Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The s ...
with formula , the sixfold
ketone
In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...
of
cyclohexane. It is an
oxide
An oxide () is a chemical compound that contains at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion of oxygen, an O2– (molecular) ion. with oxygen in the oxidation state of −2. Most of the ...
of
carbon (an
oxocarbon
In chemistry, an oxocarbon or oxide of carbon is a chemical compound consisting only of carbon and oxygen. The simplest and most common oxocarbons are carbon monoxide (CO) and carbon dioxide (). Many other stable (practically if not thermodynam ...
), a
hexamer
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
of
carbon monoxide
Carbon monoxide (chemical formula CO) is a colorless, poisonous, odorless, tasteless, flammable gas that is slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the simpl ...
.
The compound is expected to be highly unstable, unlike the
cyclohexanehexathione analog, and as of 1999 had only been observed as an ionized fragment during
mass spectrometry
Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...
studies.
Related compounds
Cyclohexanehexone can be viewed as the neutral counterpart of the
rhodizonate anion
An ion () is an atom or molecule with a net electrical charge.
The charge of an electron is considered to be negative by convention and this charge is equal and opposite to the charge of a proton, which is considered to be positive by conven ...
. The singly charged anion has been detected in
mass spectrometry
Mass spectrometry (MS) is an analytical technique that is used to measure the mass-to-charge ratio of ions. The results are presented as a ''mass spectrum'', a plot of intensity as a function of the mass-to-charge ratio. Mass spectrometry is used ...
experiments, formed by
oligomerization
In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
of carbon monoxide through the formation of
molybdenum
Molybdenum is a chemical element with the symbol Mo and atomic number 42 which is located in period 5 and group 6. The name is from Neo-Latin ''molybdaenum'', which is based on Ancient Greek ', meaning lead, since its ores were confused with l ...
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. A compound containing a ...
s.
According to
X-ray diffraction
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angle ...
analysis, the
reagent
In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...
traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually
dodecahydroxycyclohexane
Dodecahydroxycyclohexane is an organic compound with molecular formula or or . It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone ().
Dihydrate
The dihydrate can be crystalli ...
dihydrate—the
geminal diol
In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached ...
derivative of the six ketone groups with an additional two molecules of water—a solid that decomposes at 95 °C.
In 1966, Howard E. Worne of Natick Chemical Industries patented compounds with formulas and , which can be described as the fusion of two or three molecules of , claimed to be produced by the action of
ultraviolet radiation
Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30 PHz) to 400 nm (750 THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
on a hot water solution of the parent compound.
Triquinoyl therapy
In the late 1940s, William J. Hale claimed that "triquinoyl", being a
trimer of
William Frederick Koch'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 is any practice that aims to achieve the healing effects of medicine despite lacking biological plausibility, testability, repeatability, or evidence from clinical trials. Complementary medicine (CM), complementary and alt ...
remedies.
See also
*
Cyclopentanepentone
Cyclopentanepentone, also known as leuconic acid, is a hypothetical organic compound with formula C5O5, the fivefold ketone of cyclopentane. It would be an oxide of carbon (an oxocarbon), indeed a pentamer of carbon monoxide.
As of 2000, the comp ...
*
Ethylenetetracarboxylic dianhydride
Ethylenetetracarboxylic dianhydride is a chemical compound with formula , that can be seen as the twofold anhydride of ethylenetetracarboxylic acid . It has a bicyclic molecular structure consisting of two maleic anhydride rings fused by thei ...
, an isomer of .
*
Cyclohexanehexathione, with same structure but with sulfur instead of oxygen.
References
{{Oxides of carbon
Oxocarbons
Hypothetical chemical compounds
Cyclic ketones
Polyketones
Conjugated ketones