Decahydroxycyclopentane
title: "Decahydroxycyclopentane" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cyclitols", "cyclopentanes", "geminal-diols"] topic_path: "general/cyclitols" source: "https://en.wikipedia.org/wiki/Decahydroxycyclopentane" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0
| 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 = | StdInChI = 1S/C5H10O10/c6-1(7)2(8,9)4(12,13)5(14,15)3(1,10)11/h6-15H | StdInChIKey_Ref = | StdInChIKey = DYYJKUCFQJABMU-UHFFFAOYSA-N | CASNo_Ref = | CASNo = 595-03-9 | ChemSpiderID_Ref = | 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 = 115 C (with dehydration); slow decomposition at about 160 C | BoilingPt = | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }}
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. |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 . It can be prepared by oxidation of croconic acid 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
References
References
- (1957). "Infrared spectra and the structures of leuconic acid and triquinoyl". J. Phys. Chem..
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