Dodecahydroxycyclohexane

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
Dodecahydroxycyclohexane
File:Dodecahydroxycyclohexane-2D-skeletal.png
File:Dodecahydroxycyclohexane-from-dihydrate-xtal-CM-3D-ellipsoids.png
File:Sample of cyclohexanehexone octahydrate.jpg
Names
Preferred IUPAC name
Cyclohexanedodecol
Other names
Dodecahydroxycyclohexane
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
UNII
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
  • 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).

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).

Dihydrate

[edit | edit source]

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

File:Dodecahydroxycyclohexane-dihydrate-from-xtal-CM-3D-ellipsoids.png
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

[edit | edit source]

References

[edit | edit source]
  1. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ Lua error in Module:Cite_Q/config at line 10: attempt to index field 'wikibase' (a nil value).
  4. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
Retrieved from "http://70.231.62.181/index.php?title=Dodecahydroxycyclohexane&oldid=14093133"