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Decahydroxycyclopentane
Decahydroxycyclopentane.png
IUPAC name
Other names decahydroxycyclopentane
Identifiers
CAS number 595-03-9
SMILES
Properties
Molecular formula C5H10O10
Molar mass 230.13 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

The compound can be regarded as the five-fold 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]

[edit] References

  1. ^ Gunther Seitz; Peter Imming (1992). "Oxocarbons and pseudooxocarbons". Chemical Reviews 92 (6): 1227-1260. doi:10.1021/cr00014a004. http://admin.pubs.acs.org/doi/pdf/10.1021/cr00014a004. 
  2. ^ 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
  3. ^ Will, H.. "Beitrag zur Kenntniss der Krokonsäure". Justus Liebigs Annalen der Chemie 118 (2). 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)". Journal of Research of the National Bureau of Standards A: Physics and Chemistry 67A (2): 153–162. http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf. 

[edit] See also




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