Copaene
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| (−)-α-Copaene | |
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| Chemical name | (1R,2S,6S,7S,8S)-8-isopropyl-1,3- dimethyltricyclo[4.4.0.02,7]dec-3-ene |
| Chemical formula | C15H24 |
| Molecular mass | 204.36 g/mol |
| CAS number | [3856-25-5] |
| Density | 0.910 g/cm3 |
| Melting point | |
| Boiling point | 124 °C (15 mm Hg) |
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| Disclaimer and references | |
| (−)-β-Copaene | |
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| Chemical name | (1R,2S,6S,7S,8S)-8-isopropyl-1-methyl- 3-methylenetricyclo[4.4.0.02,7]decane |
| Chemical formula | C15H24 |
| Molecular mass | 204.36 g/mol |
| CAS number | |
| Density | |
| Melting point | |
| Boiling point | |
| SMILES | |
| 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 in 1963. The double-bond isomer with an exo-methylene group, β-copaene, was first reported 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.
[edit] References
- ↑ 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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