Acetoacetic Acid

HCID 96CAS 541-50-4

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Basic information

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 properties

XLogP: -0.4
Topological polar surface area: 54.4 Å²
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

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: 1.454 · 1.4540 (estimate)
pka: 3.58 · 3.58(at 18℃)
PH: 3.4 · 3.4(1 mM solution);2.83(10 mM solution);2.3(100 mM solution)
Water Solubility: 2 O, · sol H2O, alcohol
LogP: -0.467 · -0.467 (est)
FDA UNII: 4 ZI204Y1MC · 4ZI204Y1MC
RIDADR: 1759 · 1759
HazardClass: 8 · 8
PackingGroup: III

Safety & regulation

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

Ethyl acetoacetate

Downstream products

7-Hydroxycoumarin-4-acetic acid 2-Acetyl-isonicotinonitrile Propanal, 2-oxo-, 1-oxime, (1E)-

Suppliers50 total

陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]

湖北万得化工有限公司15377098680 15377098680 · [email protected]

Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]

武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]

广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]

Additional notes · 1 item

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.