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Name Description
id 64
T3DB ID T3D0072
Name 2-Oxohexane
Class SmallMolecule
Description 2-Oxohexane is a volatile organic compound. 2-Oxohexane is occasionally found as a volatile component of normal human biofluids. 2-Oxohexane is an hexacarbon solvent; the neurotoxicity of hexacarbon solvents has become apparent and an extensive literature has already developed as a result of the clinical and epidemiological implications of the human disease. The main neurological disorders associated with chronic volatile substance are peripheral neuropathy, cerebellar disease, chronic encephalopathy and dementia. Apart from peripheral neuropathy, the clinical features are non-specific, evidence for solvent-related toxicity is in most cases circumstantial and there is no clear dose/response relationship. (A7698, A7699, A7700).
Categories "Industrial/Workplace Toxin", "Food Toxin", "Natural Toxin"
Types "Organic Compound", "Solvent", "Ketone", "Food Toxin", "Metabolite", "Industrial/Workplace Toxin", "Natural Compound"
Synonyms "2-Hexanone", "2-Hexanone Methyl N-butyl ketone", "Butyl methyl ketone", "Hexan-2-one", "Methyl butyl ketone", "Methyl N-butyl ketone", "MNBK", "N-Butyl methyl ketone", "Propylacetone"
CAS Number 591-78-6
Chemical Formula C6H12O
Average Molecular Mass 100.16
Monoisotopic Mass 100.09
IUPAC Name hexan-2-one
Traditional Name hexanone
SMILES CCCCC(C)=O
InChI Identifier InChI=1S/C6H12O/c1-3-4-5-6(2)7/h3-5H2,1-2H3
InChI Key InChIKey=QQZOPKMRPOGIEB-UHFFFAOYSA-N
Kingdom Organic Compounds
Super Class Organooxygen Compounds
Class Carbonyl Compounds
Sub Class
Direct Parent Ketones
Alternate Parents
Geometric Description Aliphatic Acyclic Compounds
Substituents "Carbonyl Group", "Aliphatic Acyclic Compound"
Descriptors "Oxygenated hydrocarbons (Lipid Maps)"
Status Detected and Not Quantified
Origin Exogenous
Cellular Locations "Cytoplasm", "Extracellular"
Biofluids
Tissues
Pathways
State Liquid
Appearance Colorless liquid.
Melting Point -55.5°C
Boiling Point
Solubility 17.5 mg/mL at 20°C
LogP 1.38
Route of Exposure Oral (L176); inhalation (L176) ;dermal (L176)
Mechanism of Toxicity 2-Hexanone's toxicity is believed to be caused by covalent binding of its metabolites, especially 2,5-hexanedione, with axonal components of nerve tissue and inhibition of enzymes associated with the production of energy in this tissue. 2-Hexanone and 2,5-hexanedione may also inhibit sulfhydryl-dependent enzymes such as fructose-6-phosphate kinase and glyceraldehyde-3-phosphate dehydrogenase, as well as certain creatine kinases and adenylate kinases, impairing energy metabolism and subsequently resulting in axon deterioration. In addition, 2,5-hexanedione can covalently cross-links neurofilaments, causing large axonal swellings. (L176, A124, A125)
Metabolism 2-Hexanone is absorbed via ingestion, inhalation, and dermal routes, then distributed widely throughout the body, with the highest levels in the liver and blood. Metabolism is likely similar to that of other aliphatic ketones, proceeding via reduction to the corresponding secondary alcohol, 2-hexanol. An alternate pathway is oxidation to the corresponding alcohol, 5-hydroxy-2-hexanone, followed by further oxidation to the diketone 2,5-hexanedione. 2-Hexanone and its metabolites are excreted via exhalation or in the urine. (L176)
Toxicity LD50: 2590 mg/kg (Oral, Rat) (T13) LD50: 4800 mg/kg (Dermal, Rabbit) (T13)
Lethal Dose
Carcinogenicity No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources 2-Hexanone was used in the past in paint and paint thinner, to make other chemical substances, and to dissolve oils and waxes. Today it is formed as a waste product resulting from industrial activities such as wood pulping, coal gasification, and oil shale operations. (L176)
Minimum Risk Level
Health Effects Breathing 2-hexanone affects the nervous and reproductive systems. This may include pathologies such as peripheral neuropathy and developmental defects. (L176)
Symptoms Chronic 2-hexanone exposure causes weakness, numbness, tingling in the skin of the hands and feet, irritation to the lungs, and narcosis. (L176)
Treatment
DrugBank ID
HMDB ID HMDB05842
PubChem Compound ID 11583
ChEMBL ID CHEMBL195861
ChemSpider ID 11095
KEGG Compound ID
UniProt ID 0
OMIM ID 0
ChEBI ID 421633
BioCyc ID 2K-ADIPATE
CTD ID D008742
Stitch ID 2-Hexanone
PDB ID
ACToR ID 1960
Wikipedia Link
Creation Date 2009-03-06 18:58:01
Update Date 2014-12-24 20:21:02