Dodecahydroxycyclohexane

Dodecahydroxycyclohexane
IUPAC name cyclohexane-1,1,2,2,3,3,4,4,5,5,6,6-dodecol
Other names dodecahydroxycyclohexane
Identifiers
PubChem	315987
ChemSpider	279614 Y
UNII	I1Z9VS3H64
Jmol-3D images	Image 1
SMILES OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
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
Properties
Molecular formula	C6O12H12
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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

1. ^ Alexander J. Fatiadi; Horace S. Isbell, William F. Sager (March-April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)". Journal of Research of the National Bureau of Standards A: Physics and Chemistry 67A (2): 153–162. http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf. 
2. ^ Jos. Ud. Lerch (1862). "Ueber Kohlenoxydkalium und die aus demselben darstellbaren Säuren". Journal für Praktische Chemie 87 (1): 427–469. doi:10.1002/prac.18620870146. 
3. ^ R. Nietzki, Th. Benckiser (1885). "Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure". Berichte der deutschen chemischen Gesellschaft 18 (1): 499–515. doi:10.1002/cber.188501801110. 
4. ^ Willis B. Person and Dale G. Williams (1957). "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem. 61 (7): 1017–1018. doi:10.1021/j150553a047. 
5. ^ Thomas M. Klapötke; Kurt Polborn and Jan J. Weigand (March 2005). "Dodecahydroxycyclohexane dihydrate". Acta Crystallographica E. http://journals.iucr.org/e/issues/2005/05/00/ob6498/ob6498.pdf.