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{{Chembox |
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{{Chembox |
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| verifiedrevid = 398793137 |
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|verifiedrevid = 443707193 |
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| ImageFile = Dodecahydroxycyclohexane-2D-skeletal.png |
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|ImageFile = Dodecahydroxycyclohexane-2D-skeletal.png |
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| ImageSize = 150px |
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|ImageSize = 150px |
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| ImageFile1 = Dodecahydroxycyclohexane-from-dihydrate-xtal-CM-3D-ellipsoids.png |
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|ImageFile1 = Dodecahydroxycyclohexane-from-dihydrate-xtal-CM-3D-ellipsoids.png |
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| ImageSize1 = 200px |
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|ImageSize1 = 200px |
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|ImageFile2 = Sample of cyclohexanehexone octahydrate.jpg |
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| IUPACName = cyclohexane-1,1,2,2,3,3,4,4,5,5,6,6-dodecol |
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|PIN = Cyclohexanedodecol |
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| OtherNames = dodecahydroxycyclohexane |
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|OtherNames = Dodecahydroxycyclohexane |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 279614 |
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|ChemSpiderID = 279614 |
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| InChI = 1/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H |
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|InChI = 1/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H |
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| InChIKey = MZIPHGCOJCDHPI-UHFFFAOYAW |
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|InChIKey = MZIPHGCOJCDHPI-UHFFFAOYAW |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H |
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|StdInChI = 1S/C6H12O12/c7-1(8)2(9,10)4(13,14)6(17,18)5(15,16)3(1,11)12/h7-18H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MZIPHGCOJCDHPI-UHFFFAOYSA-N |
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|StdInChIKey = MZIPHGCOJCDHPI-UHFFFAOYSA-N |
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| CASNo = |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| PubChem = 315987 |
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| UNII = I1Z9VS3H64 |
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|CASNo = 54890-03-8 |
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|CASNo1_Ref = {{cascite|correct|CAS}} |
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| SMILES = OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O |
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|CASNo1 = 13941-78-1 |
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|CASNo1_Comment =(dihydrate) |
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|PubChem = 315987 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = I1Z9VS3H64 |
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|UNII1_Ref = {{fdacite|correct|FDA}} |
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|UNII1 = 5BWD2J7B4W |
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|UNII1_Comment = (dihydrate) |
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|SMILES = OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>6</sub>O<sub>12</sub>H<sub>12</sub> |
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|Formula = {{chem2|(C(OH)2)6}} |
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|C=6|O=12|H=12 |
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| MolarMass = |
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| Appearance = |
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|Appearance = Colourless crystals (dihydrate) |
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| Density = |
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| MeltingPt = |
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| BoilingPt = |
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| Solubility = }} |
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| Section3 = {{Chembox Hazards |
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| MainHazards = |
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| FlashPt = |
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| Autoignition = }} |
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}} |
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}} |
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}} |
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'''Dodecahydroxycyclohexane''' is an ] compound with ] C<sub>6</sub>O<sub>12</sub>H<sub>12</sub> or C<sub>6</sub>(OH)<sub>12</sub>. It is a sixfold ] ] with a ] backbone and can be regarded as a sixfold ] of ] (C<sub>6</sub>O<sub>6</sub>). |
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'''Dodecahydroxycyclohexane''' is an ] compound with ] {{chem2|C6O12H12}} or {{chem2|C6(OH)12}} or {{chem2|(C(OH)2)6}}. It is a sixfold ] ] with a ] backbone and can be regarded as a sixfold ] of ] ({{chem2|C6O6}}). |
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==Dihydrate== |
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==Dihydrate== |
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The dihydrate {{chem2|C6O12H12*2H2O}} can be crystallized from ] as colorless plates or prisms, that decomposes at about 100 °C.<ref>{{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}}</ref> |
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The dihydrate C<sub>6</sub>O<sub>12</sub>H<sub>12</sub>·2H<sub>2</sub>O can be crystallized from ] as colorless plates or prisms, that decompose at about 100 C. <ref> |
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{{cite journal |
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| title = Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol) |
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| author = Alexander J. Fatiadi |
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| coauthors = Horace S. Isbell, William F. Sager |
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| journal = Journal of Research of the National Bureau of Standards A: Physics and Chemistry |
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| volume = 67A |
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| issue = 2 |
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| month = March-April |
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| url = http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf |
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| year = 1963 |
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| pages = 153–162 |
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}}</ref> |
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] model of the molecular cell of dodecahydroxycyclohexane dihydrate]] |
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] model of the molecular cell of dodecahydroxycyclohexane dihydrate]] |
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This compound was synthesized by ] (1816–1892) in 1862<ref>{{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}}</ref> by oxidation of ] {{chem2|C6(OH)6}} or ] {{chem2|C6(OH)4O2}} and characterized by ] and {{Ill|Theodor Benckiser|de}} in 1885,<ref>{{Cite Q|Q56853054}}</ref> although the product was for a long time assumed to be hexaketocyclohexane with ] ({{chem2|C6O6*8H2O}}). |
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This compound was synthetized by ]<ref> |
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{{cite journal |
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| title = Ueber Kohlenoxydkalium und die aus demselben darstellbaren Säuren |
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| author = Jos. Ud. Lerch |
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| journal = Journal für Praktische Chemie |
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| volume = 87 |
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| issue = 1 |
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| doi = 10.1002/prac.18620870146 |
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| year = 1862 |
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| pages = 427–469 |
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}}</ref> in 1862 by oxidation of ] C<sub>6</sub>(OH)<sub>6</sub> or ] C<sub>6</sub>(OH)<sub>4</sub>O<sub>2</sub> and characterized by ] and others in 1885 <ref> |
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{{cite journal |
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| title = Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure |
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| author = R. Nietzki, Th. Benckiser |
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| journal = Berichte der deutschen chemischen Gesellschaft |
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| volume = 18 |
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| issue = 1 |
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| doi = 10.1002/cber.188501801110 |
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| year = 1885 |
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| pages = 499–515 |
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}}</ref>, although the product was for a long time assumed to be hexaketocyclohexane with ] (C<sub>6</sub>O<sub>6</sub>·8H<sub>2</sub>O). |
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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 <ref> |
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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,<ref>{{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}}</ref> but was confirmed by ] analysis only in 2005.<ref>{{cite journal|title = Dodecahydroxycyclohexane dihydrate|author = ]|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}}</ref> |
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{{cite journal |
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| author = Willis B. Person and Dale G. Williams |
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| year = 1957 |
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| title = Infrared spectra and the structures of leuconic acid and triquinoyl |
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| journal = J. Phys. Chem. |
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| volume = 61 |
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| issue = 7 |
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| pages = 1017–1018 |
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| doi = 10.1021/j150553a047 |
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}}</ref>, but was confirmed by ] analysis only in 2005<ref> |
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{{cite journal |
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| title = Dodecahydroxycyclohexane dihydrate |
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| author = Thomas M. Klapötke |
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| coauthors = Kurt Polborn and Jan J. Weigand |
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| journal = Acta Crystallographica E |
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| url = http://journals.iucr.org/e/issues/2005/05/00/ob6498/ob6498.pdf |
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| month = March |
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| year = 2005 |
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}}</ref> |
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==See also== |
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==See also== |
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* ] |
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*] |
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==References== |
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==References== |
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{{Reflist}} |
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{{Reflist}} |
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