Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2019/06/06 04:42:26」(JST)

wiki en

2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. 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.^[1]

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.

Mechanism of action

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.^[2] 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.^[3]

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.^[4]

Synthesis

A Process for preparing 2,5-hexanedione has been described:^[5]^[6]

Uses

Acetonylacetone can be used in the synthesis of isocarboxazid,^[7] rolgamidine,^[8] and mopidralazine.

References

^ Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annu. Rev. Pharmacol. Toxicol. 1982;22:145-66.
^ Stephen R Clough; Leyna Mulholland (2005), "Hexane", Encyclopedia of Toxicology, 2 (2nd ed.), Elsevier, pp. 522–525
^ Hardo Siegel; Manfred Eggersdorfer (2007), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 16
^ Wolfgang Dekant; Spiridon Vamvakas (2007), "Toxicology", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 23
^ U.S. Patent 3,819,714
^ http://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.
^ U.S. Patent 2,908,688
^ U.S. Patent 4,140,793

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 小児における後天性末梢性ニューロパチーの概要overview of acquired peripheral neuropathies in children [show details]
…hands and feet. Sensory symptoms are minimal and consist of numbness . Other solvents such as 2, 5-hexanedione and methyl-n-butylketone cause a similar neuropathy. After elimination of the exposure, recovery…

English Journal

Ultrasound-Promoted One-Pot Synthesis of Mono- or Bis-Substituted Organylselanyl Pyrroles.

Peglow TJ, Costa GPD, Duarte LFB, Silva MS, Barcellos T, Perin G, Alves D.
The Journal of organic chemistry. 2019 May;84(9)5471-5482.
A simple method for the direct mono- and bis-organylselenylation of N-substituted pyrroles through a multicomponent reaction promoted by ultrasonic radiation was described. These sonochemical promoted reactions were performed between different primary amines, 2,5-hexanedione and dialkyl, diheteroary
PMID 31020836

Carbonyl reductase sniffer from the model organism daphnia: Cloning, substrate determination and inhibitory sensitivity.

Strehse JS, Protopapas N, Maser E.
Chemico-biological interactions. 2019 Apr;307()29-36.
Carbonyl reductases (CRs) represent a fundamental enzymatic defense mechanism against oxidative stress. While commonly two carbonyl reductases (CBR1 and CBR3) are found in mammalian genomes, invertebrate model organisms like Drosophila melanogaster express no CR but a functional homolog to human CBR
PMID 30991043

Pyrrole adducts in globin and plasma of workers exposed to hexane.

Ichihara G, Amarnath V, Valentine HL, Takeshita T, Morimoto K, Sobue T, Kawai T, Valentine WM.
International archives of occupational and environmental health. 2019 Apr;().
Urinary excretion of 2,5-hexanedione is currently used to estimate the exposure levels of hexane occurring to an individual during the previous work shift. However, because hexane exposures and urinary 2,5-hexanedione levels can vary considerably from day to day, and subchronic to chronic exposures
PMID 30955093

Japanese Journal

種々の固体触媒を用いた2,5-ヘキサンジオンの環化反応活性と触媒性質の関連

西村俊,大松新太郎,海老谷幸喜
石油学会年会・秋季大会講演要旨集 2018f(0), 53, 2018
… バイオマス由来化合物である5-ヒドロキシメチルフルフラール（HMF）を経て得られる2,5-ヘキサンジオンの分子内アルドール反応により、選択的に3-メチル-2-シクロペンテノンを合成するプロセスに着目した。 …
NAID 130007534032

Taurine inhibits 2,5-hexanedione-induced oxidative stress and mitochondria-dependent apoptosis in PC12 cells

LI Shuangyue,GUAN Huai,QIAN Zhiqiang,SUN Yijie,GAO Chenxue,LI Guixin,YANG Yi,PIAO Fengyuan,HU Shuhai
Ｉｎｄｕｓｔｒｉａｌ　ｈｅａｌｔｈ 55(2), 108-118, 2017
… <p>2,5-hexanedione (HD) is the ultimate neurotoxic metabolite of hexane, causing the progression of nerve diseases in human. … HD also induced the disturbance of Bax and Bcl-2 expression, the loss of MMP, the release of mitochondrial cytochrome c and caspase-3 activation in PC12 cells. …
NAID 130005558267

2,5-hexanedione induced apoptosis of rat bone marrow mesenchymal stem cells by reactive oxygen species

Liu Shuang,Chen Feng,Wang Longjuan,Sun Wenchang,Liu Qigui,Chen Haibo,Su Dan,Jiang Yue,Piao Fengyuan,Sun Xiance,Sun Wenfang
Journal of Occupational Health 58(2), 170-178, 2016-03
NAID 40020804283

Related Pictures

hexadione 1 2 diacetylethane 2 5 AddexBio Product Detail - 2,5-Hexanedione File:Synthesis 2,5-Hexanedione C.svg Chemical structure of 2,5-hexanedione DIMETHYL-2,5-HEXANEDIONE Chemical 800105 2,5-Hexanedione acetone diacetonyl 2 5 dioxohexane 2 Hexanedione_Molecular_structure_CAS

★リンクテーブル★

リンク元	「2,5-ヘキサンジオン」

「2,5-ヘキサンジオン」

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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:85104 ;
ChemSpider	7744 ;
ECHA InfoCard	100.003.400
PubChem CID	8035;
RTECS number	MO3150000
CompTox Dashboard (EPA)	DTXSID8030138 ;
	InChI InChI=1S/C6H10O2/c1-5(7)3-4-6(2)8/h3-4H2,1-2H3 Key: OJVAMHKKJGICOG-UHFFFAOYSA-N ; 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).
	verify (what is ?)
	Infobox references

　　[★]

英: 2,5-hexanedione, 2,5-HD
関: ヘキサン、尿中2,5-ヘキサンジオン、ノルマルヘキサン中毒

[1] Couri D, Milks M. "Toxicity and metabolism of the neurotoxic hexacarbons n-hexane, 2-hexanone, and 2,5-hexanedione" Annu. Rev. Pharmacol. Toxicol. 1982;22:145-66.

[tox-2] Stephen R Clough; Leyna Mulholland (2005), "Hexane", Encyclopedia of Toxicology, 2 (2nd ed.), Elsevier, pp. 522–525

[ket-3] Hardo Siegel; Manfred Eggersdorfer (2007), "Ketones", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 16

[ulltox-4] Wolfgang Dekant; Spiridon Vamvakas (2007), "Toxicology", Ullmann's Encyclopedia of Industrial Chemistry (7th ed.), Wiley, p. 23

[5] U.S. Patent 3,819,714

[6] ttp://www.prepchem.com/synthesis-of-2-5-hexanedione/ Primary: Systematic organic chemistry, by W. M. Cumming, 194, 1937.

[7] U.S. Patent 2,908,688

[8] U.S. Patent 4,140,793

匿名

検索

案内

案内

2,5-hexanedione