Acetoacetic Acid
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Basic information
- CAS
541-50-4- Standard SMILES
CC(=O)CC(=O)O- InChIKey
WDJHALXBUFZDSR-UHFFFAOYSA-N- Molecular formula
- C4H6O3
- Average molar mass
- 102.09 g/mol
- Monoisotopic mass
- 102.03169405
Overview
Acetoacetic acid is a 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. It has a role as a metabolite. It is a 3-oxo fatty acid and a ketone body. It is functionally related to a butyric acid. It is a conjugate acid of an acetoacetate. It is a tautomer of a 3-hydroxy-3-butenoic acid.
Names & identifiers
- Preferred name
- Acetoacetic Acid
- IUPAC
- 3-oxobutanoic acid
- English name
- Acetoacetic Acid
- Molecular formula
- C4H6O3
- Molecular weight
- 102.09
Names & synonyms
acetoacetic acid3-oxobutanoic acid541-50-43-oxobutyric acidbeta-ketobutyric aciddiacetic acidButanoic acid, 3-oxo-3-Ketobutyric acid3-oxo-butanoic acid3-ketobutanoic acid4ZI204Y1MCCHEBI:15344
Show more names
ACETOACETATE3-oxobutanateacetoaceticaci
DTXSID00202441RefChem:5508DTXCID001249323-ketobutyrateAcetoacitic acidacetylacetic aciddiacetate3-OXO-BUTYRIC ACID
Database identifiers
- CAS
541-50-4- PubChem CID
- 96
- DTXSID
DTXSID00202441- ChEMBL
CHEMBL1230762- ChEBI
CHEBI:15344- UNII
- 4ZI204Y1MC
- Nikkaji
- J4.508J
Properties
Computed structural propertiesFilling in
- XLogP
- -0.4
- Topological polar surface area
- 54.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 2
- Heavy atoms
- 7
- Formal charge
- 0
- Complexity
- 95.1
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LipidsFatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Oxo fatty acids [FA0106]
Solubility1000 mg/mL at 20 °C
Boiling Point237.00 to 239.00 °C. @ 760.00 mm Hg
Melting Point36.5 °C
Physical DescriptionSolid
Dissociation Constants3.59 (at 0 °C)
Physicochemical properties
- Melting point
- 36 · 36-37°
- Boiling point
- 131.37 °C · 131.37°C (rough estimate)
- Density
- 1.1717 · 1.1717 (rough estimate)
- refractive index
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- ridadr
- 1759
- hazard_class
- 8
- packing_group
- III
Chemistry & industry
Pharmacology
Tissue LocationsFibroblasts
Cellular LocationsCytoplasm
Metabolite Pathways2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency
Applications
UsesIn organic syntheses.
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
DefinitionChEBI: Acetoacetic acid is a 3-oxo monocarboxylic acid that is butyric acid bearing a 3-oxo substituent. It has a role as a metabolite. It is a ketone body and a 3-oxo fatty acid. It is functionally related to a butyric acid. It is a conjugate acid of an acetoacetate. It is a tautomer of a 3-hydroxy-3-butenoic acid.
Related reactions
97 records
Compound notes
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