Decahydroxycyclopentane

Decahydroxycyclopentane
IUPAC name cyclopentane-1,1,2,2,3,3,4,4,5,5-decaol
Other names decahydroxycyclopentane
Identifiers
CAS number	595-03-9
ChemSpider	21477367 Y
Jmol-3D images	Image 1 Image 2
SMILES 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
InChI InChI=1S/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H Y Key: DYYJKUCFQJABMU-UHFFFAOYSA-N Y InChI=1/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H Key: DYYJKUCFQJABMU-UHFFFAOYAO
Properties
Molecular formula	C5H10O10
Molar mass	230.13 g mol−1
Y (verify) (what is: Y/N?) 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 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 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]

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. (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 A: Physics and Chemistry 67A (2): 153–162. http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf. 

See also

• Dodecahydroxycyclohexane