acetonylacetone

Also 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.

In the Vinony graph

Vinony's link graph records 231 inbound references to acetonylacetone, and connects out to International Standard Book Number, mass density and digital object identifier.

It sits within the topics Chembox having GHS data, Diketones and ECHA InfoCard ID from Wikidata.

Vinony links it to 17 Wikipedia language editions.

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 Å²
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

Sources (4)

via Wikidata · CC0

~1 min read

Encyclopedic overview

5 sections

Contents

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.