Dodecahydroxycyclohexane

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Dodecahydroxycyclohexane
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Appearance Colourless crystals (dihydrate)

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Dodecahydroxycyclohexane is an organic compound with molecular formula Template:Chem2 or Template:Chem2 or Template:Chem2. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone (Template:Chem2).

Dihydrate

The dihydrate Template:Chem2 can be crystallized from methanol as colorless plates or prisms, that decomposes at about 100 °C.[1]

File:Dodecahydroxycyclohexane-dihydrate-from-xtal-CM-3D-ellipsoids.png
Thermal ellipsoid model of the molecular cell of dodecahydroxycyclohexane dihydrate

This compound was synthesized by Joseph Udo Lerch (1816–1892) in 1862[2] by oxidation of benzenehexol Template:Chem2 or tetrahydroxy-p-benzoquinone Template:Chem2 and characterized by Rudolf Nietzki and Template:Ill in 1885,[3] although the product was for a long time assumed to be hexaketocyclohexane with water of crystallization (Template:Chem2).

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

References

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