from 6-Maleimidocaproic acid manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
6-Maleimidocaproic acid pictures 2024-03-19 6-Maleimidocaproic acid
55750-53-3
US $0.00 / kg 1kg 99% 20mt Jinan Finer Chemical Co., Ltd
6-Maleimidocaproic acid pictures 2023-09-06 6-Maleimidocaproic acid
55750-53-3
US $0.00-0.00 / KG 1KG 99% 500000kg Hebei Guanlang Biotechnology Co., Ltd.
6-Maleimidocaproic acid pictures 2023-08-24 6-Maleimidocaproic acid
55750-53-3
US $0.00 / KG 1KG 99% 50000KG/month Hebei Mojin Biotechnology Co., Ltd

6-Maleimidocaproic acid Spectrum

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 ε-MaleiMidohexanoic Acid 6-MaleiMidocapronic acid EPSILON-MALEIMIDOCAPROIC ACID 6-MALEIMIDOCAPROIC ACID 6-MALEIMIDOCAPROIC ACID, 98+% 6-Maleinimidocaproicacid 6-MALEIMIDOHEXANOIC ACID DIHYDRATE 6-Maleimidocaproic acid N-(5-Carboxypentyl)maleimide 6-Maleimide hexanoic acid EMCA 6-Maleimidocaproic acid 6-Maleimidohexanoic acid 90% (GC) 1H-Pyrrole-1-hexanoicacid, 2,5-dihydro-2,5-dioxo- MalHex Maleimide-(CH2)5-COOH 6-MaleimidohexanoicAcid> 6-MaleimidocaproicAci 6-(2,5-dioxopyrrol-1-yl)hexanoic acid EMCA 6-MALEIMIDOHEXANOIC ACID 6-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)hexanoic acid 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid 6-maleimidylhexanoic acid 55750-53-3 Probe for thiol groups (SH-groups) in membrane proteins Chiral Building Blocks Asymmetric Synthesis Carboxylic Acids Organic Building Blocks Maleimide Derivatives Cross Linking Reagents MTS & Sulfhydryl Active Reagents ADCs ADC Linker