Dodecahydroxycyclohexane

Dodecahydroxycyclohexane is an organic compound with molecular formula C6O12H12 or C6(OH)12 or (C(OH)2)6.

It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone (C6O6).

The dihydrate C6O12H12·2H2O can be crystallized from methanol as colorless plates or prisms, that decomposes at about 100 °C.

[1] This compound was synthesized by Joseph Udo Lerch (1816–1892) in 1862[2] by oxidation of benzenehexol C6(OH)6 or tetrahydroxy-p-benzoquinone C6(OH)4O2 and characterized by Rudolf Nietzki and Theodor Benckiser [de] in 1885,[3] although the product was for a long time assumed to be hexaketocyclohexane with water of crystallization (C6O6·8H2O).

Its true nature was suspected since the 1950s or earlier,[4] but was confirmed by X-ray diffraction analysis only in 2005.

Thermal ellipsoid model of the molecular cell of dodecahydroxycyclohexane dihydrate