Structure via PubChem · Public domain (PubChem)
acetonylacetone
Sign in to saveAlso known as CH3COCH2CH2COCH3, NSC 7621, alpha,beta-diacetylethane, Acetonyl acetone, 2,5-Diketohexane, 1,2-Diacetylethane, 2,5-Hexadione, hexane-2,5-dione
2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. In humans, it is a toxic metabolite of hexane and of 2-hexanone.
Chemical data
- Formula
- C6H10O2
- Molecular weight
- 114.14 g/mol
- IUPAC name
- hexane-2,5-dione
- SMILES
- CC(=O)CCC(=O)C
- InChIKey
- OJVAMHKKJGICOG-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 34.1 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
657 papers- 2,5-hexanedione-induced testicular injury.Annual review of pharmacology and toxicology · 2003
- Dimercaptols of acetonylacetone.Journal of the American Chemical Society · 1948
- The noncoincidence phenomenon of acetonylacetone C[double bond, length as m-dash]O stretching in a binary mixture and the aggregation-induced split theory.RSC advances · 2020
- Detection and disaggregation of amyloid fibrils by luminescent amphiphilic platinum(II) complexes.Dalton transactions (Cambridge, England : 2003) · 2024
- Real-time monitoring of the reaction between aniline and acetonylacetone using extractive electorspray ionization tandem mass spectrometry.Scientific reports · 2019
via PubMed
Wikidata facts
- Mass
- 114.068
Show 5 more facts
- chemical formula
- C₆H₁₀O₂
- melting point
- -6
- canonical SMILES
- CC(=O)CCC(=O)C
- found in taxon
- Magnolia obovata
- Commons category
- Hexane-2,5-dione
via Wikidata · CC0
~1 min read
Encyclopedic overview
5 sectionsContents
- Symptoms of poisoning
- Mechanism of action
- Synthesis
- Uses
- References
2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. In humans, it is a toxic metabolite of hexane and of 2-hexanone.
==Symptoms of poisoning== The chronic toxicity of hexane is attributed to hexane-2,5-dione. The symptoms are tingling and cramps in the arms and legs, followed by general muscular weakness. In severe cases, atrophy of the skeletal muscles is observed, along with a loss of coordination and vision problems.
Excerpted from Wikipedia’s “acetonylacetone” article, available under the CC BY-SA 4.0 licence.