Tetronic acid

Chemical compound From Wikipedia, the free encyclopedia

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

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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 Edit this at Wikidata
EC Number
  • 208-785-3
UNII
  • InChI=1S/C4H4O3/c5-3-1-4(6)7-2-3/h1-2H2
    Key: JCGNDDUYTRNOFT-UHFFFAOYSA-N
  • 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).
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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.[6]

See also

References

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