Copaene: Difference between revisions

| verifiedrevid = 401966282

| Name=(-)-α-Copaene <small>(top)</small><br>(-)-β-Copaene <small>(bottom)</small>

| ImageFile = Alpha copaene minus.png

| ImageName = α-copaene

| ImageFile1 = Beta copaene.png

| ImageName1 = β-copaene

| IUPACName = (1''R'',2''S'',6''S'',7''S'',8''S'')-8-isopropyl-1,3-<br />dimethyltricyclo[4.4.0.0^2,7]dec-3-ene

| Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| CASNo= 3856-25-5

| SMILES = CC(C)[C@@H]1CC[C@@]3(C)[C@@H]2C(/C)=C\C[C@H]3[C@H]12

| Section2 = {{Chembox Properties

| Formula = C₁₅H₂₄

| MolarMass = 204.36 g/mol

| Density = 0.910 g/cm³

| MeltingPt =

| BoilingPt = 124 °C (15 mm Hg)

| MolarMass = 204.36 g/mol

| Density =

| MeltingPt =

| BoilingPt =

'''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 (chemistry)|chirality]], was determined in 1963.<ref>{{cite journal | author= V.H. Kapadia ''et al.'' |year=1963 |journal=Tetrahedron Letters | volume=28 | pages=1933 | doi= 10.1016/S0040-4039(01)90945-1 | title= Structure of mustakone and copaene | issue= 28}}</ref> The double-bond isomer with an [[exo-methylene]] group, β-copaene, was first reported in 1967.<ref>{{cite journal | author=L. Westfelt |year=1967| journal=Acta Chemica Scandinavica|volume =21 |pages=152 | doi=10.3891/acta.chem.scand.21-0152 | title=Beta-Copaene and beta-Ylangene, Minor Sesquiterpenes of the Wood of Pinus silvestris L. And of Swedish Sulphate Turpentine | last2=Westfelt | first2=Lars | last3=Sky | first3=K. | last4=Nilsson | first4=Åke | last5=Theorell | first5=H. | last6=Blinc | first6=R. | last7=Paušak | first7=S. | last8=Ehrenberg | first8=L. | last9=Dumanović | first9=J.}}</ref>

Chemically, the copaenes are tricyclic [[terpene|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]]''.<ref>{{Cite journal|author = R. Nishida ''et al.'' |year=2000 |journal=Journal of Chemical Ecology |volume=26|pages=87|doi = 10.1023/A:1005489411397}}</ref>

[[Category:Alkenes]]