Decahydroxycyclopentane is an
organic compound
In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...
with formula or . It is a fivefold
geminal
In chemistry, the descriptor geminal () refers to the relationship between two atoms or functional groups that are attached to the same atom. A geminal diol, for example, is a diol (a molecule that has two alcohol functional groups) attached t ...
diol
A diol is a chemical compound containing two hydroxyl groups ( groups). An aliphatic diol is also called a glycol. This pairing of functional groups is pervasive, and many subcategories have been identified.
The most common industrial diol is e ...
on a
cyclopentane
Cyclopentane (also called C pentane) is a highly flammable alicyclic hydrocarbon with chemical formula C5H10 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 occ ...
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.
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
Croconic acid or 4,5-dihydroxycyclopentenetrione is a chemical compound with formula or . It has a cyclopentene backbone with two hydroxyl groups adjacent to the double bond and three ketone groups on the remaining carbon atoms. It is sensitiv ...
with
nitric acid
Nitric acid is the inorganic compound with the formula . It is a highly corrosive mineral acid. The compound is colorless, but older samples tend to be yellow cast due to decomposition into oxides of nitrogen. Most commercially available ni ...
. It can be isolated as water-soluble colorless crystals that melt with dehydration at about 115 °C, and slowly decompose at about 160 °C.
See also
*
Dodecahydroxycyclohexane
Dodecahydroxycyclohexane is an organic chemistry, organic compound with molecular formula or or . It is a sixfold geminal diol with a cyclohexane backbone and can be regarded as a sixfold hydrate of cyclohexanehexone ().
Dihydrate
The dihydrate ...
References
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Cyclitols
Cyclopentanes
Geminal diols