1219-33-6

Basic information

• Product Name: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid
• Synonyms: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid;4-oxo-5-(phenylMethoxy)-4H-Pyran-2-carboxylic acid;4H-Pyran-2-carboxylic acid, 4-oxo-5-(phenylmethoxy)-
• CAS NO: 1219-33-6
• Molecular Formula: C₁₃H₁₀O₅
• Molecular Weight: 246.2155
• EINECS: 200-258-5
• Mol File: 1219-33-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 196-198℃ (methanol )
• Boiling Point: 501.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 1.67±0.20(Predicted)
• CAS DataBase Reference: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid(1219-33-6)
• EPA Substance Registry System: 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid(1219-33-6)

Safety Data

• Hazardous Substances Data: 1219-33-6(Hazardous Substances Data)

Usage

General Description

5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid is a chemical compound that belongs to the group of pyran carboxylic acids. It is characterized by the presence of a benzene ring attached to an oxygen atom, as well as a carboxylic acid group and a pyran ring with an oxo (ketone) group. 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid has potential applications in medicinal chemistry, particularly in the development of pharmaceutical drugs. It may also have uses in organic synthesis and as a building block for the creation of other chemical compounds. The structure and properties of 5-(benzyloxy)-4-oxo-4H-pyran-2-carboxylic acid make it an interesting and potentially valuable substance for various scientific and industrial purposes.

Upstream product

• 15771-06-9 5-benzyloxy-2-hydroxymethyl-4H-pyran-4-one 
• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 61049-67-0 3-Benzyloxy-4-pyrone 
• 742026-59-1 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid 
• 119736-19-5 2-Pyridinecarboxylic acid, 1,4-dihydro-1-methyl-4-oxo-5-(phenylmethoxy)- 
• 499-78-5 comenic acid 
• 1333329-01-3 3-hydroxy-3'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333328-92-9 3-hydroxy-4'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333329-88-6 3'-fluoro-3-hydroxy-4'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333328-90-7 3-hydroxy-6'-phenyl-4H-1,2'-bipyridin-4-one 
• 1333328-89-4 3-hydroxy-1-(2-phenylpyrimidin-4-yl)pyridin-4(1H)-one 
• 1333329-16-0 4'-(3,4-dichlorophenyl)-3-hydroxy-4H-1,2'-bipyridin-4-one 

Relevant articles and documents

Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity

A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.

A Convenient Preparation of Carboxy-γ-pyrone Derivatives: Meconic Acid and Comenic Acid

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5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method

The present invention discloses a 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method comprising the following steps: adding kojic acid, benzyl chloride and methanol benzyl chloride into a reaction vessel, and heating for reflux reaction for 16 to 18 hours; distilling under reduced pressure, evaporating the solvent to dryness, and cooling to room temperature; adding methanol and water, stirring, washing, filtering and drying to obtain an intermediate; and adding the intermediate and water into the reaction vessel, reducing the temperature to 0 DEG C to -10 DEG C, adding sodium periodate, controlling the temperature to be not higher than 5 DEG C, then adding dropwise a proper amount of water, stirring for 5-15 minutes, heating to 12 DEG C-22 DEG C, stirring for reaction for 2.5 to 3.5 hours, extracting with ethyl acetate, layering, drying, filtering and drying to obtain white solid 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid. The new 5-benzyloxy-4-oxo-4H-pyran-2-carboxylic acid preparation method is provided, does not produce large amounts of chromium-containing waste water, prevents severe environmental pollution, and can achieve industrial production.