Zymonic acid

Zymonic acid
Names
	IUPAC name 4-hydroxy-2-methyl-5-oxofuran-2-carboxylic acid
	Other names 2,5-Dihydro-4-hydroxy-2-methyl-5-oxo-2-furancarboxylic acid; 4-hydroxy-2-methyl-5-oxo-2,5-dihydrofuran-2-carboxylic acid;
Identifiers
CAS Number	24891-71-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:172309;
ChemSpider	35013332;
PubChem CID	71436380;
CompTox Dashboard (EPA)	DTXSID701187301;
	InChI InChI=1S/C6H6O5/c1-6(5(9)10)2-3(7)4(8)11-6/h2,7H,1H3,(H,9,10) Key: FMOWGHRAYUFXIG-UHFFFAOYSA-N;
	SMILES CC1(C=C(C(=O)O1)O)C(=O)O;
Properties
Chemical formula	C6H6O5
Molar mass	158.109 g·mol−1
Appearance	white solid
Density	1.523 g/cm3
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Zymonic acid is an organic compound with the empirical formula C₆H₆O₅. It is the product from the condensation of a two molecules of pyruvic acid:^[1]

2 CH₃C(O)CO₂H → (O=C)(HOC)(HC)OC(CH₃)(CO₂H) + H₂O

The molecule is an unsaturated furanone, as established by X-ray crystallography.^[2] In aqueous solution, zymonic acid reversibly converts to a variety of derivatives including ring-opened and cyclic hydrates. ^[3]

References

^ Klingler, Franz Dietrich; Ebertz, Wolfgang (2000). "Oxocarboxylic Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a18_313. ISBN 978-3-527-30385-4.
^ Heger, Dominik; Eugene, Alexis J.; Parkin, Sean R.; Guzman, Marcelo I. (2019). "Crystal structure of zymonic acid and a redetermination of its precursor, pyruvic acid". Acta Crystallographica Section E. 75 (6): 858–862. doi:10.1107/S2056989019007072. PMC 6658982. PMID 31391982.
^ Perkins, Russell J.; Shoemaker, Richard K.; Carpenter, Barry K.; Vaida, Veronica (2016). "Chemical Equilibria and Kinetics in Aqueous Solutions of Zymonic Acid". The Journal of Physical Chemistry A. 120 (51): 10096–10107. doi:10.1021/acs.jpca.6b10526. PMID 27991786.

[1] Klingler, Franz Dietrich; Ebertz, Wolfgang (2000). "Oxocarboxylic Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a18_313. ISBN 978-3-527-30385-4.

[2] Heger, Dominik; Eugene, Alexis J.; Parkin, Sean R.; Guzman, Marcelo I. (2019). "Crystal structure of zymonic acid and a redetermination of its precursor, pyruvic acid". Acta Crystallographica Section E. 75 (6): 858–862. doi:10.1107/S2056989019007072. PMC 6658982. PMID 31391982.

[3] Perkins, Russell J.; Shoemaker, Richard K.; Carpenter, Barry K.; Vaida, Veronica (2016). "Chemical Equilibria and Kinetics in Aqueous Solutions of Zymonic Acid". The Journal of Physical Chemistry A. 120 (51): 10096–10107. doi:10.1021/acs.jpca.6b10526. PMID 27991786.

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