Decahydroxycyclopentane

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

Decahydroxycyclopentane
Names
Preferred IUPAC name
Cyclopentanedecol
Other names
Decahydroxycyclopentane
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H checkY
    Key: DYYJKUCFQJABMU-UHFFFAOYSA-N checkY
  • InChI=1/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H
    Key: DYYJKUCFQJABMU-UHFFFAOYAO
  • 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
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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Infobox references

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)" (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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