Copaene

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^[1] in 1963. The double-bond isomer with an exo-methylene group, β-copaene, was first reported^[2] in 1967.

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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. Tetrahedron Letters 28, 1933.
2. ^ L. Westfelt, 1967. Acta Chemica Scandinavica 21, 152.
3. ^ R. Nishida et al., 2000. Journal of Chemical Ecology 26, 87.