487-66-1

Basic information

• Product Name: 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid
• Synonyms: 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid;2-(2-Carboxyethyl)-3-methylmaleic Anhydride;3-(4-Methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoic acid;2-propionic-3-methylmaleic anhydride;3-(4-methyl-2,5-dioxo-2,5-dihydrofuran-3-yl)propanoic acid (Related Reference)
• CAS NO: 487-66-1
• Molecular Formula: C₈H₈O₅
• Molecular Weight: 184.14612
• Mol File: 487-66-1.mol

Chemical Properties

• Melting Point: 97.0 to 101.0 °C
• Boiling Point: 391°C at 760 mmHg
• Flash Point: 164.7°C
• Appearance: /
• Density: 1.408g/cm³
• Vapor Pressure: 3.33E-07mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 4.31±0.10(Predicted)
• CAS DataBase Reference: 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid(487-66-1)
• EPA Substance Registry System: 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid(487-66-1)

Safety Data

• Hazardous Substances Data: 487-66-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid is used as an intermediate in the synthesis of various pharmaceuticals for its potential medicinal properties. Its antioxidant and anti-inflammatory characteristics contribute to the development of drugs that can address a range of health conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid is utilized as a key component in the formulation of agrochemicals. Its role in these products is crucial for enhancing crop protection and improving agricultural yields.
Used in Research and Development:
2,5-Dihydro-4-methyl-2,5-dioxo-3-furanpropanoic Acid is employed as a research compound for exploring its chemical properties and potential applications in various scientific fields. Its unique structure and reactivity make it valuable for advancing knowledge in chemistry and related disciplines.

InChI:InChI=1/C8H8O5/c1-4-5(2-3-6(9)10)8(12)13-7(4)11/h2-3H2,1H3,(H,9,10)

Upstream product

• 493-90-3 mesoporphyrin IX 
• 14459-29-1 hematoporphyrin 
• 5965-53-7 diethyl 2-ketoglutarate 
• 766-39-2 2,3-Dimethylmaleic anhydride 
• 13192-04-6 dimethyl 2-ketoglutarate 
• 3699-66-9 ethyl 2-diethoxyphosphorylpropionate 
• 496919-84-7 C₁₂H₁₈O₆ 
• 154222-94-3 3-pentene-1,3,4-tricarboxylic acid 1,3,4-triethyl ester 
• 577-53-7 C₈H₁₀O₆ 
• 98453-81-7 2-(bromomethyl)-3-methyl maleic anhydrate 
• 347406-12-6 3-[2,2-Bis(ethoxycarbonyl)]ethyl-4-methyl-2,5-furandione 
• 635-65-4 bilirubin 
• 859950-65-5 4-hydroxy-pentane-1,3,4-tricarboxylic acid 
• 1501-06-0 diethyl 2-acetylglutarate 

Downstream Products

• 110-15-6 succinic acid 
• 487-65-0 3-(4-methyl-2,5-dioxo-2,5-dihydro-pyrrol-3-yl)-propionic acid 

Relevant articles and documents

Synthetic Studies on Tautomycin Synthesis of 2,3-Disubstituted Maleic Anhydride Segment

The 2,3-disubstituted maleic anhydride segment of tautomycin has been synthesized in optically active form.Oxidation of 3,4-disubstituted furan employing singlet oxygen completes the construction of the maleic anhydride moiety.Esterification of the maleic anhydride segment without protecting anhydride moiety resulted in the successful coupling reaction with fragment derived from tautomycin.

Acidic pH-responsive siRNA conjugate for reversible carrier stability and accelerated endosomal escape with reduced IFNα-associated immune response

An siRNA conjugate is based on an acid-labile maleic acid amide linkage for programmed transfer of siRNA from the endosome to the cytosol and siRNA release in the cell interior. The procedure relies on reversible stability in response to endosomal acidic

A medusa-like β-cyclodextrin with 1-methyl-2-(2'-carboxyethyl) maleic anhydrides, a potential carrier for pH-sensitive drug delivery

We developed a new pH-sensitive drug delivery carrier based on β-cyclodextrin (β-CD) and 1-methyl-2-(2'-carboxyethyl) maleic anhydrides (MCM). The primary hydroxyl groups of β-CD were successfully attached to MCM residues to produce a medusa-like β-CD-MCM. The MCM residue was conjugated with cephradine (CP) with high efficiency (>90%). More importantly, β-CD-MCM-CP responded to the small pH drop from 7.4 to 5.5 and released greater than 80% of the drugs within 0.5h at pH 5.5. In addition, the inclusion complex between β-CD-MCM-CP and the adamantane derivative was formed by simple mixing to show the possibility of introducing multi-functionality. Based on these results, β-CD-MCM can target weakly acidic tissues or organelles, such as tumours, inflammatory tissues, abscesses or endosomes, and be easily modified with various functional moieties, such as ligands for cell binding or penetration, enabling more efficient and specific drug delivery.

REVERSING THE UNDESIRABLE pH-PROFILE OF DOXORUBICIN VIA ACTIVATION OF A DISUBSTITUTED MALEAMIC ACID PRODRUG AT TUMOR ACIDITY

A pre-prodrug, comprising a drug, e.g., doxorubicin, which has off-target toxicity (e.g., cardiotoxicity) with respect to its antineoplastic activity, and an amine functionality of the drug incorporated into a disubstituted maleimide (DMI). The pre-prodrug may be linked to a targeting or de-targeting agent or a polar modulator, e.g., charged ligand, amino acid, peptide, etc., to increase therapeutic index. The pre-prodrug is hydrolyzed to the prodrug, having a disubstituted maleamic acid (DMA). A polar modulator such as glutamic acid prevents cellular uptake of the prodrug, but not the doxorubicin drug released from the prodrug after dissociation. The prodrug is pH sensitive, and below pH 7.0, tends to cleave to form free drug and cyclized maleic anhydride. Tumor environments tend to be more acidic, e.g., pH 6.8, than cardiac tissue, e.g., pH 7.4, and therefore the heart is spared while the drug is selectively released within a tumor.

Nano clustering enzyme with hypoxia activation prodrug and preparation method and application of enzyme

The invention provides a nano clustering enzyme with a hypoxia activation prodrug. The nano clustering enzyme has capacity of targeted tumor hunger and hypoxia activation and is a mode for cancer treatment through cooperation of a chemotherapy and metabolic treatment. An adopted cross-linking agent material polyethylene glycol-b-poly(2-hydroxyethyl methacrylate)segmented copolymer modified by 2-carboxyethyl cellulose-3-methyl maleic anhydride has the acidity response characteristic and can have specificity in tumor targeting breaking. The nano clustering enzyme takes a bovine serum albumin-hypoxia activation drug as a shell, the bovine serum albumin has good biocompatibility and stability so that the nano clustering enzyme can stably exist in the blood, the blood circulation time is prolonged, and the tumor gathering effect is improved. Through the shell, advanced exposure of the enzyme in a core can be avoided, and the toxicity to the normal tissue is lowered. The nano clustering enzyme has good stability and dispersity and is beneficial to biological application.

Reversing the undesirable pH-profile of doxorubicin: Via activation of a di-substituted maleamic acid prodrug at tumor acidity

The acid-labile behavior of di-substituted maleamic acid (DMA) and its equilibrium with di-substituted maleimide (DMI) are exploited to build an ultra acid-sensitive, small molecule prodrug that can be activated by tumor extracellular pH (pHe) in the range of 6.5-6.9. Such a DMA prodrug reversed the unfavorable pH-profile of doxorubicin (Dox), which may improve its therapeutic window.

Galactose cluster-pharmacokinetic modulator targeting moiety for siRNA

The present invention is directed compositions for targeted delivery of RNA interference (RNAi) polynucleotides to cell in vivo. The pharmacokinetic modulator improve in vivo targeting compared to the targeting ligand alone. Targeting ligand-pharmacokinet

COMPOSITIONS FOR TARGETED DELIVERY OF SIRNA

The present invention is directed compositions for targeted delivery of RNA interference (RNAi) polynucleotides to hepatocytes in vivo. Targeted RNAi polynucleotides are administered together with co-targeted delivery polymers. Delivery polymers provide m

A pH responsive cyclodextrin derivative, a preparation method therof and a pH responsive conjugate of the cyclodextrin derivative and a drug

The present invention relates to a pH-responsive cyclodextrin derivative, a preparation method thereof, and a pH-responsive conjugate of the pH-responsive cyclodextrin derivative and a drug, and more specifically, to a cyclodextrin derivative having a novel structure, a preparation method thereof, and a pH-responsive conjugate of the pH-responsive cyclodextrin derivative and a drug. The cyclodextrin derivative has a novel structure formed by a covalent bond between a maleic anhydride derivative and a cyclodextrin or a cyclodextrin derivative, in which a residue of the maleic anhydride derivative bonds to a primary hydroxyl group of cyclodextrin or a terminal functional group, such as NH_2, N_3, or amino acid, of a cyclodextrin derivative to produce a pH-responsive cyclodextrin derivative.(AA) Cyclodextrin(BB) Maleic acid derivative(CC) Amine group (-NH_2)-containing drugCOPYRIGHT KIPO 2016

Comparison of pH-sensitive degradability of maleic acid amide derivatives

We synthesized five maleic acid amide derivatives (maleic, citraconic, cis-aconitic, 2-(2′-carboxyethyl) maleic, 1-methyl-2-(2′- carboxyethyl) maleic acid amide), and compared their degradability for the future development of pH-sensitive biomaterials with tailored kinetics of the release of drugs, the change of charge density, and the degradation of scaffolds. The degradation kinetics was highly dependent upon the substituents on the cis-double bond. Among the maleic acid amide derivatives, 2-(2′-carboxyethyl) maleic acid amide with one carboxyethyl and one hydrogen substituent showed appropriate degradability at weakly acidic pH, and the additional carboxyl group can be used as a pH-sensitive linker.