Decahydroxycyclopentane

Decahydroxycyclopentane
Names
	IUPAC name cyclopentane-1,1,2,2,3,3,4,4,5,5-decaol
	Other names decahydroxycyclopentane
Identifiers
CAS Number	595-03-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	21477367 ;
PubChem CID	12305029;
CompTox Dashboard (EPA)	DTXSID30486717 ;
	InChI InChI=1S/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H Key: DYYJKUCFQJABMU-UHFFFAOYSA-N ; InChI=1/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H Key: DYYJKUCFQJABMU-UHFFFAOYAO;
	SMILES OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)1O; C1(C(C(C(C1(O)O)(O)O)(O)O)(O)O)(O)O;
Properties
Chemical formula	C5H10O10
Molar mass	230.125 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Decahydroxycyclopentane is an organic compound with formula C₅O₁₀H₁₀ or C₅(OH)₁₀. It is a fivefold geminal diol on a cyclopentane backbone.

The compound can be regarded as the fivefold hydrate of cyclopentanepentone. Indeed, the product referred to in the literature and trade as "cyclopentanepentone pentahydrate" (C₅O₅·5H₂O) is now believed to be the decahydroxycyclopentane.[1][2]

The compound was synthetized by Heinrich Will in 1861, although for a long time it was believed to be a hydrate of C₅O₅. It can be prepared by oxidation of croconic acid C₅O₃(OH)₂ with nitric acid.[3] It can be isolated as water-soluble colorless crystals that melt with dehydration at about 115 °C, and slowly decompose at about 160 °C.[4]

References

Gunther Seitz; Peter Imming (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.
Person, Willis B.; Williams, Dale G. (1957). "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem. 61 (7): 1017–1018. doi:10.1021/j150553a047.
Will, H. (1861). "Beitrag zur Kenntniss der Krokonsäure". Justus Liebigs Annalen der Chemie. 118 (2): 177–187. doi:10.1002/jlac.18611180204.
Fatiadi, Alexander J.; 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.

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[1] Gunther Seitz; Peter Imming (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews. 92 (6): 1227–1260. doi:10.1021/cr00014a004.

[2] Person, Willis B.; Williams, Dale G. (1957). "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem. 61 (7): 1017–1018. doi:10.1021/j150553a047.

[3] Will, H. (1861). "Beitrag zur Kenntniss der Krokonsäure". Justus Liebigs Annalen der Chemie. 118 (2): 177–187. doi:10.1002/jlac.18611180204.

[4] Fatiadi, Alexander J.; 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.

Decahydroxycyclopentane

See also

References