Cyclohexanetetrol


A cyclohexanetetrol is a chemical compound consisting of a cyclohexane molecule with four hydroxyl groups replacing four of the twelve hydrogen atoms. It is therefore a cyclitol. Its generic formula is or.
Some cyclohexanetetrols have biologically important roles in some organisms.

Isomers

There are several cyclohexanetetrol isomers that differ on the position of the hydroxyl groups along the ring, and on their orientation relative to the mean plane of the ring.
The isomers with each hydroxyl on a distinct carbon are:
Possible isomers with two geminal hydroxyls are
  • 1,1,2,3-Cyclohexanetetrol ; hydrate of 2,3-dihydroxy-cyclohexanone
  • 1,1,2,4-Cyclohexanetetrol ; hydrate of 2,4-dihydroxy-cyclohexanone
  • 1,1,3,4-Cyclohexanetetrol ; hydrate of 3,4-dihydroxy-cyclohexanone
Possible isomers with two pairs of geminal hydroxyls:
  • 1,1,2,2-Cyclohexanetetrol ; twofold hydrate of 1,2-cyclohexanedione
  • 1,1,3,3-Cyclohexanetetrol ; twofold hydrate of 1,3-cyclohexanedione
  • 1,1,4,4-Cyclohexanetetrol ; twofold hydrate of 1,4-cyclohexanedione

    Preparation

The synthesis of cyclohexanetetrols can be achieved by, among other methods: reduction or hydrogenation of cyclohexenetetrols, tri-hydroxycyclohexanones, pentahydroxycyclohexanones, hydroxylated aromatic hydrocarbons, or hydroxylated quinones; the hydrogenolysis of dibromocyclohexanetetrols; the hydration of diepoxycyclohexanes; and the hydroxylation of cyclohexadienes or cyclohexenediols.