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. Th ...

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 bon ...

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colorless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohex ...

. 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 makes ...

(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 relat ...

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 si ...

. The compound is expected to be highly unstable, unlike the

cyclohexanehexathione Cyclohexanehexathione is a cyclic covalent compound consisting of a six-carbon ring with a sulfur bonded to each. It has been generated by neutralization of its monoanion () in a mass spectrometer. This compound is the thioketone analog of cycl ...

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 u ...

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

experiments, formed by oligomerization 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 le ...

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 containin ...

s. According to X-ray diffraction analysis, the reagent traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually dodecahydroxycyclohexane dihydrate—the geminal diol 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 nanometer, nm (with a corresponding frequency around 30 Hertz, PHz) to 400 nm (750 Hertz, THz), shorter than that of visible light, but longer than ...

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 William Frederick Koch (1885–1967) 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 c ...

glyoxylide Ethylene dione or ethylenedione, also called dicarbon dioxide, Carbon peroxide, ethenedione, or ethene-1,2-dione, is a chemical compound with the formula or . It is an oxide of carbon (an oxocarbon), and can be described as the carbon-carbon ...

, 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 ...

remedies.

References

{{Oxides of carbon Oxocarbons Hypothetical chemical compounds Cyclic ketones Polyketones Conjugated ketones

Related compounds

Triquinoyl therapy

See also

References