6-Maleimidocaproic acid

Bezeichnung:6-Maleimidocaproic acid

CAS-Nr55750-53-3

Englisch Name:6-Maleimidocaproic acid

CBNumberCB6300928

SummenformelC10H13NO4

Molgewicht211.21

MOL-Datei55750-53-3.mol

6-Maleimidocaproic acid physikalisch-chemischer Eigenschaften

Schmelzpunkt	86-91 °C
Siedepunkt	407.3±28.0 °C(Predicted)
Dichte	1.285±0.06 g/cm3(Predicted)
storage temp.	2-8°C
Löslichkeit	DMSO (Slightly), Ethyl Acetate (Slightly)
Aggregatzustand	Powder
pka	4.74±0.10(Predicted)
Farbe	White to pale yellow
Wasserlöslichkeit	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 Datenbank	55750-53-3(CAS DataBase Reference)
EPA chemische Informationen	1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo- (55750-53-3)

Sicherheit

Kennzeichnung gefährlicher	Xi
R-Sätze:	36/37/38-41-37/38
S-Sätze:	26-36-39
WGK Germany	3
F	10-21
HS Code	29251900
Speicherklasse	11 - Combustible Solids
Hazard Classifications	Skin Irrit. 2 STOT SE 3

Gefahreninformationscode (GHS)

6-Maleimidocaproic acid Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Beschreibung
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.
Chemische Eigenschaften
White to yellow solid, powder, crystals or crystaline powder.
Verwenden
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.
Synthese
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).
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte

6-Maleimidocaproic acid Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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