Cyclohexanehexone
| |
| Names | |
|---|---|
| IUPAC name
cyclohexane-1,2,3,4,5,6-hexone
| |
| Other names
hexaketocyclohexane, triquinoyl
| |
| Identifiers | |
| ECHA InfoCard | 100.007.649 |
CompTox Dashboard (EPA)
|
|
| Properties | |
| C6O6 | |
| Molar mass | 168.06 g mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclohexanehexone, also known as cyclohexanehexaone, hexaketocyclohexane, and triquinoyl, is a organic compound with formula C6O6, the sixfold ketone of cyclohexane. It is an oxide of carbon (an oxocarbon), indeed a hexamer of carbon monoxide.
As of May 2006, this compound had yet to be synthesized in bulk[1] [2].
Related compounds
Cyclohexanehexone can be viewed as the neutral counterpart of the rhodizonate anion C
6O2−
6. The singly-charged anion C
6O−
6 has been detected in mass spectroscopy experiments by R. Wyrwas and C. Jarrold, formed by oligomerization of carbon monoxide through the formation molybdenum carbonyls.[3]
According to X-ray diffraction analysis, the reagent traded under the name "cyclohexanehexone octahydrate" or equivalent names is actually dodecahydroxycyclohexane dihydrate;[4][5]
In 1966, H. E. Worne of Natick Chemical Industries patented compounds with formulas C10O10 and C14O14 which can be described as the fusion of two or three molecules of C6O6.[6]
Triquinoyl therapy
In the late 1940s, W. Hale claimed that triquinoyl, being a trimer of W. Koch's glyoxylide, should be just as effective as the latter against "diabetes, arthritis, poliomyelitis, and even cancer".[7] Even though there is no research supporting this claim (and Koch's glyoxylide preparations were found to be just distilled water),[8] triquinoyl is still listed as an ingredient of some alternative medicine remedies.[9][10]
References
- ^
Gunther Seitz (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help) - ^
Detlef Schröder, (1999). "Mass spectrometric studies of the oxocarbons CnOn (n = 3–6)". International Journal of Mass Spectrometry. 188 (1–2): 17–25. doi:10.1016/S1387-3806(98)14208-2.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help); Unknown parameter|month=ignored (help)CS1 maint: extra punctuation (link) - ^ Richard B. Wyrwas and Caroline Chick Jarrold (2006), Production of C6O6- from Oligomerization of CO on Molybdenum Anions. J. Am. Chem. Soc. volume 128 issue 42, pages 13688–13689. doi:10.1021/ja0643927
- ^
Thomas M. Klapötke (2005). "Dodecahydroxycyclohexane dihydrate" (PDF). Acta Crystallographica, Section E - Structure Reports Online.
{{cite journal}}: Unknown parameter|coauthors=ignored (|author=suggested) (help); Unknown parameter|month=ignored (help) - ^ Willis B. Person and Dale G. Williams (1957), "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem., 61 (7), 1017-1018. DOI: 10.1021/j150553a047
- ^ Howard E Worne, United States Patent 3,227,641, "POLYCARBONYLS", issued Jan 4, 1966
- ^ William J. Hale (1949), "Farmer Victorious"
- ^ William W. Goodrich (1986), interview for FDA History (Part 2)
- ^ U. S. Food and Drug Administration (1989), Import Alert #66-46 - Unapproved Version of Rodaquin
- ^ Renewal & Wellness, LLC (2009) Protocel, an alternative medicine claimed to contain triquinoyl. Last accessed on March 25, 2009
See also
- Cyclopentanepentone
- Ethylenetetracarboxylic dianhydride, an isomer of C
6O
6.