Dodecahydroxycyclohexane Explained

Dodecahydroxycyclohexane is an 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 can be crystallized from methanol as colorless plates or prisms, that decomposes at about 100 °C.^[1] This compound was synthesized by J. Lerch^[2] in 1862 by oxidation of benzenehexol or tetrahydroxy-p-benzoquinone and characterized by R. Nietzki and others in 1885,^[3] although the product was for a long time assumed to be hexaketocyclohexane with water of crystallization .

Indeed, this product is still commonly marketed as cyclohexanehexone octahydrate, hexaketocyclohexane octahydrate, triquinoyl octahydrate and similar names. Its true nature was suspected since the 1950s or earlier,^[4] but was confirmed by X-ray diffraction analysis only in 2005.^[5]

See also

• Decahydroxycyclopentane

Notes and References

1. Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol). Alexander J. Fatiadi. Horace S. Isbell. William F. Sager. Journal of Research of the National Bureau of Standards Section A. 67A. 2. March–April 1963. 153–162. 10.6028/jres.067A.015. 2009-03-22. https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf. 2009-03-25. dead. 31580622. 6640573.
2. Ueber Kohlenoxydkalium und die aus demselben darstellbaren Säuren. Jos. Ud. Lerch. Journal für Praktische Chemie. 87. 1. 10.1002/prac.18620870146. 1862. 427–469.
3. Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure. R. Nietzki, Th. Benckiser. Berichte der Deutschen Chemischen Gesellschaft. 18. 1. 10.1002/cber.188501801110. 1885. 499–515.
4. 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. 10.1021/j150553a047.
5. Dodecahydroxycyclohexane dihydrate. Thomas M. Klapötke. Kurt Polborn. Jan J. Weigand. Acta Crystallographica E. https://web.archive.org/web/20200304115045/http://journals.iucr.org/e/issues/2005/05/00/ob6498/ob6498.pdf. dead. 2020-03-04. March 2005.