Names | |
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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 | |
3D model (JSmol) | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.003.400 |
EC Number |
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PubChem CID | |
RTECS number |
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UNII | |
UN number | 1224 |
CompTox Dashboard (EPA) | |
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Properties | |
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) |
≥ 10 g/100 mL (22 °C) | |
-62.51·10−6 cm3/mol | |
Structure | |
trigonal planar at carbonyl tetrahedral elsewhere | |
Hazards | |
GHS labelling: | |
Warning | |
H315, H319, H373 | |
P260, P264, P280, P302+P352, P305+P351+P338, P314, P321, P332+P313, P337+P313, P362, P501 | |
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). |
2,5-Hexanedione (Acetonylacetone) is an aliphatic diketone. It is a colorless liquid. [1] 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. [2]
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, whereas 2,5-heptanedione and 3,6-octanedione and other γ-diketones are. [3]
2,5-Hexanedione reacts with lysine residues in axonal proteins by Schiff base formation followed by cyclization to give pyrroles. Oxidation of the pyrrole residues then causes cross-linking and denaturation of proteins, which perturbs axonal transport and function and causes damage to nerve cells. [4]
2,5-Hexanedione has been prepared in several ways. [5] A common method involves hydrolysis of 2,5-dimethylfuran, a glucose derived heterocycle. [1]
Acetonylacetone can be used in the synthesis of isocarboxazid, [6] rolgamidine, [7] and mopidralazine. Treatment with P4S10 gives 2,5-dimethylthiophene.
A toxin is a naturally occurring organic poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919) and is derived from the word "toxic".
Hexane or n-hexane is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14.
Muscarine, L-(+)-muscarine, or muscarin is a natural product found in certain mushrooms, particularly in Inocybe and Clitocybe species, such as the deadly C. dealbata. Mushrooms in the genera Entoloma and Mycena have also been found to contain levels of muscarine which can be dangerous if ingested. Muscarine has been found in harmless trace amounts in Boletus, Hygrocybe, Lactarius and Russula. Trace concentrations of muscarine are also found in Amanita muscaria, though the pharmacologically more relevant compound from this mushroom is the Z-drug-like alkaloid muscimol. A. muscaria fruitbodies contain a variable dose of muscarine, usually around 0.0003% fresh weight. This is very low and toxicity symptoms occur very rarely. Inocybe and Clitocybe contain muscarine concentrations up to 1.6%.
Neurotoxins are toxins that are destructive to nerve tissue. Neurotoxins are an extensive class of exogenous chemical neurological insults that can adversely affect function in both developing and mature nervous tissue. The term can also be used to classify endogenous compounds, which, when abnormally contacted, can prove neurologically toxic. Though neurotoxins are often neurologically destructive, their ability to specifically target neural components is important in the study of nervous systems. Common examples of neurotoxins include lead, ethanol, glutamate, nitric oxide, botulinum toxin, tetanus toxin, and tetrodotoxin. Some substances such as nitric oxide and glutamate are in fact essential for proper function of the body and only exert neurotoxic effects at excessive concentrations.
In organic chemistry, a dicarbonyl is a molecule containing two carbonyl groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls are in close enough proximity that their reactivity is changed, such as 1,2-, 1,3-, and 1,4-dicarbonyls. Their properties often differ from those of monocarbonyls, and so they are usually considered functional groups of their own. These compounds can have symmetrical or unsymmetrical substituents on each carbonyl, and may also be functionally symmetrical or unsymmetrical.
Furan is a heterocyclic organic compound, consisting of a five-membered aromatic ring with four carbon atoms and one oxygen atom. Chemical compounds containing such rings are also referred to as furans.
Dicofol is an insecticide, an organochlorine that is chemically related to DDT. Dicofol is a miticide that is very effective against spider mite. Its production and use is banned internationally under the Stockholm Convention.
Petroleum ether is the petroleum fraction consisting of aliphatic hydrocarbons and boiling in the range 35–60 °C, and commonly used as a laboratory solvent. Despite the name, petroleum ether is not classified as an ether; the term is used only figuratively, signifying extreme lightness and volatility.
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group α to a carbonyl group (2).
In organic chemistry, the Paal–Knorr Synthesis is a reaction used to synthesize substituted furans, pyrroles, or thiophenes from 1,4-diketones. It is a synthetically valuable method for obtaining substituted furans and pyrroles, which are common structural components of many natural products. It was initially reported independently by German chemists Carl Paal and Ludwig Knorr in 1884 as a method for the preparation of furans, and has been adapted for pyrroles and thiophenes. Although the Paal–Knorr synthesis has seen widespread use, the mechanism wasn't fully understood until it was elucidated by V. Amarnath et al. in the 1990s.
Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant. Other uses include as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics and as an antiwear additive in lubricants. Pure tricresyl phosphate is a colourless, viscous liquid, although commercial samples are typically yellow. It is virtually insoluble in water, but easily soluble in organic solvents like toluene, hexane, and diethylether among others. It was synthesized by Alexander Williamson in 1854 upon reacting phosphorus pentachloride with cresol, though today's manufacturers can prepare TCP by mixing cresol with phosphorus oxychloride or phosphoric acid as well. TCP, especially the all-ortho isomer, is the causative agent in a number of acute poisonings. Its chronic toxicity is also of concern. The ortho-isomer is rarely used on its own outside of laboratory studies that require isomeric purity, due to its extremely toxic nature, and is generally excluded from commercial products where TCP is involved.
Methylecgonidine is a chemical intermediate derived from ecgonine or cocaine.
Cyhalothrin is the ISO common name for an organic compound that, in specific isomeric forms, is used as a pesticide. It is a pyrethroid, a class of synthetic insecticides that mimic the structure and properties of the naturally occurring insecticide pyrethrin which is present in the flowers of Chrysanthemum cinerariifolium. Pyrethroids such as cyhalothrin are often preferred as an active ingredient in agricultural insecticides because they are more cost-effective and longer acting than natural pyrethrins. λ-and γ-cyhalothrin are now used to control insects and spider mites in crops including cotton, cereals, potatoes and vegetables.
2-Hexanone is a ketone used as a general solvent and in paints. It dissolves cellulose nitrate, vinyl polymers and copolymers, and natural and synthetic resins. It is recommended as a solvent because it is photochemically inactive; however it has a very low safe threshold limit value. 2-Hexanone is absorbed through the lungs, orally and dermally and its metabolite, 2,5-hexanedione, is neurotoxic. Animal tests have shown that the neurotoxic effect of 2-hexanone may be potentiated by simultaneous administration of 2-butanone.
2-Fluoroethanol is the organic compound with the formula CH2FCH2OH. This colorless liquid is one of the simplest stable fluorinated alcohols. It was once used as a pesticide. The related difluoro- and trifluoroethanols are far less dangerous.
Tetraethyl pyrophosphate, abbreviated TEPP, is an organophosphate compound with the formula [(C2H5O)2P(O)]2O. It is the tetraethyl derivative of pyrophosphate (P2O74-). It is a colorless oil that solidifies near room temperature. It is used as an insecticide. The compound hydrolyzes rapidly.
Leptophos (O-(4-bromo-2,5-dichlorophenyl) O-methyl phenylphosphonothioate) belongs to the organophosphates and at room temperature it is a stable white solid. It is also known as Phosvel, Abar and Vcs 506. Leptophos was primarily used as a pesticide and fungicide. for rice, cotton, fruit and vegetables until its use was discontinued in 1975 in USA, but still sold in South-Eastern Asia in 1981.
Petroleum benzine is a hydrocarbon-based solvent mixture that is classified by its physical properties rather than a specific chemical composition. This complicates distinction within the long list of petroleum distillate solvent mixtures: mineral spirits, naphtha, petroleum naptha, white gas, white spirits, turps substitute, mineral turpentine, petroleum ether, ligroin, and Stoddard solvent.
5-Nonanone, or dibutyl ketone, is the organic compound with the formula (CH3CH2CH2CH2)2CO. This colorless liquid is a symmetrical ketone.
14-Hydroxygelsenicine (HGE) is a gelsedine-type indole alkaloid naturally found in some plants of the Gelsemium genus. G. elegans was used in traditional Chinese medicine as a remedy for a plethora of conditions such as skin ulcers and dermatitis, pain related to cancer, rheumatic arthritis, psoriasis as well as to treat bone fractures. It can also be found under the names “Duan Chang Cao”, “Gou Wen” and “heartbreak grass”. G. elegans is also known for its toxic effects; it is used by hilltribes of southeastern Asia as an effective means of committing suicide and has been linked to certain types of toxic honey, where HGE was the most abundant component. Gelsedine-type alkaloids from G. elegans usually express high toxicity, with gelsenicine being one of the most toxic. However, toxicity of HGE has not yet been thoroughly researched. More recent studies have shown that alkaloids derived from G. elegans have anti-tumor, anti-inflammatory, analgesic, and immunomodulation properties, with the toxic dose being close to the therapeutic dose.