Name: 5-Maleimidovaleric acid
Brand: BOC Sciences
Price: -- USD
Availability: MadeToOrder

Synonyms

5-(2,5-Dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoic acid; 1H-Pyrrole-1-pentanoic acid, 2,5-dihydro-2,5-dioxo-; 5-(2,5-Dioxopyrrol-1-yl)pentanoic acid

IUPAC Name

5-(2,5-dioxopyrrol-1-yl)pentanoic acid

Canonical SMILES

C1=CC(=O)N(C1=O)CCCCC(=O)O

InChI

InChI=1S/C9H11NO4/c11-7-4-5-8(12)10(7)6-2-1-3-9(13)14/h4-5H,1-3,6H2,(H,13,14)

InChIKey

ACVAAFHNDGTZLL-UHFFFAOYSA-N

Density

1.3±0.1 g/cm3

Solubility

10 mm in DMSO

Flash Point

196.2±24.0 °C

Index Of Refraction

1.544

PSA

74.68000

Vapor Pressure

0.0±2.0 mmHg at 25°C

Appearance

Solid

Shelf Life

-20°C 3 years powder; -80°C 2 years in solvent

Shipping

Room temperature

Storage

Store at -5°C,keep in dry and avoid sunlight.

Boiling Point

400.7±28.0 °C at 760 mmHg

Form

Solid

5-Maleimidovaleric acid, a versatile compound in the scientific community, has four prominent applications, each contributing significantly to various fields of research and development. This compound’s unique chemical structure allows it to be used extensively in bioconjugation techniques. Bioconjugation is a process where two biomolecules are chemically linked, often to enhance the properties of medical and biochemical research substances. The maleimide group in 5-Maleimidovaleric acid reacts with thiol groups in proteins or peptides, forming stable thioether bonds. This reaction is highly specific, allowing researchers to attach imaging agents, drugs, or other functional groups to target molecules precisely. The application in bioconjugation significantly advances targeted delivery systems, making treatments more effective and reducing side effects.

Another critical application of 5-Maleimidovaleric acid is in the development of polymer materials. It serves as a cross-linking agent in the formation of hydrogels, which are networks of polymer chains that can retain water. These hydrogels have widespread applications in biomedical fields, such as wound dressings, drug delivery systems, and tissue engineering. The presence of the maleimide functional group ensures that 5-Maleimidovaleric acid can create strong covalent bonds, enhancing the mechanical stability and durability of the hydrogels. Consequently, these improved hydrogel materials are more effective in their applications, providing better outcomes in medical treatments and research.

In the realm of organic synthesis, 5-Maleimidovaleric acid is invaluable for creating complex molecules. Its ability to participate in Michael addition reactions, where it acts as an electron-deficient Michael acceptor, opens pathways for synthesizing various compounds. Researchers leverage this property to construct new materials and chemicals with desired properties, including pharmaceuticals, agricultural chemicals, and advanced materials. The specificity and reactivity of 5-Maleimidovaleric acid make it a vital tool in the synthesis process, enabling the creation of compounds that might be challenging to produce through other methods. This broadens the scope of what’s possible in chemical research and industrial applications.

Lastly, 5-Maleimidovaleric acid plays a significant role in the field of proteomics and genomics. In these fields, it is used for labeling and detecting biomolecules. The specificity of the maleimide-thiol reaction allows for precise modification of proteins and nucleotides, facilitating the study of protein functions, interactions, and locations within the cell. By attaching fluorescent dyes, affinity tags, or other detectable markers to proteins and DNA, researchers can track and analyze biological processes with high precision. This application enhances our understanding of cellular mechanisms and disease pathways, paving the way for innovative therapeutic strategies and diagnostic tools. The ability of 5-Maleimidovaleric acid to aid in these complex studies underscores its importance in advancing modern biological research.