Cadinene

Cadinenes

α-cadinene α-Cadinene
100px γ-Cadinene
100px δ-Cadinene
Names
IUPAC names · (1S,4aR,8aR)-4,7-dimethyl-1-(propan-2-yl)- 1,2,4a,5,6,8a-hexahydronaphthalene (α-cadinene) · (1S,4aR,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene (γ-cadinene) · (1S,8aR)-4,7-dimethyl-1-(propan-2-yl)-1,2,3,5,6,8a-hexahydronaphthalene (δ-cadinene)
Identifiers
CAS Number	24406-05-1 (α-cadinene) Y 39029-41-9 (γ-cadinene) Y 483-76-1 (δ-cadinene) Y
Properties
Chemical formula	C15H24
Molar mass	204.36 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cadinene is the trivial chemical name of a number of isomeric hydrocarbons 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 sesquiterpenes. 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 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 of each subclass is depicted, with the understanding that the other enantiomer bears the same subclass name.

• Cadalane.svg

  Cadalane skeleton

• Cadinane.svg

  Cadinene stereochemistry

• Muurolane.svg

  Muurolene stereochemistry

• Amorphane.svg

  Amorphene stereochemistry

• Bulgarane.svg

  Bulgarene stereochemistry