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
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)
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
- Storage Class
- 11 - Combustible Solids
- Hazard Classifications
- Skin Irrit. 2
STOT SE 3
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.
N-Bromosuccinimide Price
- Product number
- 755842
- Product name
- 6-Maleimidohexanoic acid
- Purity
- 90% (GC)
- Packaging
- 25g
- Price
- $232
- Updated
- 2025/07/31
- Product number
- 63176
- Product name
- 6-Maleimidohexanoic acid
- Purity
- ≥98.0% (HPLC)
- Packaging
- 1g
- Price
- $602
- Updated
- 2025/07/31
- Product number
- M2338
- Product name
- 6-Maleimidohexanoic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 1g
- Price
- $76
- Updated
- 2025/07/31
- Product number
- M2338
- Product name
- 6-Maleimidohexanoic Acid
- Purity
- >98.0%(GC)(T)
- Packaging
- 5g
- Price
- $302
- Updated
- 2025/07/31
- Product number
- M137950
- Product name
- 6-MaleimidocaproicAcid
- Packaging
- 25g
- Price
- $465
- Updated
- 2021/12/16
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).
References
[1] Patent: CN107789630, 2018, A. Location in patent: Paragraph 0061; 0062; 0063
[2] Patent: CN108743968, 2018, A. Location in patent: Paragraph 0004; 0005; 0006
[3] Patent: WO2015/95223, 2015, A2. Location in patent: Page/Page column 67
[4] Patent: WO2016/90050, 2016, A1. Location in patent: Page/Page column 61-62
[5] Patent: WO2016/90038, 2016, A1. Location in patent: Page/Page column 123
6-Maleimidocaproic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from 6-Maleimidocaproic acid manufacturers
- Product
- 6-Maleimidocaproic acid 55750-53-3
- Price
- US $0.00-0.00/KG
- Min. Order
- 1KG
- Purity
- 98.0%
- Supply Ability
- 10000KGS
- Release date
- 2025-07-07
- 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
- 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