Copaene

Copaene: (-)-α-Copaene (top)
(-)-β-Copaene (bottom)

IUPAC name

(1R,2S,6S,7S,8S)-8-isopropyl-1,3-
dimethyltricyclo[4.4.0.0^2,7]dec-3-ene

Identifiers

CAS number 3856-25-5^Y

ChemSpider 10231594^Y

Jmol-3D images Image 1

SMILES

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

InChI

InChI=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^Y
Key: VLXDPFLIRFYIME-BTFPBAQTSA-N^Y
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
Key: VLXDPFLIRFYIME-BTFPBAQTBX

Properties

Molecular formula C₁₅H₂₄

Molar mass 204.36 g/mol

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 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]

References

^ V.H. Kapadia et al. (1963). "Structure of mustakone and copaene". Tetrahedron Letters 28 (28): 1933. doi:10.1016/S0040-4039(01)90945-1.

^ L. Westfelt; Westfelt, Lars; Sky, K.; Nilsson, Åke; Theorell, H.; Blinc, R.; Paušak, S.; Ehrenberg, L. et al. (1967). "Beta-Copaene and beta-Ylangene, Minor Sesquiterpenes of the Wood of Pinus silvestris L. And of Swedish Sulphate Turpentine". Acta Chemica Scandinavica 21: 152. doi:10.3891/acta.chem.scand.21-0152.

^ R. Nishida et al. (2000). Journal of Chemical Ecology 26: 87. doi:10.1023/A:1005489411397.

Categories:
Alkenes
Sesquiterpenes

(-)-α-Copaene (top) (-)-β-Copaene (bottom)


IUPAC name (1R,2S,6S,7S,8S)-8-isopropyl-1,3- dimethyltricyclo[4.4.0.0^2,7]dec-3-ene
Identifiers
CAS number	3856-25-5^Y
ChemSpider	10231594^Y
Jmol-3D images	Image 1
SMILES CC(C)[C@@H]1CC[C@@]3(C)[C@@H]2C(/C)=C\C[C@H]3[C@H]12
InChI InChI=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^Y Key: VLXDPFLIRFYIME-BTFPBAQTSA-N^Y 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 Key: VLXDPFLIRFYIME-BTFPBAQTBX
Properties
Molecular formula	C₁₅H₂₄
Molar mass	204.36 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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copaene — co·pa·ene … English syllables
copaene — kōˈpāˌēn, ˈ ̷ ̷ ̷ ̷ˌ ̷ ̷ noun ( s) Etymology: copaiba + ene chemistry : an oily tricyclic sesquiterpene C15H24 occurring in certain essential oils (as oil of supa) … Useful english dictionary
Ravensara aromatica — Scientific classification Kingdom: Plantae (unranked): Angiosperms (unranked): Magnoliids … Wikipedia
Mangosteen — Taxobox name = Mangosteen image width = 250px image caption = Mangosteen fruit regnum = Plantae divisio = Magnoliophyta classis = Magnoliopsida ordo = Malpighiales familia = Clusiaceae genus = Garcinia species = G. mangostana binomial = Garcinia… … Wikipedia
Cubeb — In West Africa, cubeb is usually the related West African Pepper (Piper guineense). Cubeb Scientific classification Kingdom … Wikipedia
Sesquiterpene — Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications… … Wikipedia
Eriocephalus africanus — Taxobox name = Cape snow bush regnum = Plantae divisio = Magnoliophyta classis = Magnoliopsida ordo = Asterales familia = Asteraceae genus = Eriocephalus species = Eriocephalus africanus binomial = Eriocephalus africanus Also known as the Cape… … Wikipedia
Copaifera langsdorffii — Diesel tree Copaifera langsdorfii in a park in São Paulo Brazil. Scientific classification Kingdom … Wikipedia
Copaifera — officinalis Scientific classification Kingdom: Plantae … Wikipedia
Baume de la Mecque — Myrrhe 100 g de résine de myrrhe L arbre à myrrhe … Wikipédia en Français

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Copaene

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