Copaene

Title: Copaene
CAS Registry Number: 3856-25-5
CAS Name: [1R-(1a,2a,6a,7a,8a)]-1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02,7]dec-3-ene
Additional Names: (1R,2S,6S,7S,8S)-(-)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.02,7]dec-3-ene; a-copaene
Molecular Formula: C15H24
Molecular Weight: 204.35
Percent Composition: C 88.16%, H 11.84%
Literature References: Tricyclic sesquiterpene occurring in African copaiba balsam oil; in the so-called supa oil from Sindora supa Merr. (S. wallichii F.-Vill.), Leguminosae: Henderson et al., J. Chem. Soc. 1926, 3077. Also in the essential oil of Phyllocladus trichomanoides D. Don, Podocarpaceae: Briggs, Sutherland, J. Org. Chem. 13, 1 (1948); from Cyperus articulatus Michx., Cyperaceae: Couchman et al., Tetrahedron 20, 2037 (1964). Structural studies: Kapadia et al., ibid. 21, 607 (1965). Absolute stereostructure: deMao et al., ibid. 619. Synthesis: Heathcock, J. Am. Chem. Soc. 88, 4110 (1966); Heathcock et al., ibid. 89, 4133 (1967); Corey, Watt, ibid. 95, 2303 (1973). Review: J. Simonsen, D. H. R. Barton, The Terpenes vol. III (University Press, Cambridge, 1952) pp 88-91. See also Ylangene.
Properties: Oily liquid, bp 246-251°; bp10 119-120°; d1515 0.9077; nD20 1.4894. [a]D22 -6.3° (c = 1.20 in chloroform).
Boiling point: bp 246-251°; bp10 119-120°
Optical Rotation: [a]D22 -6.3° (c = 1.20 in chloroform)
Index of refraction: nD20 1.4894
Density: d1515 0.9077
Copaiba Copal Coparaffinate Copper Phthalocyanine Copper(I) Thiophene-2-carboxylate

Copaene
α-copaene
(-)-α-Copaene
β-copaene
(-)-β-Copaene
Identifiers
CAS number 3856-25-5 (α) YesY
ChemSpider 10231594 (α) YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H24
Molar mass 204.35 g mol−1
Density 0.939 g/mL
Boiling point 124 °C (15 mmHg)
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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]