Chemistry:Decahydroxycyclopentane

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Decahydroxycyclopentane
Decahydroxycyclopentane.png
Names
Preferred IUPAC name
Cyclopentanedecol
Other names
Decahydroxycyclopentane
Identifiers
3D model (JSmol)
ChemSpider
Properties
C5H10O10
Molar mass 230.125 g·mol−1
Appearance Colorless crystals
Melting point 115 °C (239 °F; 388 K) (with dehydration); slow decomposition at about 160 °C (320 °F; 433 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Decahydroxycyclopentane is an organic compound with formula C
5
O
10
H
10
or C
5
(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" (C
5
O
5
 · 5H2O
) is now believed to be the decahydroxycyclopentane.[1][2]

The compound was synthesized by Heinrich Will in 1861, although for a long time it was believed to be a hydrate of C
5
O
5
. It can be prepared by oxidation of croconic acid C
5
O
3
(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]

See also

References

  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. https://zenodo.org/record/1427165. 
  4. Fatiadi, Alexander J.; Horace S. Isbell; William F. Sager (March–April 1963). "Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)". Journal of Research of the National Bureau of Standards Section A 67A (2): 153–162. doi:10.6028/jres.067A.015. PMID 31580622. PMC 6640573. http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf. Retrieved 2009-03-22.