Cadinenes are a group of
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
hydrocarbons that occur in a wide variety of
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 o ...
-producing plants. The name is derived from that of the
Cade juniper (''Juniperus oxycedrus'' L.), the wood of which yields an oil from which cadinene isomers were first isolated.
Chemically, the cadinenes are
bicyclic sesquiterpenes. The term ''cadinene'' has sometimes also been used in a broad sense to refer to any sesquiterpene with the so-called cadalane (4-isopropyl-1,6-dimethyldecahydronaphthalene) carbon skeleton. Because of the large number of known double-bond and stereochemical isomers, this class of compounds has been subdivided into four subclasses based on the
relative stereochemistry at the isopropyl group and the two
bridgehead carbon atoms.
[
] The name ''cadinene'' is now properly used only for the first subclass below, which includes the compounds originally isolated from
cade oil. Only one
enantiomer
In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...
of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.
Image:Cadalane.svg, Cadalane skeleton
Image:Cadinane.svg, Cadinane stereochemistry
Image:Muurolane.svg, Muurolane stereochemistry
Image:Amorphane.svg, Amorphane stereochemistry
Image:Bulgarane.svg, Bulgarane stereochemistry
References
{{reflist
Flavors
Sesquiterpenes
Cyclohexenes
Isopropyl compounds