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. T ...
with formula , the sixfold
ketone of
cyclohexane. It is an
oxide of
carbon
Carbon () is a chemical element with the symbol C and atomic number 6. It is nonmetallic and tetravalent—its atom making four electrons available to form covalent chemical bonds. It belongs to group 14 of the periodic table. Carbon mak ...
(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 thermodynamica ...
), 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 relative ...
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 simple ...
.
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 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 conve ...
. The singly charged anion has been detected in
mass spectrometry 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 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 containi ...
s.
According to
X-ray diffraction analysis, the
reagent traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually
dodecahydroxycyclohexane
Dodecahydroxycyclohexane is an organic chemistry, 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 ...
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 t ...
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 remedies.
See also
*
Cyclopentanepentone
*
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 their ...
, 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