1,6-Bismaleimidoethane
Product Information
Molecular Formula
C14H16N2O4
Molecular Weight
276.29
Description
1,6-Bismaleimidoethane is a crosslinking reagent used in biomedical research, specifically in protein and peptide studies. It assists in the structure-function analysis of proteins and modification of biomolecules by creating covalent bonds between thiols.
Synonyms
1,6-Bismaleimidoethane; 1,6-bis-(Maleimide)hexane
IUPAC Name
1-[6-(2,5-dioxopyrrol-1-yl)hexyl]pyrrole-2,5-dione
SMILES
C1=CC(=O)N(C1=O)CCCCCCN2C(=O)C=CC2=O
InChI
InChI=1S/C14H16N2O4/c17-11-5-6-12(18)15(11)9-3-1-2-4-10-16-13(19)7-8-14(16)20/h5-8H,1-4,9-10H2
InChI Key
PYVHLZLQVWXBDZ-UHFFFAOYSA-N
Boiling Point
419.2°C (rough estimate)
Melting Point
144 °C
Purity
>97.0%(LC)(N)
Density
1.1933 (rough estimate)
Appearance
Off-White to Pale Yellow Solid
Application
A sulfhydryl reactive homobifunctional crosslinking reagent. Under mild conditions, will permit irreversible cross-linking of sulfhydral containing compounds at a pH range of 6.5 to 7.5.
Spacer Arm: 16.1 Angstroms
Spacer Arm: 16.1 Angstroms
Refractive Index
1.5500 (estimate)
Safety Information
Hazards
H302:
Harmful if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Harmful if swallowed.
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
Precautionary Statement
P264:
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312+P330:
IF SWALLOWED:
Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Wash thoroughly after handling.
P270:
Do not eat, drink or smoke when using this product.
P280:
Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312+P330:
IF SWALLOWED:
Call a POISON CENTER or doctor/physician if you feel unwell.
Rinse mouth.
P337+P313:
If eye irritation persists:
Get medical advice/attention.
P501:
Dispose of contents/container in accordance with local/regional/national/international regulations.
Computed Properties
XLogP3
0.2
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
7
Exact Mass
276.11100700 g/mol
Monoisotopic Mass
276.11100700 g/mol
Topological Polar Surface Area
74.8Ų
Heavy Atom Count
20
Formal Charge
0
Complexity
425
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-114133704-A | Resin composition, prepreg and application | 2021-12-31 |
| CN-112898919-A | Novel low-VOC (volatile organic compound) heat vulcanization adhesive and use method thereof | 2021-02-05 |
| CN-112812711-A | High-reactivity metal-rubber heat-vulcanization adhesive and using method thereof | 2021-01-25 |
| JP-2021080457-A | Thermosetting resin compositions, prepregs, laminates, printed wiring boards and semiconductor packages | 2021-01-13 |
| JP-6981522-B1 | Thermosetting resin composition and its use | 2020-12-15 |
| CN-112731807-A | Balance point containment control method of complex dynamic saturated network model | 2020-12-11 |
| CN-111965940-A | Positive photosensitive polyimide resin composition, method for producing resin composition, and use thereof | 2020-08-31 |
| JP-2022039583-A | Resin composition, resin film with carrier using it, resin substrate, prepreg, metal-clad laminate, printed wiring board, and semiconductor device | 2020-08-28 |
| JP-2022039594-A | Resin composition, resin film with carrier using it, resin substrate, prepreg, metal-clad laminate, printed wiring board, and semiconductor device | 2020-08-28 |
| WO-2022032293-A2 | Treatment of diseases related to colony-stimulating factor 1 receptor dysfunction using trem2 agonists | 2020-08-05 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 22573538 | 2012-09-01 | Pharmaceutical aspects of the recombinant human serum albumin dimer: structural characteristics, biological properties, and medical applications | Journal of pharmaceutical sciences |
| 22363641 | 2012-01-01 | Ligand-induced movements of inner transmembrane helices of Glut1 revealed by chemical cross-linking of di-cysteine mutants | PloS one |
| 20855459 | 2010-12-01 | Superior plasma retention of a cross-linked human serum albumin dimer in nephrotic rats as a new type of plasma expander | Drug metabolism and disposition: the biological fate of chemicals |
| 20590134 | 2010-08-03 | The V510D suppressor mutation stabilizes DeltaF508-CFTR at the cell surface | Biochemistry |
| 20360986 | 2010-03-30 | Use of human cancer cell lines mitochondria to explore the mechanisms of BH3 peptides and ABT-737-induced mitochondrial membrane permeabilization | PloS one |
| 19583260 | 2009-12-10 | Synthesis and in vitro evaluation of N-substituted maleimide derivatives as selective monoglyceride lipase inhibitors | Journal of medicinal chemistry |
| 18471993 | 2008-07-11 | Design, synthesis, and biophysical properties of a helical Abeta1-42 analog: Inhibition of fibrillogenesis and cytotoxicity | Biochemical and biophysical research communications |
| 16554295 | 2006-05-19 | Cross-linking of C-terminal residues of phospholamban to the Ca2+ pump of cardiac sarcoplasmic reticulum to probe spatial and functional interactions within the transmembrane domain | The Journal of biological chemistry |
| 15644311 | 2005-03-18 | Role of leucine 31 of phospholamban in structural and functional interactions with the Ca2+ pump of cardiac sarcoplasmic reticulum | The Journal of biological chemistry |
| 15582322 | 2004-12-07 | Inhibition of ErbB2 causes mitochondrial dysfunction in cardiomyocytes: implications for herceptin-induced cardiomyopathy | Journal of the American College of Cardiology |
