Citraconic anhydride

• CAS: 616-02-4
• Catalog Number: ACM-MO-616024
• Category: Main Products; Anhydride Monomers
• Molecular Weight: 112.08 g/mol
• Molecular Formula: C5H4O3
• Synonyms: 2,5-Furanedione, 3-methyl
• Canonical SMILES: CC1=CC(=O)OC1=O
• InChI: 1S/C5H4O3/c1-3-2-4(6)8-5(3)7/h2H,1H3
• InChI Key: AYKYXWQEBUNJCN-UHFFFAOYSA-N
• Boiling Point: 213-214 °C/lit.
• Melting Point: 6-10 °C (lit.)
• Density: 1.247 g/mL at 25 °C (lit.)
• Appearance: Colourless Oil
• Application: Versatile reagent used for the synthesis of maleimides, bicyclic pyrrolidines, and co- and terpolymers, as well as for the protection of N-terminal amino acids.
• Storage: Hygroscopic, Room Temperature, under inert atmosphere
• Assay: 98%
• EC Number: 210-459-0
• Features And Benefits: 1. High quality products; 2. Fast delivery; 3. Additional products can be ordered, please contact us for details
• MDL Number: MFCD00005522
• NACRES: NA.23
• Packaging: Packaging; 25, 100, 500 g in glass bottle
• PubChem ID: 24847660
• Quality Level: 200
• Refractive Index: n20/D 1.471(lit.)
• Specific Gravity: 1.245
• Vapor Density: 4 (vs air)

Case Study

Citraconic Anhydride as an Electrolyte Additive for Enhancing High-Temperature Performance of LiNi₀.₆Co₀.₂Mn₀.₂O₂/Graphite Pouch Batteries

Wang C, et al. Journal of Alloys and Compounds, 2019, 805, 757-766.

Citraconic anhydride (CAn) has been identified as an effective electrolyte additive for improving the high-temperature stability of LiNi0.6Co0.2Mn0.2O2/graphite pouch cells. Under elevated temperatures, conventional solid electrolyte interface (SEI) layers on graphite electrodes exhibit instability, leading to continuous electrolyte decomposition and capacity degradation. The inclusion of 2 wt% CAn in the electrolyte formulation facilitates the formation of a highly stable SEI film on the anode surface through reduction reactions. This CAn-derived SEI effectively suppresses the irreversible decomposition of LiPF₆ and reduces interfacial impedance, thereby enhancing the electrochemical stability of the battery. Experimental evaluations demonstrate that CAn-containing cells exhibit superior capacity retention with negligible capacity loss after 15 days of storage at 60°C. Furthermore, impedance analysis confirms that CAn mitigates the resistance buildup typically observed in pouch cells subjected to prolonged high-temperature conditions. These findings position citraconic anhydride as a promising electrolyte additive for next-generation high-energy-density lithium-ion batteries.

Citraconic Anhydride-Modified Horseradish Peroxidase for Enhanced Dye Decolorization

Liu J-Z, et al. Journal of Molecular Catalysis B: Enzymatic, 2006, 41(3-4), 81-86.

Citraconic anhydride has been employed to chemically modify horseradish peroxidase (HRP), significantly enhancing its catalytic efficiency in dye decolorization applications. The modification involved reacting HRP with citraconic anhydride in phosphate buffer (pH 7.4) at 4°C, achieving a modification degree of approximately 50%. Comparative analysis revealed that citraconic anhydride-modified HRP exhibited superior decolorization efficiencies for bromophenol blue and methyl orange, with increases of 1.8% and 12.4%, respectively, compared to native HRP.
The modified enzyme demonstrated improved catalytic performance across a wide dye concentration range (8-32 μmol L⁻¹) at 300 μmol L⁻¹ H₂O₂, aligning with industrial requirements. Additionally, kinetic analysis indicated that citraconic anhydride-modified HRP possessed greater affinity and catalytic efficiency toward the target dyes than the unmodified enzyme.

Citraconic Anhydride Used for the Synthesis of Functional Terpolymers

Kavlak S, et al. Polymer, 2010, 51(10), 2125-2132

Citraconic anhydride (CA) plays a pivotal role in the synthesis of novel functional terpolymers through complex-radical ternary polymerization with styrene (S) and vinylphosphonic acid (VPA). The terpolymerization process involves varying monomer feed ratios (40:50:10, 25:50:25, 10:50:40 mol %), conducted in a 70 wt. % DMSO solution using AIBN as an initiator at 70 °C under an inert nitrogen atmosphere. The resulting poly(CA-co-S-co-VPA) terpolymers were purified via precipitation and solvent washing, yielding well-defined materials with controlled compositions.
The incorporation of CA into these terpolymers enhances their functional diversity by introducing reactive anhydride moieties, which can facilitate further chemical modifications or crosslinking reactions. The study underscores the significance of CA as a versatile building block in the design of advanced polymeric materials with customizable functionalities.

Citraconic Anhydride Used for Stepwise Modification of Lysine Residues in Glucose Oxidase for Structural Alterations

Mossavarali S, et al. International Journal of Biological Macromolecules, 2006, 39(4-5,) 192-196.

Citraconic anhydride is a chemical reagent employed in the stepwise modification of lysine residues in proteins, such as glucose oxidase, to investigate structural changes. In the case of glucose oxidase, a dimeric enzyme with 15 lysine residues per subunit, citraconic anhydride was utilized to modify the accessible lysine residues, which are exposed on the protein's surface. The study demonstrated that this modification alters the tertiary structure of glucose oxidase, converting it to a molten globule-like form, while also inducing changes in the protein's secondary structure.
Using various spectroscopic techniques, including FTIR, far- and near-UV CD spectropolarimetry, intrinsic and extrinsic fluorescence spectroscopy, the modifications were shown to cause concentration-dependent structural changes. These changes were accompanied by a shift in the isoelectric point (pI) of the protein, as the modification of lysine residues converted positive charges to negative charges, which affected the solubility and stability of glucose oxidase. Importantly, SDS-PAGE analysis under non-reducing conditions revealed that the modification did not alter the protein's dimeric association state, although slight oligomerization occurred at higher molecular weights.