Copaene

(-)-α-Copaene (top)
(-)-β-Copaene (bottom)
IUPAC name

(1R,2S,6S,7S,8S)-8-isopropyl-1,3-
dimethyltricyclo[4.4.0.02,7]dec-3-ene
Identifiers
CAS number 3856-25-5 Y
ChemSpider 10231594 Y
Jmol-3D images Image 1
Properties
Molecular formula C15H24
Molar mass 204.36 g/mol
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Copaene, or more precisely, α-copaene, is the common (or trivial) chemical name of an oily liquid hydrocarbon that is found in a number of essential oil-producing plants. The name is derived from that of the resin-producing tropical copaiba tree, Copaifera langsdorfii, from which the compound was first isolated in 1914. Its structure, including the chirality, was determined in 1963.[1] The double-bond isomer with an exo-methylene group, β-copaene, was first reported in 1967.[2]

Chemically, the copaenes are tricyclic sesquiterpenes. The molecules are chiral, and the α-copaene enantiomer most commonly found in higher plants exhibits a negative optical rotation of about −6°. The rare (+)-α-copaene is also found in small amounts in some plants. It is of economic significance because it is strongly attracting to an agricultural pest, the Mediterranean fruit fly Ceratitis capitata.[3]

References

  1. ^ V.H. Kapadia et al. (1963). "Structure of mustakone and copaene". Tetrahedron Letters 28 (28): 1933. doi:10.1016/S0040-4039(01)90945-1. 
  2. ^ L. Westfelt; Westfelt, Lars; Sky, K.; Nilsson, Åke; Theorell, H.; Blinc, R.; Paušak, S.; Ehrenberg, L. et al. (1967). "Beta-Copaene and beta-Ylangene, Minor Sesquiterpenes of the Wood of Pinus silvestris L. And of Swedish Sulphate Turpentine". Acta Chemica Scandinavica 21: 152. doi:10.3891/acta.chem.scand.21-0152. 
  3. ^ R. Nishida et al. (2000). Journal of Chemical Ecology 26: 87. doi:10.1023/A:1005489411397.