Tetronic acid

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

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) Y 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) Y
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.)[1]
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

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.^[6]

See also

• 5-Hydroxy-2(5H)-furanone