Tetronic acid
Names
Preferred IUPAC name
4-Hydroxyfuran-2(5H)-one
Other names
  • 3H,5H-Furan-2,4-dione
  • 3-Hydroxybutenolide
  • 3-Hydroxy-2-buteno-4-lactone
  • 3-Oxo-γ-butyrolactone
  • Tetrahydrofuran-2,4-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.023.289
EC Number
  • 208-785-3
UNII
  • Keto form: O=C1CC(CO1)=O
  • Enol form: O=C1C=C(O)CO1
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).
Infobox references

Tetronic acid is a chemical compound, classified as a γ-lactone, with the molecular formula C4H4O3.

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

References

  1. ↑ "2,4(3H,5H)-Furandione". Sigma-Aldrich.
  2. ↑ 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.
  3. ↑ Georgiadis, Dimitris; Zografos, Alexandros (2006). "Synthetic Strategies towards Naturally Occurring Tetronic Acids". Synthesis. 2006 (19): 3157. doi:10.1055/s-2006-950202.
  4. ↑ "Tetronic acid". Alfa Aesar.
  5. ↑ 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.
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