Hexane-2,5-dione

Hexane-2,5-dione

Names
Preferred IUPAC name Hexane-2,5-dione
Other names 1,2-Diacetylethane 'α','β'-Diacetylethane Acetonyl acetone Diacetonyl 2,5-Dioxohexane 2,5-Diketohexane 2,5-Hexanedione
Identifiers
CAS Number	110-13-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:85104 N
ChemSpider	7744 Y
ECHA InfoCard	100.003.400
PubChem CID	8035
RTECS number	MO3150000
InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Y Key: OJVAMHKKJGICOG-UHFFFAOYSA-N Y InChI=1/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Key: OJVAMHKKJGICOG-UHFFFAOYAH
SMILES O=C(C)CCC(=O)C
Properties
Chemical formula	C6H10O2
Molar mass	114.1438 g mol−1
Appearance	colorless liquid
Density	0.973 g cm−3, liquid
Melting point	−5.5 °C (22.1 °F; 267.6 K)
Boiling point	191.4 °C (376.5 °F; 464.5 K)
Solubility in water	≥ 10 g/100 mL (22 °C)
Magnetic susceptibility (χ)	-62.51·10−6 cm3/mol
Structure
Molecular shape	trigonal planar at carbonyl tetrahedral elsewhere
Hazards
Flash point	78 °C (172 °F; 351 K)
Related compounds
Related diketones	acetylacetone
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. In humans, it is a toxic metabolite of hexane and of 2-hexanone.

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.

Similar symptoms are observed in animal models. They are associated with a degeneration of the peripheral nervous system (and eventually the central nervous system), starting with the distal portions of the longer and wider nerve axons.

It appears that the neurotoxicity of 2,5-hexanedione resides in its γ-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 γ-diketones are neurotoxic. In fact, higher α-diketones, like 2,3-pentanedione and 2,3-hexanedione, are found in small amounts in various foods. They are used as aroma components in alcohol-free beverages and in baked goods.

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.

A Process for preparing 2,5-hexanedione has been described:

Acetonylacetone can be used in the synthesis of isocarboxazid,rolgamidine, and mopidralazine.