“Copaene”的意思、由来-开放百科全书

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| PubChem = 70678558
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| PubChem1 = 57339298
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| InChI = 1/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m0/s1
| InChI_Comment = (α)
| InChIKey = VLXDPFLIRFYIME-BTFPBAQTBX
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| StdInChI = 1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m0/s1
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| StdInChIKey = VLXDPFLIRFYIME-BTFPBAQTSA-N
| CASNo_Ref = {{cascite|changed|CAS}}
| CASNo = 3856-25-5
| CASNo_Comment = (α)
| CASNo1_Ref = {{cascite|changed|CAS}}
| CASNo1 = 317819-78-6
| CASNo1_Comment = (β)
| UNII_Ref = {{fdacite|changed|FDA}}
| UNII = 0V56HXQ8N5
| UNII_Comment = (α)
| UNII1_Ref = {{fdacite|changed|FDA}}
| UNII1 = FDX76373XC
| UNII1_Comment = (β)
| EC_number = 223-364-4
| ChEBI = 10221
| ChEBI_Comment = (α)
| ChEBI1 = 64799
| ChEBI1_Comment = (β)
| SMILES = CC(C)[C@@H]1CC[C@@]3(C)[C@@H]2C(/C)=C\\C[C@H]3[C@H]12
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}}
|Section2={{Chembox Properties
| C=15 | H=24
| Density = 0.939 g/mL
| MeltingPt =
| BoilingPtC = 124
| BoilingPt_notes = (15 mmHg)
}}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 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. It is of economic significance because it is strongly attracting to an agricultural pest, the Mediterranean fruit fly Ceratitis capitata.^[3]

References

1. ^{{cite journal | author= V.H. Kapadia |year=1963 |journal=Tetrahedron Letters | volume=28 | page=1933 | doi= 10.1016/S0040-4039(01)90945-1 | title= Structure of mustakone and copaene | issue= 28|last2=Nagasampagi |first2=B.A. |last3=Naik |first3=V.G. |last4=Dev |first4=Sukh |display-authors=etal}}
2. ^{{cite journal | author=L. Westfelt |year=1967| journal=Acta Chemica Scandinavica|volume =21 |page=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.}}
3. ^{{Cite journal|author = R. Nishida |year=2000 |journal=Journal of Chemical Ecology |volume=26|page=87|doi = 10.1023/A:1005489411397|last2=Shelly |first2=Todd E. |last3=Whittier |first3=Timothy S. |last4=Kaneshiro |first4=Kenneth Y. |display-authors=etal}}