Dodecahydroxycyclohexane

Dodecahydroxycyclohexane

Names
IUPAC name cyclohexane-1,1,2,2,3,3,4,4,5,5,6,6-dodecol
Other names dodecahydroxycyclohexane
Identifiers
ChemSpider	279614 Y
InChI InChI=1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H Y Key: MZIPHGCOJCDHPI-UHFFFAOYSA-N Y InChI=1/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H Key: MZIPHGCOJCDHPI-UHFFFAOYAW
Jmol-3D images	Image
PubChem	315987
SMILES OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
UNII	I1Z9VS3H64 Y
Properties
Chemical formula	C6O12H12
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Y verify (what is: Y/N?)
Infobox references

Dodecahydroxycyclohexane is an organic compound with molecular formula C₆O₁₂H₁₂ or C₆(OH)₁₂. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone (C₆O₆).

Dihydrate

The dihydrate C₆O₁₂H₁₂·2H₂O can be crystallized from methanol as colorless plates or prisms, that decompose at about 100 C.^[1]

Thermal ellipsoid model of the molecular cell of dodecahydroxycyclohexane dihydrate

This compound was synthetized by J. Lerch^[2] in 1862 by oxidation of benzenehexol C₆(OH)₆ or tetrahydroxy-p-benzoquinone C₆(OH)₄O₂ 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 (C₆O₆·8H₂O).

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

References