Dodecahydroxycyclohexane

Dodecahydroxycyclohexane
Names
	Preferred IUPAC name Cyclohexanedodecol
	Other names Dodecahydroxycyclohexane
Identifiers
CAS Number	54890-03-8 ; 13941-78-1 (dihydrate) ;
3D model (JSmol)	Interactive image;
ChemSpider	279614 ;
PubChem CID	315987;
UNII	I1Z9VS3H64 ; 5BWD2J7B4W (dihydrate) ;
CompTox Dashboard (EPA)	DTXSID90203381 ;
	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 Key: MZIPHGCOJCDHPI-UHFFFAOYSA-N ; 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;
	SMILES OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)(O)C1(O)O;
Properties
Chemical formula	(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). verify (what is ?) Infobox references

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

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

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]

References

^ Alexander J. Fatiadi; Horace S. Isbell; William F. Sager (March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)" (PDF). Journal of Research of the National Bureau of Standards Section A. 67A (2): 153–162. doi:10.6028/jres.067A.015. PMC 6640573. PMID 31580622. Archived from the original (PDF) on 2009-03-25. Retrieved 2009-03-22.
^ 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.
^ R. Nietzki; Th. Benckiser (1885). "Ueber Hexaoxybenzolderivate und ihre Beziehungen zur Krokonsäure und Rhodizonsäure". Berichte der Deutschen Chemischen Gesellschaft (in German). 18 (1): 499–515. doi:10.1002/CBER.188501801110. ISSN 0365-9496. Wikidata Q56853054.
^ 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.
^ 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.

[1] Alexander J. Fatiadi; Horace S. Isbell; William F. Sager (March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)" (PDF). Journal of Research of the National Bureau of Standards Section A. 67A (2): 153–162. doi:10.6028/jres.067A.015. PMC 6640573. PMID 31580622. Archived from the original (PDF) on 2009-03-25. Retrieved 2009-03-22.

[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 (in German). 18 (1): 499–515. doi:10.1002/CBER.188501801110. ISSN 0365-9496. Wikidata Q56853054.

[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; Jan J. Weigand (March 2005). "Dodecahydroxycyclohexane dihydrate" (PDF). Acta Crystallographica E. Archived from the original (PDF) on 2020-03-04.

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Dihydrate

See also

References