ChemicalBook > CAS DataBase List > 6-Maleimidocaproic acid

6-Maleimidocaproic acid

Product Name
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
Formula Weight
211.21
MOL File
55750-53-3.mol
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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)
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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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H318Causes serious eye damage

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
755842
Product name
6-Maleimidohexanoic acid
Purity
90% (GC)
Packaging
25g
Price
$224
Updated
2024/03/01
Sigma-Aldrich
Product number
63176
Product name
6-Maleimidohexanoic acid
Purity
≥98.0% (HPLC)
Packaging
1g
Price
$585
Updated
2024/03/01
TCI Chemical
Product number
M2338
Product name
6-Maleimidohexanoic Acid
Purity
>98.0%(GC)(T)
Packaging
1g
Price
$84
Updated
2024/03/01
TCI Chemical
Product number
M2338
Product name
6-Maleimidohexanoic Acid
Purity
>98.0%(GC)(T)
Packaging
5g
Price
$336
Updated
2024/03/01
Alfa Aesar
Product number
046384
Product name
6-Maleimidohexanoic acid
Packaging
5g
Price
$50
Updated
2024/03/01
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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).

6-Maleimidocaproic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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6-Maleimidocaproic acid Suppliers

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View Lastest Price from 6-Maleimidocaproic acid manufacturers

Jinan Finer Chemical Co., Ltd
Product
6-Maleimidocaproic acid 55750-53-3
Price
US $0.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20mt
Release date
2019-03-28
WUHAN FORTUNA CHEMICAL CO., LTD
Product
6-Maleimidocaproic acid 55750-53-3
Price
US $0.00/Kg/Bag
Min. Order
10g
Purity
98%min HPLC
Supply Ability
100KGS
Release date
2021-08-06
Hebei Weibang Biotechnology Co., Ltd
Product
6-Maleimidocaproic acid 55750-53-3
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100 mt
Release date
2024-11-15

55750-53-3, 6-Maleimidocaproic acidRelated Search:

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

  • 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
  • EMCA
  • EPSILON-MALEIMIDOCAPROIC ACID
  • 6-MALEIMIDOCAPROIC ACID
  • 6-MALEIMIDOHEXANOIC ACID
  • 6-MALEIMIDOCAPROIC ACID, 98+%
  • 6-Maleinimidocaproicacid
  • 6-(2,5-Dioxo-2H-pyrrol-1(5H)-yl)hexanoic acid
  • 6-MALEIMIDOHEXANOIC ACID DIHYDRATE
  • 6-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)hexanoic acid
  • 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&gt
  • 6-MaleimidocaproicAci
  • 6-(2,5-dioxopyrrol-1-yl)hexanoic acid
  • 6-maleimidylhexanoic acid
  • 6-Maleimidopropionic 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