Tetronic acid

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
CAS Number	4971-56-6 (Keto form) ; 541-57-1 (Enol form);
3D model (JSmol)	Keto form: Interactive image; Enol form: Interactive image;
ChemSpider	10301432;
ECHA InfoCard	100.023.289
EC Number	208-785-3;
PubChem CID	521261;
UNII	N2B9NB89C0 (Keto form) ;
	SMILES Keto form: O=C1CC(CO1)=O; Enol form: O=C1C=C(O)CO1;
Properties
Chemical formula	C4H4O3
Molar mass	100.073 g·mol−1
Melting point	141–143 °C (286–289 °F; 414–416 K) (dec.)
Magnetic susceptibility (χ)	-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.

References

^ "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.

[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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See also

References