dodecahydroxycyclohexane
{{Chembox
|verifiedrevid = 443707193
|ImageFile = Dodecahydroxycyclohexane-2D-skeletal.png
|ImageSize = 150px
|ImageFile1 = Dodecahydroxycyclohexane-from-dihydrate-xtal-CM-3D-ellipsoids.png
|ImageSize1 = 200px
|ImageFile2 = Sample of cyclohexanehexone octahydrate.jpg
|PIN = Cyclohexanedodecol
|OtherNames = Dodecahydroxycyclohexane
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 279614
|InChI = 1/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H
|InChIKey = MZIPHGCOJCDHPI-UHFFFAOYAW
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|StdInChI = 1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
|StdInChIKey = MZIPHGCOJCDHPI-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|CAS}}
|CASNo = 54890-03-8
|CASNo1_Ref = {{cascite|correct|CAS}}
|CASNo1 = 13941-78-1
|CASNo1_Comment =(dihydrate)
|PubChem = 315987
|UNII_Ref = {{fdacite|correct|FDA}}
|UNII = I1Z9VS3H64
|UNII1_Ref = {{fdacite|correct|FDA}}
|UNII1 = 5BWD2J7B4W
|UNII1_Comment = (dihydrate)
|SMILES = OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O
}}
|Section2={{Chembox Properties
|Formula = {{chem2|(C(OH)2)6}}
|C=6|O=12|H=12
|Appearance = Colourless crystals (dihydrate)
}}
}}
Dodecahydroxycyclohexane is an organic compound with molecular formula {{chem2|C6O12H12}} or {{chem2|C6(OH)12}} or {{chem2|(C(OH)2)6}}. It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone ({{chem2|C6O6}}).
Dihydrate
The dihydrate {{chem2|C6O12H12*2H2O}} can be crystallized from methanol as colorless plates or prisms, that decomposes at about 100 °C.{{cite journal|title = Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)|author = Alexander J. Fatiadi|author2 = Horace S. Isbell|author3 = William F. Sager|journal = Journal of Research of the National Bureau of Standards Section A|volume = 67A|issue = 2|date = March–April 1963|url = http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf|pages = 153–162|doi = 10.6028/jres.067A.015|access-date = 2009-03-22|archive-url = https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf|archive-date = 2009-03-25|url-status = dead|pmid = 31580622|pmc = 6640573}}
Image:Dodecahydroxycyclohexane-dihydrate-from-xtal-CM-3D-ellipsoids.png model of the molecular cell of dodecahydroxycyclohexane dihydrate]]
This compound was synthesized by Joseph Udo Lerch (1816–1892) in 1862{{cite journal |author=Jos. Ud. Lerch |year=1862 |title=Ueber Kohlenoxydkalium und die aus demselben darstellbaren Säuren |url=https://zenodo.org/record/1427832 |journal=Journal für Praktische Chemie |volume=87 |issue=1 |pages=427–469 |doi=10.1002/prac.18620870146}} by oxidation of benzenehexol {{chem2|C6(OH)6}} or tetrahydroxy-p-benzoquinone {{chem2|C6(OH)4O2}} and characterized by Rudolf Nietzki and {{Ill|Theodor Benckiser|de}} in 1885,{{Cite Q|Q56853054}} although the product was for a long time assumed to be hexaketocyclohexane with water of crystallization ({{chem2|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,{{cite journal|author = Willis B. Person and Dale G. Williams|year = 1957|title = Infrared spectra and the structures of leuconic acid and triquinoyl|journal = J. Phys. Chem.|volume = 61|issue = 7|pages = 1017–1018|doi = 10.1021/j150553a047}} but was confirmed by X-ray diffraction analysis only in 2005.{{cite journal|title = Dodecahydroxycyclohexane dihydrate|author = Thomas M. Klapötke|author2 = Kurt Polborn|author3 = Jan J. Weigand|journal = Acta Crystallographica E|url = http://journals.iucr.org/e/issues/2005/05/00/ob6498/ob6498.pdf|archive-url = https://web.archive.org/web/20200304115045/http://journals.iucr.org/e/issues/2005/05/00/ob6498/ob6498.pdf|url-status = dead|archive-date = 2020-03-04|date = March 2005}}