Tetronic acid explained

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

It interconverts between keto and enol tautomers:^[1]

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.^[2]

In organic synthesis, it is used as a precursor for other substituted and ring-fused furans and butenolides.^{[3] [4]} It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes spirodiclofen and spiromesifen.

See also

• 5-Hydroxy-2(5H)-furanone

Notes and References

1. 10.1016/j.arabjc.2015.11.004. Advancements in tetronic acid chemistry. Part 1: Synthesis and reactions. Arabian Journal of Chemistry. 2015. 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. 12. 4. 464–475. free.
2. 10.1055/s-2006-950202. Synthetic Strategies towards Naturally Occurring Tetronic Acids. Synthesis. 2006. 19. 3157. 2006. Georgiadis. Dimitris. Zografos. Alexandros.
3. Web site: Tetronic acid. Alfa Aesar .
4. 10.1021/jo00159a029. 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. 1983. Schmidt. Diane Grob. Seemuth. Paul D.. Zimmer. Hans.