Tetronic acid is a

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one ele ...

, classified as a γ-lactone, with the molecular formula C₄H₄O₃. It interconverts between keto and enol

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hyd ...

s: : Many

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...

s such as

ascorbic acid Vitamin C (also known as ascorbic acid and ascorbate) is a water-soluble vitamin found in citrus and other fruits and vegetables, also sold as a dietary supplement and as a topical 'serum' ingredient to treat melasma (dark pigment spots) a ...

(vitamin C), penicillic acid,

pulvinic acid Pulvinic acids are natural chemical pigments found in some lichens, derived biosynthetically from the aromatic amino acids phenylalanine and tyrosine, via dimerization and oxidative ring-cleavage of arylpyruvic acids, a process that also produces ...

s, and abyssomicins possess the β-keto-γ-butyrolactone motif of tetronic acid. In

organic synthesis Organic synthesis is a special branch of chemical synthesis and is concerned with the intentional construction of organic compounds. Organic molecules are often more complex than inorganic compounds, and their synthesis has developed into one o ...

, it is used as a precursor for other substituted and ring-fused

furan Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans. Furan is a colorless, flammable, highly ...

s and

butenolide Butenolides are a class of lactones with a four-carbon heterocyclic ring structure.Joule JA, Mills K. (2000). Heterocyclic Chemistry 4th ed. Blackwell Science Publishing: Oxford, UK They are sometimes considered oxidized derivatives of furan. Th ...

s. It is also forms the structural core of a class of pesticides, known as tetronic acid insecticides, which includes

spirodiclofen Spirodiclofen is an acaricide and insecticide used in agriculture to control mites and San Jose scale. In the United States, it is used on citrus, grapes, pome fruit, stone fruit, and tree nut crops. Spirodiclofen belongs to the tetronic acid cl ...

and spiromesifen.

References

{{reflist Furanones

See also

References