Cadinene is the trivial chemical name of a number of
isomerIn chemistry, isomers are compounds with the same molecular formula but different structural formulas. Isomers do not necessarily share similar properties, unless they also have the same functional groups. There are many different classes of isomers, like stereoisomers, enantiomers, geometrical...
ic
hydrocarbonIn organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons from which one hydrogen atom has been removed are functional groups, called hydrocarbyls....
s that occur in a wide variety of
essential oilAn essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
-producing plants. The name is derived from that of the
Cade juniper (Juniperus oxycedrus L.)Juniperus oxycedrus is a species of juniper, native across the Mediterranean region from Morocco and Portugal, north to southern France, east to westernmost Iran, and south to Lebanon and Israel, growing on a variety of rocky sites from sea level up...
, the wood of which yields an oil from which cadinene isomers were first isolated.
Chemically, the cadinenes are
bicyclicA bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.Fusion of the rings can occur in three ways:...
sesquiterpeneSesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations...
s. The term “cadinene” has sometimes 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 stereochemistryStereochemistry, a subdiscipline of chemistry, involves the study of the relative spatial arrangement of atoms within molecules. An important branch of stereochemistry is the study of chiral molecules....
at the isopropyl group and the two
bridgeheadA bicyclic molecule is a molecule that features two fused rings. Bicyclic molecules occur widely in organic and inorganic compounds.Fusion of the rings can occur in three ways:...
carbon atoms. The name
cadinene is now properly used only for the first subclass below, which includes the compounds originally isolated from
cade oilJuniperus oxycedrus is a species of juniper, native across the Mediterranean region from Morocco and Portugal, north to southern France, east to westernmost Iran, and south to Lebanon and Israel, growing on a variety of rocky sites from sea level up...
. Only one
enantiomerIn chemistry, an enantiomer is one of two stereoisomers that are mirror images of each other that are non-superposable , much as one's left and right hands are the same except for opposite orientation. It can be clearly understood if you try to place your hands one over the other without...
of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.