ContaminantDB: 2,5-Hexanedione

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2014-09-08 02:39:15 UTC

Update Date

2026-04-16 21:17:41 UTC

Accession Number

CHEM003599

Identification

Common Name

2,5-Hexanedione

Class

Small Molecule

Description

2,5-Hexanedione is an aliphatic diketone. It is a prototypical neurotoxicants metabolite of hexane and of 2-hexanone that presumably act through the formation of protein adducts. It appears that the neurotoxicity of 2,5-hexanedione resides in its gamma-diketone structure since 2,3-, 2,4-hexanedione and 2,6-heptanedione are not neurotoxic, while 2,5-heptanedione and 3,6-octanedione and other gamma-diketones are neurotoxic. 2,5-Hexanedione reacts with critical lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking between two n-hexane-modified proteins. The resulting denaturation of proteins perturbs axonal transport and function and causes damage to nerve cells.

Contaminant Sources

HPV EPA Chemicals
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Industrial/Workplace Toxin
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2-Diacetylethane	ChEBI
2,5-Diketohexane	ChEBI
2,5-Hexadione	ChEBI
Acetonyl acetone	ChEBI
Acetonylacetone	ChEBI
alpha,beta-Diacetylethane	ChEBI
CH3COCH2CH2COCH3	ChEBI
Hexane-2,5-dione	ChEBI
NSC 7621	ChEBI
a,b-Diacetylethane	Generator
Α,β-diacetylethane	Generator
alpha, beta-Diacetylethane	HMDB
Diacetonyl	HMDB
2,5-Dioxohexane	HMDB
Acetone, acetonyl	HMDB

Chemical Formula

C₆H₁₀O₂

Average Molecular Mass

114.142 g/mol

Monoisotopic Mass

114.068 g/mol

CAS Registry Number

110-13-4

IUPAC Name

hexane-2,5-dione

Traditional Name

2,5-hexanedione

SMILES

CC(=O)CCC(C)=O

InChI Identifier

InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3

InChI Key

OJVAMHKKJGICOG-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

methyl ketone (CHEBI:85014 )
diketone (CHEBI:85014 )
Oxygenated hydrocarbons (LMFA12000081 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Actin Filament
Cell surface
Cytoplasm
Cytoskeleton
Cytosol
Endoplasmic reticulum
Extracellular
Intermediate Filament
Microtubule
Mitochondrion
Nerve Fiber
Perinuclear region
Plasma Membrane
Synaptic Vesicle
Tubulin

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Apoptosis	Not Available	map04210
Cell cycle	Not Available	map04110
Metabolic Pathways	Not Available	Not Available
Pentose Phosphate Pathway	SMP00031	map00030
Dna replication	Not Available	map03030

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	50.8 g/L	ALOGPS
logP	0.28	ALOGPS
logP	0.26	ChemAxon
logS	-0.35	ALOGPS
pKa (Strongest Acidic)	17.73	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.64 m³·mol⁻¹	ChemAxon
Polarizability	12.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9000000000-d92e1919424eac03a7b0	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014j-8900000000-0939439a09c8f7b2e93e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9500000000-61e195dbb4527ae29973	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9000000000-62487cfd16429e9987db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-4f7742ff49533756a116	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-3900000000-5dd73a1849e09ffe97f6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0005-9100000000-d506ae3a57d26118dc6f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-9000000000-c8a6489ae02a5c461b88	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-9000000000-fdcbb1c7525a2d2b215f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-004l-9000000000-d90562a5cfb0bfa4edd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-3900000000-0eebb1bf4507776306dd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-9100000000-057abf81800767fcc8ef	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0007-9000000000-bbf5a0c5b8967d589b83	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9000000000-32eba5bb2c4f125d9a03	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum