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| Names | |
|---|---|
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Preferred IUPAC name
3-Acetyl-2-hydroxy-6-methyl-4H-pyran-4-one | |
| Other names
Biocide 470F
Methylacetopyronone | |
| Identifiers | |
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3D model (JSmol)
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| Abbreviations | DHAA |
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.541 |
| EC Number |
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| E number | E265 (preservatives) |
| MeSH | dehydroacetic+acid |
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PubChem CID
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| UNII | |
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CompTox Dashboard (EPA)
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| Properties | |
| C8H8O4 | |
| Molar mass | 168.148 g·mol−1 |
| Appearance | White crystals |
| Melting point | 109 °C; 228 °F; 382 K |
| Boiling point | 270 °C; 518 °F; 543 K |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302 | |
| P264, P270, P301+P312, P330, P501 | |
| NFPA 704 (fire diamond) | |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dehydroacetic acid is an organic compound which has several industrial applications. The compound is classified as a pyrone derivative. It presents as an odorless, colorless to white crystalline powder, almost insoluble in water and moderately soluble in most organic solvents.
Preparation
It is prepared by the base-catalysed dimerization of diketene. Commonly used organic bases include imidazole, DABCO, and pyridine.
Uses
Industrially, dehydroacetic acid has several uses which include the following:
- 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.
- as a food preservative to prevent pickle bloating in squash and strawberries. When used as a food additive, dehydroacetic acid is referred to using the International Numbering System for Food Additives or E number 265.
- as a plasticizer in synthetic resins.
- as an antienzyme in toothpastes.
- as a precursor for dimethyl-4-pyridones. The compounds are synthesized when dehydroacetic acid is exposed to aqueous solutions containing primary amines.