Tetronic acid is a chemical compound, classified as a γ-lactone, with the molecular formula C4H4O3.
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| Preferred IUPAC name
4-Hydroxyfuran-2(5H)-one | |
Other names
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3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.023.289 |
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PubChem CID
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| Properties | |
| C4H4O3 | |
| Molar mass | 100.073 g·mol−1 |
| Melting point | 141–143 °C (286–289 °F; 414–416 K) (dec.)[1] |
| -52.5·10−6 cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It interconverts between keto and enol tautomers:[2]
Many natural products such as ascorbic acid (vitamin C), penicillic acid, pulvinic acids, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid.[3]
In organic synthesis, it is used as a precursor for other substituted and ring-fused furans and butenolides.[4][5] It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes spirodiclofen and spiromesifen.
See also
editReferences
edit- ^ "2,4(3H,5H)-Furandione". Sigma-Aldrich.
- ^ Abdou, Moaz M.; El-Saeed, Rasha A.; Abozeid, Mohamed A.; Elattar, Khaled M.; Zaki, E.G.; Barakat, Y.; Ibrahim, V.; Fathy, Mahmoud; Amine, M.; Bondock, Samir (2015). "Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions". Arabian Journal of Chemistry. 12 (4): 464–475. doi:10.1016/j.arabjc.2015.11.004.
- ^ Georgiadis, Dimitris; Zografos, Alexandros (2006). "Synthetic Strategies towards Naturally Occurring Tetronic Acids". Synthesis. 2006 (19): 3157. doi:10.1055/s-2006-950202.
- ^ "Tetronic acid". Alfa Aesar.
- ^ Schmidt, Diane Grob; Seemuth, Paul D.; Zimmer, Hans (1983). "Substituted .gamma.-butyrolactones. Part 31. 2,4(3H,5H)-Furandione: Heteroannulations with aromatic o-amino carbonyl compounds and condensations with some vic-polyones". The Journal of Organic Chemistry. 48 (11): 1914. doi:10.1021/jo00159a029.