Dodecahydroxycyclohexane

Source: Wikipedia, the free encyclopedia.
Dodecahydroxycyclohexane
Names
Preferred IUPAC name
Cyclohexanedodecol
Other names
Dodecahydroxycyclohexane
Identifiers
3D model (
JSmol
)
ChemSpider
UNII
  • InChI=1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H checkY
    Key: MZIPHGCOJCDHPI-UHFFFAOYSA-N checkY
  • 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
  • OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
Properties
(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).
checkY verify (what is checkY☒N ?)

Dodecahydroxycyclohexane is an

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).

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

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

References

  1. PMID 31580622. Archived from the original
    (PDF) on 2009-03-25. Retrieved 2009-03-22.
  2. doi:10.1002/prac.18620870146
    .
  3. doi:10.1002/cber.188501801110
    .
  4. doi:10.1021/j150553a047
    .
  5. ^ Thomas M. Klapötke; Kurt Polborn; Jan J. Weigand (March 2005). "Dodecahydroxycyclohexane dihydrate" (PDF). Acta Crystallographica E. Archived from the original (PDF) on 2020-03-04.
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