Jasmone 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 ...
, which is a volatile portion of the oil from
jasmine
Jasmine ( taxonomic name: ''Jasminum''; , ) is a genus of shrubs and vines in the olive family (Oleaceae). It contains around 200 species native to tropical and warm temperate regions of Eurasia, Africa, and Oceania. Jasmines are widely cultiva ...
flowers. It is a colorless to pale yellow liquid. Jasmone can exist in two
isomer
In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers.
Iso ...
ic forms with differing geometry around the pentenyl double bond, ''cis''-jasmone and ''trans''-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture of both, with the cis form predominating. Both forms have similar odors and chemical properties. Its structure was deduced by
Lavoslav Ružička.
Jasmone is produced by some plants by the metabolism of
jasmonic acid, via a
decarboxylation
Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO2). Usually, decarboxylation refers to a reaction of carboxylic acids, removing a carbon atom from a carbon chain. The reverse process, which is t ...
.
[Paulina Dąbrowska, Wilhelm Boland "iso-OPDA: An Early Precursor of cis-Jasmone in Plants?" ChemBioChem 2007, Volume 8, pages 2281–2285. ] It can act as either an attractant or a repellent for various insects. Commercially jasmone is used primarily in perfumes and cosmetics.
References
{{reflist
Enones
Cyclopentenes