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Cadinenes are a group of isomeric
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-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 modificat ...
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 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