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
520-45-6 YesY
Abbreviations DHAA
ChEMBL ChEMBL284127 N
ChemSpider 10177 N
EC Number 208-293-9
Jmol interactive 3D Image
MeSH dehydroacetic+acid
PubChem 10623
UNII 2KAG279R6R YesY
Properties
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
Xn
R-phrases R22
S-phrases (S2)
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 1: Exposure would cause irritation but only minor residual injury. E.g., turpentine Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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. When used as a food additive, dehydroacetic acid is referred to using the International Numbering System for Food Additives or E number 265.

References

  1. 1 2 Merck Index, 11th Edition, 2855
  2. ↑ Raimund Miller, Claudio Abaecherli, Adel Said, Barry Jackson "Ketenes" in Ullmann's Encyclopedia of Industrial Chemistry, 2001, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a15_063
  3. ↑ Handbook of Biocide and Preservative Use, Harold William Rossmoore, p. 341 ISBN 0-7514-0212-5
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