DEHYDROACETIC ACID (CHEM005305)

Record Information
Version1.0
Creation Date2016-05-19 02:00:23 UTC
Update Date2026-08-25 04:22:53 UTC
Accession NumberCHEM005305
Identification
Common NameDEHYDROACETIC ACID
ClassSmall Molecule
Description
A pyran-2,4-dione substituted at position 3 by an acetyl group and at position 6 by a methyl group. A fungicide and bactericide it is used primarily in processed fruit and vegetables.
Contaminant Sources
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Biocide 470FChEBI
MethylacetopyrononeChEBI
DehydroacetateGenerator
DHASMeSH
Dehydroacetic acid, zinc ion (1-)MeSH
DHA-SMeSH
Dehydroacetic acid, potassium ion (1-)MeSH
Sodium dehydroacetateMeSH
Dehydroacetic acid ion (1-)MeSH
Dehydroacetic acid, sodium ion (1-)MeSH
Dihydroxyacetone sulfateMeSH
Dehydroacetic acid, sodium monohydrate ion (1-)MeSH
e265ChEMBL
Chemical FormulaC8H8O4
Average Molecular Mass168.148 g/mol
Monoisotopic Mass168.042 g/mol
CAS Registry Number520-45-6
IUPAC Name3-acetyl-6-methyl-3,4-dihydro-2H-pyran-2,4-dione
Traditional Namedehydroacetic acid
SMILESCC(=O)C1C(=O)OC(C)=CC1=O
InChI IdentifierInChI=1S/C8H8O4/c1-4-3-6(10)7(5(2)9)8(11)12-4/h3,7H,1-2H3
InChI KeyPGRHXDWITVMQBC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentDihydropyranones
Alternative Parents
Substituents
  • Dihydropyranone
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Enol ester
  • Cyclic ketone
  • Lactone
  • Ketone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility23.2 g/LALOGPS
logP0.11ALOGPS
logP0.44ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)1.09ChemAxon
pKa (Strongest Basic)-6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area60.44 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity41.33 m³·mol⁻¹ChemAxon
Polarizability15.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkDehydroacetic_acid
Chemspider IDNot Available
ChEBI ID137426
PubChem Compound ID122903
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18960990
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23790920
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=25813167
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=4030634
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=6885696
7.