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).

Dodecahydroxycyclohexane

Names
Preferred IUPAC name Cyclohexanedodecol
Other names Dodecahydroxycyclohexane
Identifiers
CAS Number	54890-03-8 Y 13941-78-1 (dihydrate) Y
3D model (JSmol)	Interactive image
ChemSpider	279614 Y
PubChem CID	315987
UNII	I1Z9VS3H64 Y 5BWD2J7B4W (dihydrate) Y
CompTox Dashboard (EPA)	DTXSID90203381
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
SMILES OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
Properties
Chemical formula	(C(OH)2)6
Molar mass	276.150 g·mol−1
Appearance	Colourless crystals (dihydrate)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Dihydrate

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

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 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).

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