Fenchone is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
classified as a
monoterpenoid and a
ketone
In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...
. It is a colorless oily liquid. It has a structure and an odor similar to those of
camphor
Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the kapu ...
. Fenchone is a constituent of
absinthe and the
essential oil
An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...
of
fennel
Fennel (''Foeniculum vulgare'') is a flowering plant species in the carrot family. It is a hardy, perennial herb with yellow flowers and feathery leaves. It is indigenous to the shores of the Mediterranean but has become widely naturalized ...
. Fenchone is used as a flavor in foods and in perfumery.
[Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; .]
Other names for fenchone include ''dl''-fenchone and (±)-fenchone. It is a mixture of the
enantiomers
In chemistry, an enantiomer (Help:IPA/English, /ɪˈnænti.əmər, ɛ-, -oʊ-/ Help:Pronunciation respelling key, ''ih-NAN-tee-ə-mər''), also known as an optical isomer, antipode, or optical antipode, is one of a pair of molecular entities whi ...
''d''-fenchone and ''l''-fenchone. Other names for ''d''-fenchone include (+)-fenchone and (1''S'',4''R'')-fenchone. Other names for ''l''-fenchone include (−)-fenchone and (1''R'',4''S'')-fenchone. The ''d''-fenchone enantiomer occurs in pure form in
wild,
bitter and
sweet fennel plants and seeds, whereas the ''l''-fenchone enantiomer occurs in pure form in
wormwood,
tansy, and
cedarleaf.
[U. Ravid, E. Putievsky, I. Katzir, R. Ikan “Chiral gc analysis of enantiomerically pure fenchone in essential oils” in Flavour and Fragrance Journal, 7: 169-172, John Wiley & Sons: 1992. Published online: June 1992; .]
References
Absinthe
Cyclic ketones
Monoterpenes
Norbornanes
{{ketone-stub