Copaene
| (−)-β-Copaene |
|
|
| IUPAC name |
(1R,2S,6S,7S,8S)-8-isopropyl-1,3-
dimethyltricyclo[4.4.0.02,7]dec-3-ene |
| Properties |
| Molecular formula |
C15H24 |
| Molar mass |
204.36 g/mol |
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and 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[1] in 1963. The double-bond isomer with an exo-methylene group, β-copaene, was first reported[2] in 1967.
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
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The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking. |
- ^ V.H. Kapadia et al., 1963. Tetrahedron Letters 28, 1933.
- ^ L. Westfelt, 1967. Acta Chemica Scandinavica 21, 152.
- ^ R. Nishida et al., 2000. Journal of Chemical Ecology 26, 87.
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