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| | 6-Maleimidocaproic acid Basic information |
| | 6-Maleimidocaproic acid Chemical 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 | | 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) |
| 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 |
| | 6-Maleimidocaproic acid Usage And Synthesis |
| 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 | Succinic anhydride-->Maleic anhydride-->(Z)-6-(3-Carboxyacrylamido)hexanoic acid-->6-Aminocaproic acid | | Preparation Products | MC-Val-Cit-PAB-->Mc-Val-Cit-PABC-PNP-->McMMAE-->CarbaMic acid, [5-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)pentyl]-, 1,1-diMethylethyl ester-->1H-Pyrrole-1-hexanoic acid, 2,5-dihydro-2,5-dioxo-, 2-[(1,1-diMethylethoxy)carbonyl]hydrazide |
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