Cyclohexanehexone
Encyclopedia
Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is a organic compound
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with formula C6O6, the sixfold ketone
Ketone
In organic chemistry, a ketone is an organic compound with the structure RCR', where R and R' can be a variety of atoms and groups of atoms. It features a carbonyl group bonded to two other carbon atoms. Many ketones are known and many are of great importance in industry and in biology...

 of cyclohexane
Cyclohexane
Cyclohexane is a cycloalkane with the molecular formula C6H12. Cyclohexane is used as a nonpolar solvent for the chemical industry, and also as a raw material for the industrial production of adipic acid and caprolactam, both of which being intermediates used in the production of nylon...

. It is an oxide
Oxide
An oxide is a chemical compound that contains at least one oxygen atom in its chemical formula. Metal oxides typically contain an anion of oxygen in the oxidation state of −2....

 of carbon
Carbon
Carbon is the chemical element with symbol C and atomic number 6. As a member of group 14 on the periodic table, it is nonmetallic and tetravalent—making four electrons available to form covalent chemical bonds...

 (an oxocarbon
Oxocarbon
An oxocarbon or oxide of carbon is an inorganic compound consisting only of carbon and oxygen.The simplest and most common oxocarbons are carbon monoxide and carbon dioxide...

), indeed a hexamer
Polymer
A polymer is a large molecule composed of repeating structural units. These subunits are typically connected by covalent chemical bonds...

 of carbon monoxide
Carbon monoxide
Carbon monoxide , also called carbonous oxide, is a colorless, odorless, and tasteless gas that is slightly lighter than air. It is highly toxic to humans and animals in higher quantities, although it is also produced in normal animal metabolism in low quantities, and is thought to have some normal...

.

As of May 2006, this compound had yet to be synthesized in bulk.

Related compounds

Cyclohexanehexone can be viewed as the neutral counterpart of the rhodizonate
Rhodizonic acid
Rhodizonic acid is a chemical compound with formula C6H2O6 or 42. It can be seen as a two-fold alcohol and four-fold ketone of cyclohexene, more precisely 5,6-dihydroxycyclohex-5-ene-1,2,3,4-tetrone....

 anion . The singly charged anion has been detected in mass spectrometry
Mass spectrometry
Mass spectrometry is an analytical technique that measures the mass-to-charge ratio of charged particles.It is used for determining masses of particles, for determining the elemental composition of a sample or molecule, and for elucidating the chemical structures of molecules, such as peptides and...

 experiments by R. Wyrwas and C. Jarrold, formed by oligomerization of carbon monoxide through the formation molybdenum
Molybdenum
Molybdenum , is a Group 6 chemical element with the symbol Mo and atomic number 42. The name is from Neo-Latin Molybdaenum, from Ancient Greek , meaning lead, itself proposed as a loanword from Anatolian Luvian and Lydian languages, since its ores were confused with lead ores...

 carbonyl
Carbonyl
In organic chemistry, a carbonyl group is a functional group composed of a carbon atom double-bonded to an oxygen atom: C=O. It is common to several classes of organic compounds, as part of many larger functional groups....

s.

According to X-ray diffraction analysis, the reagent
Reagent
A reagent is a "substance or compound that is added to a system in order to bring about a chemical reaction, or added to see if a reaction occurs." Although the terms reactant and reagent are often used interchangeably, a reactant is less specifically a "substance that is consumed in the course of...

 traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually dodecahydroxycyclohexane
Dodecahydroxycyclohexane
Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C612. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone .-Dihydrate:...

 dihydrate, a solid that decomposes at 95°C.

In 1966, H. E. Worne of Natick Chemical Industries patented compounds with formulas C10O8 and C14O10, which can be described as the fusion of two or three molecules of C6O6, claimed to be produced by the action of ultraviolet radiation on a hot water solution of the parent compound.

Triquinoyl therapy

In the late 1940s, W. Hale claimed that triquinoyl, being a trimer
Trimer (chemistry)
In chemistry, a trimer is a product derived from three identical precursors. Trimers are typically cyclic. Chemical compounds that often trimerise are aliphatic isocyanates and cyanic acids. Often, trimerization competes with polymerization....

 of W. Koch
William Frederick Koch
William Frederick Koch was a U. S. medical doctor and pharmaceutical entrepreneur. In the 1940s he marketed glyoxylide, a drug which he claimed would cure cancer. The claims were never scientifically proved, and he was considered a charlatan by the FDA.-Biography:William Koch got a BA in...

's glyoxylide, should be just as effective as the latter against "diabetes, arthritis, poliomyelitis, and even cancer". Even though there is no research supporting this claim (and Koch's glyoxylide preparations were found to be just distilled water), triquinoyl is still listed as an ingredient of some alternative medicine
Alternative medicine
Alternative medicine is any healing practice, "that does not fall within the realm of conventional medicine." It is based on historical or cultural traditions, rather than on scientific evidence....

 remedies.

See also

  • Cyclopentanepentone
    Cyclopentanepentone
    Cyclopentanepentone, also known as leuconic acid, is a hypothetical organic compound with formula C5O5, the fivefold ketone of cyclopentane...

  • Ethylenetetracarboxylic dianhydride
    Ethylenetetracarboxylic dianhydride
    Ethylenetetracarboxylic dianhydride is a chemical compound with formula , that can be seen as the twofold anhydride of ethylenetetracarboxylic acid . Its molecular backbone consists of two five-atom maleic anhydride rings, each containing one oxygen atom and four carbon atoms, sharing a pair of...

    , an isomer of .
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