2-Hydroxy-3-methyl-2-cyclopenten-1-one 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. The ...
related to
1,2-cyclopentanedione. It is the
enol
In organic chemistry, alkenols (shortened to enols) are a type of reactive structure or intermediate in organic chemistry that is represented as an alkene ( olefin) with a hydroxyl group attached to one end of the alkene double bond (). The te ...
tautomer
Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert.
The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...
of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound is often called methylcyclopentenolone. It is a colorless solid.
Synthesis and structure
The compound is prepared by base-catalyzed condensation of
1‐hydroxyhexane‐2,5‐dione, a derivative of
hydroxymethylfurfural
Hydroxymethylfurfural (HMF), also 5-(hydroxymethyl)furfural, is an organic compound formed by the dehydration of reducing sugars. It is a white low-melting solid (although commercial samples are often yellow) which is highly soluble in both water ...
.
[
The structure has been confirmed by ]X-ray crystallography
X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...
.
Use and occurrence
It is one of many products from the pyrolysis
The pyrolysis (or devolatilization) process is the thermal decomposition of materials at elevated temperatures, often in an inert atmosphere. It involves a change of chemical composition. The word is coined from the Greek-derived elements ''py ...
of lignocellulose
Lignocellulose refers to plant dry matter (biomass), so called lignocellulosic biomass. It is the most abundantly available raw material on the Earth for the production of biofuels. It is composed of two kinds of carbohydrate polymers, cellulose a ...
.
It is used in flavors and perfumery for its maple
''Acer'' () is a genus of trees and shrubs commonly known as maples. The genus is placed in the family Sapindaceae.Stevens, P. F. (2001 onwards). Angiosperm Phylogeny Website. Version 9, June 2008 nd more or less continuously updated since http ...
- or caramel
Caramel ( or ) is an orange-brown confectionery product made by heating a range of sugars. It can be used as a flavoring in puddings and desserts, as a filling in bonbons, or as a topping for ice cream and custard.
The process of caramelizatio ...
-like odor. It contributes to the flavor or odor of many foods including wines, coffee, paprika, and salmon. It is sometimes called maple lactone because it occurs in maple syrup
Maple syrup is a syrup made from the sap of maple trees. In cold climates, these trees store starch in their trunks and roots before winter; the starch is then converted to sugar that rises in the sap in late winter and early spring. Maple tree ...
(it is not, however, a lactone
Lactones are cyclic carboxylic esters, containing a 1-oxacycloalkan-2-one structure (), or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring.
Lactones are formed by intramolecular esterification of the co ...
).
See also
* 1,2-Cyclopentanedione
References
{{DEFAULTSORT:Hydroxy-3-methyl-2-cyclopenten-1-one, 2-
Diketones
Cyclopentanes