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.
Is ...
ic
hydrocarbon
In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ...
s 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
In chemistry, a bicyclic molecule () is a molecule that features two joined rings. Bicyclic structures occur widely, for example in many biologically important molecules like α-thujene and camphor. A bicyclic compound can be carbocyclic (all ...
sesquiterpene
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modific ...
s. 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
In military strategy, a bridgehead (or bridge-head) is the strategically important area of ground around the end of a bridge or other place of possible crossing over a body of water which at time of conflict is sought to be defended or taken over ...
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 anti ...
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