Decahydroxycyclopentane
Watchedfieldschanged
Verifiedrevid399891068
PinCyclopentanedecol
OthernamesDecahydroxycyclopentane

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 synthesized 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]

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
  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. PMC 6640573. PMID 31580622. Archived from the original on 2009-03-25. Retrieved 2009-03-22.