Cyclohexanehexone

Cyclohexanehexone
IUPAC name cyclohexane-1,2,3,4,5,6-hexone
Other names hexaketocyclohexane, triquinoyl
Identifiers
CAS number	527-31-1
PubChem	68240
ChemSpider	61541 Y
Jmol-3D images	Image 1
SMILES O=C1C(=O)C(=O)C(=O)C(=O)C1=O
InChI InChI=1S/C6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Y Key: PKRGYJHUXHCUCN-UHFFFAOYSA-N Y InChI=1/C6O6/c7-1-2(8)4(10)6(12)5(11)3(1)9 Key: PKRGYJHUXHCUCN-UHFFFAOYAM
Properties
Molecular formula	C6O6
Molar mass	168.06 g mol−1
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cyclohexanehexone, also known as 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 C₆O2−
6. The singly charged anion C₆O−
6 has been detected in mass spectrometry 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, a solid that decomposes at 95°C.^[4][5]

In 1966, H. E. Worne of Natick Chemical Industries patented compounds with formulas C₁₀O₈ and C₁₄O₁₀, which can be described as the fusion of two or three molecules of C₆O₆, claimed to be produced by the action of ultraviolet radiation on a hot water solution of the parent compound.^[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

1. ^ Gunther Seitz; Peter Imming (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews 92 (6): 1227–1260. doi:10.1021/cr00014a004. 
2. ^ Detlef Schröder,; Helmut Schwarz, Suresh Dua, Stephen J. Blanksby and John H. Bowie (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. 
3. ^ Richard B. Wyrwas and Caroline Chick Jarrold (2006), "Production of C6O6⁻ from Oligomerization of CO on Molybdenum Anions". Journal of the American Chemical Society, volume 128, issue 42, pages 13688–13689 PubMed doi:10.1021/ja0643927
4. ^ Thomas M. Klapötke; Kurt Polborn and Jan J. Weigand (2005). "Dodecahydroxycyclohexane dihydrate". Acta Crystallographica E 61: o1393. doi:10.1107/S1600536805010007. 
5. ^ Willis B. Person and Dale G. Williams (1957), "Infrared Spectra and the Structure of Leuconic Acid and Triquinoyl". Journal of Physical Chemistry, volume 61, pages 1017-1018 doi:10.1021/j150553a047
6. ^ Howard E Worne, U.S. Patent 3,227,641 "Polycarbonyls", issued Jan 4, 1966
7. ^ William J. Hale (1949), "Farmer Victorious"
8. ^ William W. Goodrich (1986), interview for FDA History (Part 2)
9. ^ U. S. Food and Drug Administration (1989), Import Alert #66-46 – Unapproved Version of Rodaquin
10. ^ 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 C₆O₆.