496-64-0

Basic information

• Product Name: 3-HYDROXY-2-PYRONE
• Synonyms: 3-hydroxy-2-pyranone;3-HYDROXY-2-PYRONE;3-Hydroxy-2H-pyran-2-one;Isopyromucic acid;3-hydroxypyran-2-one;6-hydroxy-2H-pyran-2-one
• CAS NO: 496-64-0
• Molecular Formula: C₅H₄O₃
• Molecular Weight: 112.08
• Product Categories: pharmacetical
• Mol File: 496-64-0.mol
• Article Data: 9

Chemical Properties

• Melting Point: 93.8°C
• Boiling Point: 149.97°C (rough estimate)
• Flash Point: 146.7 °C
• Appearance: /
• Density: 1.2552 (rough estimate)
• Vapor Pressure: 0.000155mmHg at 25°C
• Refractive Index: 1.4390 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Methanol (Slightly)
• PKA: 8.13±0.20(Predicted)
• Water Solubility: 43.1g/L(0 oC)
• CAS DataBase Reference: 3-HYDROXY-2-PYRONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-HYDROXY-2-PYRONE(496-64-0)
• EPA Substance Registry System: 3-HYDROXY-2-PYRONE(496-64-0)

Safety Data

• Hazardous Substances Data: 496-64-0(Hazardous Substances Data)

Usage

Description

3-Hydroxy-2-pyrone, also known as 3-pyridinol, is a pyrone derivative with the molecular formula C5H4O3. It features a hydroxy group (-OH) attached to the second carbon atom of the pyrone ring. This chemical compound is commonly found in various plants and is recognized for its chelating properties, allowing it to bind to metal ions. The chelating ability, antioxidant, and anticancer properties of 3-hydroxy-2-pyrone have made it a subject of interest in medicine, agriculture, and the food industry, as well as in medicinal chemistry.

Uses

Used in Medicinal Chemistry:
3-Hydroxy-2-pyrone is used as a chelating agent for its ability to bind metal ions, which has potential applications in medicine. Its chelating properties can be utilized to treat conditions related to metal ion imbalances or to enhance the efficacy of certain drugs by binding to specific metal ions.
Used in Antioxidant Applications:
3-Hydroxy-2-pyrone is used as an antioxidant due to its ability to neutralize free radicals, thereby protecting cells from oxidative damage. This application is particularly relevant in the prevention and treatment of various diseases associated with oxidative stress.
Used in Anticancer Applications:
3-Hydroxy-2-pyrone is used as an anticancer agent for its potential to inhibit the growth of cancer cells. Its mechanism of action may involve the disruption of cellular processes that promote cancer cell proliferation and survival.
Used in Agriculture:
3-Hydroxy-2-pyrone is used in agriculture as a chelating agent to improve the uptake of nutrients by plants, particularly micronutrients that are essential for plant growth but are less available in the soil due to their interaction with other soil components.
Used in the Food Industry:
3-Hydroxy-2-pyrone is used in the food industry for its potential as a natural preservative. Its antioxidant properties can help to extend the shelf life of food products by preventing oxidation, which is a common cause of food spoilage.

InChI:InChI=1/C5H4O3/c6-4-2-1-3-8-5(4)7/h1-3,6H

Upstream product

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• 93905-59-0 3-hydroxy-2-oxo-2H-pyran-6-carboxylic acid 

Downstream Products

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Relevant articles and documents

Degradation of ascorbic acid in ethanolic solutions

Ascorbic acid occurs naturally in many wine-making fruits. The industry also uses ascorbic acid as an antioxidant and color stabilizer in the making of alcoholic beverages including white wine, wine cooler, alcopop, and fruit liqueur. However, the degradation of ascorbic acid itself may cause browning and the deterioration of color quality. This study was aimed to monitor the degradation of ascorbic acid, the formation of degradation products, and the browning in storage of ascorbic acid containing 0-40% (v/v) ethanolic solutions buffered at pH 3.2 as models of alcoholic beverages. The results show that ascorbic acid degradation in the ethanolic solutions during storage follows first-order reaction, that the degradation and browning rates increase with the increase of ethanol concentration, that the activation energy for the degradation of ascorbic acid is in the range 10.35-23.10 (kcal/mol), that 3-hydroxy-2-pyrone is an indicator and a major product of ascorbic acid degradation, and that aerobic degradation pathway dominants over anaerobic pathway in ascorbic acid degradation in ethanolic solutions.

Total synthesis of the Cephalotaxus norditerpenoids (±)-cephanolides A-D

Concise syntheses of the Cephalotaxus norditerpenoids cephanolides A-D (8-14 steps from commercial material) using a common late-stage synthetic intermediate are described. The success of our approach rested on an early decision to apply chemical network analysis to identify the strategic bonds that needed to be forged, as well as the efficient construction of the carbon framework through iterative Csp2-Csp3 cross-coupling, followed by an intramolecular inverse-demand Diels-Alder cycloaddition. Strategic late-stage oxidations facilitated access to all congeners of the benzenoid cephanolides isolated to date.

Enantioselective Total Synthesis of (+)-Iso-A82775C, a Proposed Biosynthetic Precursor of Chloropupukeananin

(+)-Iso-A82775C is a proposed biosynthetic precursor of the chloropupukeananin family and an important intermediate for related natural products. The first enantioselective total synthesis of (+)-iso-A82775C (18 steps, 2.2% overall yield) toward the eventual biomimetic total synthesis of chloropupukeananin is described. The key steps are (1) the enantioselective Diels-Alder reaction of 4-bromo-3-hydroxy-2-pyrone with methyl 2-chloroacrylate using cinchonine as an organocatalyst and (2) the anti-selective Cu-mediated SN2′ reaction to afford the axially chiral vinylallene moiety.