ACETONYLACETONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C6H10O2
Molecular Weight	114.1424
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CCC(C)=O

InChI

InChIKey=OJVAMHKKJGICOG-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C6H10O2
Molecular Weight	114.1424
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Suppression of radiation-induced testicular germ cell apoptosis by 2,5-hexanedione pretreatment. III. Candidate gene analysis identifies a role for fas in the attenuation of X-ray-induced apoptosis.	2010-10	20616204
Gamma-diketone axonopathy: analyses of cytoskeletal motors and highways in CNS myelinated axons.	2010-09	20554699
Occupational neurologic disorders in Korea.	2010-06	20607045
The effect of 2,5-hexanedione on permeability of blood-nerve barrier in rats.	2010-06	20051453
[Effect of 2,5-hexanedione on myelin protein zero in sciatic nerve and its antibody in serum of rats at different time points].	2010-05	20568451
Engineering cofactor preference of ketone reducing biocatalysts: A mutagenesis study on a γ-diketone reductase from the yeast Saccharomyces cerevisiae serving as an example.	2010-04-14	20480039
Highly efficient and stereoselective biosynthesis of (2S,5S)-hexanediol with a dehydrogenase from Saccharomyces cerevisiae.	2010-04-07	20237665
Remarkable iodine-catalyzed synthesis of novel pyrrole-bearing N-polyaromatic beta-lactams.	2010-02-23	20335963
[The effect of 2,5-hexanedione on nerve growth factor in sciatic nerve of rats and VSC4.1 cell].	2010-01	20388358
Degradation of hexane and other recalcitrant hydrocarbons by a novel isolate, Rhodococcus sp. EH831.	2010-01	19756804
The background of mitochondrial DNA haplogroup J increases the sensitivity of Leber's hereditary optic neuropathy cells to 2,5-hexanedione toxicity.	2009-11-19	19936068
New insights into mechanisms of gamma-diketone-induced axonopathy.	2009-11	19404740
Workplace exposures and the risk of amyotrophic lateral sclerosis.	2009-09	19750102
The effect of workload on biological monitoring of occupational exposure to toluene and n-Hexane: contribution of physiologically based toxicokinetic modeling.	2009-07	19384711
Neurotoxic effect of 2,5-hexanedione on neural progenitor cells and hippocampal neurogenesis.	2009-06-16	19464574
[Effects of garlic oil on n-hexane metabolized to 2, 5-hexanedione in mice serum].	2009-05	19538836
Determination of 2,5-hexanedione in urine by headspace solid-phase microextraction and gas chromatography.	2009-05	19470226
Probing mechanisms of axonopathy. Part II: Protein targets of 2,5-hexanedione, the neurotoxic metabolite of the aliphatic solvent n-hexane.	2009-02	19033394
Comparative covalent protein binding of 2,5-hexanedione and 3-acetyl-2,5-hexanedione in the rat.	2009	19557614
[Effects of garlic oil on 2, 5-HD induced lipid peroxidation damage in rat nerve tissues].	2008-11	19467181
2,5-hexanedione (HD) treatment alters calmodulin, Ca2+/calmodulin-dependent protein kinase II, and protein kinase C in rats' nerve tissues.	2008-10-01	18582483
[Dynamic study of neurofilament contents in rat's spinal cord induced by 2, 5-hexanedione].	2008-10	19272251
Resveratrol reestablishes spermatogenesis after testicular injury in rats caused by 2, 5-hexanedione.	2008-07-05	18710639
Laboratory evolution of Pyrococcus furiosus alcohol dehydrogenase to improve the production of (2S,5S)-hexanediol at moderate temperatures.	2008-07	18452026
Involvement of cyclin-dependent kinase 5 in 2,5-hexanedione-induced neuropathy.	2008-06-03	18423835
Spermatid head retention as a marker of 2,5-hexanedione-induced testicular toxicity in the rat.	2008-06	18467684
Re-establishment of spermatogenesis by diethylstilbestrol after 2,5-hexanedione-induced irreversible testicular atrophy in rats.	2008-04	18480992
Polyneuropathy induced by n-hexane intoxication in Taiwan.	2008-03	18564821
Changes of cytoskeletal proteins in nerve tissues and serum of rats treated with 2,5-hexanedione.	2008-02-28	18177991
The reversibility of neurofilaments decline induced by 2,5-hexanedione in rat nerve tissues.	2008-02-01	18001694
Inhalant abuse detection and evaluation in young Tunisians.	2008-01	18279264
A comparison of the apoptotic and cytotoxic effects of hexanedione derivatives on human non-neuronal lines and the neuroblastoma line SH-SY5Y.	2008-01	17973901
Enzymatic characteristics of an aldo-keto reductase family protein (AKR1C15) and its localization in rat tissues.	2007-09-01	17574202
Expression of Bcl-2, Bax and Caspase-3 in nerve tissues of rats chronically exposed to 2,5-hexanedione.	2007-09	17492505
Dose-dependent effects of sertoli cell toxicants 2,5-hexanedione, carbendazim, and mono-(2-ethylhexyl) phthalate in adult rat testis.	2007-08	17763286
Time-dependent alteration of cytoskeletal proteins in cerebral cortex of rat during 2,5-hexanedione-induced neuropathy.	2007-08	17447142
[Resveratrol helps restore spermatogenesis after testis injury induced by 2,5-hexanedione].	2007-07	17725299
Effect of physical exertion on the biological monitoring of exposure to various solvents following exposure by inhalation in human volunteers: II. n-Hexane.	2007-07	17503295
Diketone radical cations: ketonic and enolic forms as revealed by matrix EPR studies and DFT calculations.	2007-05-03	17428039
[Effect of nerve growth factor on mitochondrion dysfunction of motor neuron induced by 2,5-hexanedione].	2007-05	17712933
Apoptotic and necrotic effects of hexanedione derivatives on the human neuroblastoma line SK-N-SH.	2007-03-07	17229511
Two new reactive targets of 2,5-hexanedione in vitro - beta-alanine and glycine.	2007-02	16733615
Activation of soluble guanylate cyclase by nitric oxide is increased in lymphocytes from both rats chronically exposed to 2,5-hexanedione and workers chronically exposed to n-hexane.	2007-01-05	17125898
Grand rounds: could occupational exposure to n-hexane and other solvents precipitate visual failure in leber hereditary optic neuropathy?	2007-01	17366829
Synthesis of enantiopure (5R)-hydroxyhexane-2-one with immobilised whole cells of Lactobacillus kefiri.	2006-07	16292648
[Effect of 2, 5-hexanedione on calcium homeostasis of motor neuron].	2006-05	16737585
Association between metabolic gene polymorphisms and susceptibility to peripheral nerve damage in workers exposed to n-hexane: a preliminary study.	2006-02-18	16484137
Changes in cytosolic Ca2+ levels regulate Bcl-xS and Bcl-xL expression in spermatogenic cells during apoptotic death.	2006-01-27	16301318
Spectrophotometric analysis of solubilized rat hair proteins following intraperitoneal injection of 2,5-hexanedione.	2002	20021169
Experimental neuropathy produced by 2,5-hexanedione--a major metabolite of the neurotoxic industrial solvent methyl n-butyl ketone.	1975-08	171344

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:49:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:49:01 GMT 2025`
Record UNII	C0Z8884J3P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ACETONYLACETONE

Systematic Name

English

NSC-7621

Preferred Name

English

ACETONYLACETONE [MI]

Common Name

English

2,5-HEXANEDIONE

Systematic Name

English

.ALPHA.,.BETA.-DIACETYLETHANE

Systematic Name

English

2,5-DIOXOHEXANE

Systematic Name

English

HEXANEDIONE, 2,5-

Systematic Name

English

1,2-DIACETYLETHANE

Systematic Name

English

2,5-DIKETOHEXANE

Systematic Name

English

DIACETONYL

Common Name

English

Code System Code Type Description

NSC

7621