Cyclohexanehexone, also known as hexaketocyclohexane and triquinoyl, is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with formula , the sixfold
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
of
cyclohexane
Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...
. It is an
oxide
An oxide () is a chemical compound containing at least one oxygen atom and one other element in its chemical formula. "Oxide" itself is the dianion (anion bearing a net charge of −2) of oxygen, an O2− ion with oxygen in the oxidation st ...
of
carbon
Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...
(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, monomer, monomers.Quote: ''Oligomer molecule: A molecule of intermediate ...
of
carbon monoxide
Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...
.
The compound is expected to be highly unstable, even less stable than 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 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; it has Symbol (chemistry), symbol Mo (from Neo-Latin ''molybdaenum'') and atomic number 42. The name derived from Ancient Greek ', meaning lead, since its ores were confused with lead ores. Molybdenum minerals hav ...
carbonyl
In organic chemistry, a carbonyl group is a functional group with the formula , composed of a carbon atom double bond, double-bonded to an oxygen atom, and it is divalent at the C atom. It is common to several classes of organic compounds (such a ...
s.
According to
X-ray diffraction
X-ray diffraction is a generic term for phenomena associated with changes in the direction of X-ray beams due to interactions with the electrons around atoms. It occurs due to elastic scattering, when there is no change in the energy of the waves. ...
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 dihydrate—the
geminal diol
A geminal diol (or gem-diol for short) is any organic compound having two hydroxyl functional groups () bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal ...
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 radiation, also known as simply UV, is electromagnetic radiation of wavelengths of 10–400 nanometers, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight and constitutes about 10% of t ...
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 refers to practices that aim to achieve the healing effects of conventional medicine, but that typically lack biological plausibility, testability, repeatability, or supporting evidence of effectiveness. Such practices are ...
remedies.
See also
*
Cyclopentanepentone
*
Ethylenetetracarboxylic dianhydride, 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