Dehydroacetic acid

Dehydroacetic acid^[1]

Names
Preferred IUPAC name 3-Acetyl-2-hydroxy-6-methyl-4H-pyran-4-one
Other names Biocide 470F Methylacetopyronone
Identifiers
Abbreviations	DHAA
CAS Registry Number	520-45-6 Y
ChEMBL	ChEMBL284127 N
ChemSpider	10177 N
EC number	208-293-9
InChI InChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,11H,1-2H3 N Key: JEQRBTDTEKWZBW-UHFFFAOYSA-N N
Jmol-3D images	Image
MeSH	dehydroacetic+acid
PubChem	10623
SMILES CC(=O)C1=C(O)OC(C)=CC1=O
UNII	2KAG279R6R Y
Properties
Molecular formula	C8H8O4
Molar mass	168.15 g·mol−1
Appearance	White crystals
Melting point	109 °C; 228 °F; 382 K
Boiling point	270 °C; 518 °F; 543 K
Hazards
EU Index	607-163-00-2
EU classification	Xn
R-phrases	R22
S-phrases	(S2)
NFPA 704	1 1 0
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Dehydroacetic acid is an organic compound. The compound is classified as a pyrone derivative and is used mostly as a fungicide and bactericide. The sodium salt, sodium dehydroacetate, is often used in place of dehydroacetic acid because of its greater solubility in water. It is prepared by the base-catalysed dimerization of diketene.^[2]

Applications

Industrially, it is also used as a plasticizer in synthetic resins.^[1] It is used to reduce pickle bloating as a preservative for squash and strawberries.^[3] Also used in antienzyme toothpastes. Clinical tests show little to no evidence regarding the ingredient's toxicity and potential for irritation.^[4]

References