decahydroxycyclopentane
{{Chembox
| Watchedfields = changed
| verifiedrevid = 399891068
| ImageFile = Decahydroxycyclopentane.png
| ImageSize = 150px
| PIN = Cyclopentanedecol
| OtherNames = Decahydroxycyclopentane
|Section1={{Chembox Identifiers
| InChI = 1/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H
| InChIKey = DYYJKUCFQJABMU-UHFFFAOYAO
| SMILES1 = C1(C(C(C(C1(O)O)(O)O)(O)O)(O)O)(O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DYYJKUCFQJABMU-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 595-03-9
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=21477367
| PubChem = 12305029
| SMILES = OC1(O)C(O)(O)C(O)(O)C(O)(O)C(O)1O
}}
|Section2={{Chembox Properties
| C=5|H=10|O=10
| Appearance = Colorless crystals
| Density =
| MeltingPt = {{convert|115|C|F K}} (with dehydration); slow decomposition at about {{convert|160|C|F K}}
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
Decahydroxycyclopentane is an organic compound with formula {{chem2|C5O10H10}} or {{chem2|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" ({{chem2|C5O5*5H2O}}) is now believed to be the decahydroxycyclopentane.
{{cite journal
|title=Oxocarbons and pseudooxocarbons
|author=Gunther Seitz
|author2=Peter Imming
|journal=Chemical Reviews
|year=1992
|volume=92
|issue=6
|pages=1227–1260
|doi=10.1021/cr00014a004
The compound was synthesized by Heinrich Will in 1861, although for a long time it was believed to be a hydrate of {{chem2|C5O5}}. It can be prepared by oxidation of croconic acid {{chem2|C5O3(OH)2}} with nitric acid.{{cite journal | journal = Justus Liebigs Annalen der Chemie | volume = 118 | issue = 2 | title = Beitrag zur Kenntniss der Krokonsäure
| first = H. | last = Will | doi = 10.1002/jlac.18611180204 | pages = 177–187 | year = 1861| url = https://zenodo.org/record/1427165 }} It can be isolated as water-soluble colorless crystals that melt with dehydration at about 115 °C, and slowly decompose at about 160 °C.{{cite journal
|title = Cyclic Polyhydroxy Ketones. I. Oxidation Products of Hexahydroxybenzene (Benzenehexol)
|first = Alexander J.
|last = Fatiadi
|author2 = Horace S. Isbell
|author3 = William F. Sager
|journal = Journal of Research of the National Bureau of Standards Section A
|volume = 67A
|issue = 2
|date = March–April 1963
|url = http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf
|pages = 153–162
|doi = 10.6028/jres.067A.015
|access-date = 2009-03-22
|archive-url = https://web.archive.org/web/20090325204012/http://nvl.nist.gov/pub/nistpubs/jres/067/2/V67.N02.A06.pdf
|archive-date = 2009-03-25
|url-status = dead
|pmid = 31580622
|pmc = 6640573
}}