Decahydroxycyclopentane
Encyclopedia
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.
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
. It can be isolated as water soluble colorless crystals that melt with dehydration at about 115 °C, and slowly decompose at about 160 °C.
Organic compound
An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...
with formula C5O10H10 or C5(OH)10. It is a fivefold geminal
Geminal
In chemistry, the term geminal refers to the relationship between two functional groups that are attached to the same atom...
diol
Diol
A diol or glycol is a chemical compound containing two hydroxyl groups A geminal diol has two hydroxyl groups bonded to the same atom...
on a cyclopentane
Cyclopentane
Cyclopentane is a highly flammable alicyclic hydrocarbon with chemical formula 510 and CAS number 287-92-3, consisting of a ring of five carbon atoms each bonded with two hydrogen atoms above and below the plane. It occurs as a colorless liquid with a petrol-like odor. Its melting point is −94 °C...
backbone.
The compound can be regarded as the fivefold hydrate of cyclopentanepentone
Cyclopentanepentone
Cyclopentanepentone, also known as leuconic acid, is a hypothetical organic compound with formula C5O5, the fivefold ketone of cyclopentane...
. Indeed, the product referred to in the literature and trade as "cyclopentanepentone pentahydrate" (C5O5·5H2O) is now believed to be the decahydroxycyclopentane.
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
Croconic acid
Croconic acid or 4,5-dihydroxycyclopentenetrione is a chemical compound with formula C5H2O5 or 32. It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms...
C5O3(OH)2 with nitric acid
Nitric acid
Nitric acid , also known as aqua fortis and spirit of nitre, is a highly corrosive and toxic strong acid.Colorless when pure, older samples tend to acquire a yellow cast due to the accumulation of oxides of nitrogen. If the solution contains more than 86% nitric acid, it is referred to as fuming...
. It can be isolated as water soluble colorless crystals that melt with dehydration at about 115 °C, and slowly decompose at about 160 °C.