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 langsdorffii, 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 exocyclic-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. (+)-α-copaene is of economic significance because it is strongly attracting to an agricultural pest, the Mediterranean fruit fly Ceratitis capitata.[3]
References
^V.H. Kapadia; Nagasampagi, B.A.; Naik, V.G.; Dev, Sukh; et al. (1963). "Structure of mustakone and copaene". Tetrahedron Letters. 4 (28): 1933. doi:10.1016/S0040-4039(01)90945-1.
^R. Nishida; Shelly, Todd E.; Whittier, Timothy S.; Kaneshiro, Kenneth Y.; et al. (2000). "α-Copaene, A Potential Rendezvous Cue for the Mediterranean Fruit Fly, Ceratitis Capitata?". Journal of Chemical Ecology. 26: 87. doi:10.1023/A:1005489411397. S2CID44000579.
