Decahydroxycyclopentane Explained

Decahydroxycyclopentane is an organic compound with formula or . 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" 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 . It can be prepared by oxidation of croconic acid 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

• Dodecahydroxycyclohexane

Notes and References

1. Oxocarbons and pseudooxocarbons . Gunther Seitz . Peter Imming . Chemical Reviews . 1992 . 92 . 6 . 1227–1260 . 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 . 10.1021/j150553a047 .
3. Justus Liebigs Annalen der Chemie . 118 . 2 . Beitrag zur Kenntniss der Krokonsäure. H. . Will . 10.1002/jlac.18611180204 . 177 - 187 . 1861.
4. Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol) . Alexander J. . Fatiadi . Horace S. Isbell . William F. Sager . Journal of Research of the National Bureau of Standards Section A . 67A . 2 . March–April 1963 . 153 - 162 . 10.6028/jres.067A.015 . 2009-03-22 . https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf . 2009-03-25 . dead . 31580622 . 6640573.