![]() | |
Names | |
---|---|
IUPAC name
Pyran-2-one | |
Other names
α-Pyrone | |
Identifiers | |
| |
3D model (JSmol) |
|
ChEBI | |
ChemSpider |
|
ECHA InfoCard | 100.007.264 ![]() |
PubChem CID |
|
CompTox Dashboard (EPA) |
|
| |
| |
Properties | |
C5H4O2 | |
Molar mass | 96.08 |
Density | 1.197 g/mL |
Boiling point | 102 to 103 °C (216 to 217 °F; 375 to 376 K) at 20 mmHg |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Pyrone (α-pyroneorpyran-2-one) is an unsaturated cyclic chemical compound with the molecular formula C5H4O2. It is isomeric with 4-pyrone.
2-Pyrone is used in organic synthesis as a building block for more complex chemical structures because it may participate in a variety of cycloaddition reactions to form bicyclic lactones. For example, it readily undergoes Diels-Alder reactions with alkynes producing, upon loss of carbon dioxide, substituted benzenes.[2] The Gogte Synthesis (1938) is a method for the alkylation of certain pyrones with acid chlorides.[citation needed]
The most common natural products containing a 2-pyrone are the bufanolides and kavalactones. Oxovitisin A, a pyranoanthocyanin found in wine, also contains a 2-pyrone element.
6-amyl-α-pyrone (6PP) is a class of 2-pyrone, found in animal foods and heated beef <https://pubchem.ncbi.nlm.nih.gov/compound/6-Pentyl-2H-pyran-2-one#section=Top>. Due to its good organoleptic properties with cocnut aroma, it is used as flavor enhancer in the food industry. Biologically, it is produced by Trichoderma species via solid state fermentation <Aline de Souza Ramos; Sorele Batista Fiaux; Selma Gomes Ferreira Leite; Production of 6-pentyl-α-pyrone by trichoderma harzianum in solid-state fermentation, doi.org/10.1590/S1517-83822008000400022>. Alam et al. explored 6PP to generate 2-none-4-one and 4-nonanone via decarboxylation and hydrogenation reaction <Md. Imteyaz Alam, Shelaka Gupta, Ashish Bohre, Ejaz Ahmad, Tuhin S. Khan, Basudeb Saha, M. Ali Haider; Development of 6-amyl-α-pyrone as a potential biomass-derived platform molecule; Green Chem., 2016, 18, 6431-6435; DOI: 10.1039/C6GC02528E>.