α-Copaene

  • CAT Number: R033304
  • CAS Number: 3856-25-5
  • Molecular Formula: C₁₅H₂₄
  • Molecular Weight: 204.35
  • Purity: ≥95%
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Copaene, or more precisely, α-copaene(CAS: 3856-25-5), 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 langsdorffii, from which the compound was first isolated in 1914. Its structure, including the chirality, was determined in 1963. The double-bond isomer with an exocyclic-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.

Catalog Number R033304
CAS Number 3856-25-5
Synonyms

Copaene; 1,3-dimethyl-8-propan-2-yltricyclo[4.4.0.02,7]dec-3-ene; .alpha.-ylangene.

Molecular Formula

C₁₅H₂₄

Purity 95%
Storage -20°C
IUPAC Name 1,3-dimethyl-8-propan-2-yltricyclo[4.4.0.02,7]dec-3-ene
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
InChIKey VLXDPFLIRFYIME-UHFFFAOYSA-N
SMILES CC1=CCC2C3C1C2(CCC3C(C)C)C
Reference

[1]. J Agric Food Chem. 2014 Dec 10;62(49):11976-9. doi: 10.1021/jf504821a. Epub 2014 Dec 1.<br />
Role of &alpha;-copaene in the susceptibility of olive fruits to Bactrocera oleae (Rossi).<br />
de Alfonso I(1), Vacas S, Primo J.<br />
Author information: (1)Ecologı́a y Protecci&oacute;n Agrı́cola, S.L., Apartado de Correos no. 50, 46240 Carlet, Spain.<br />
The influence of &alpha;-copaene as a fruit volatile in the susceptibility of Olea europaea L. to the olive fruit fly Bactrocera oleae (Rossi) has been investigated. By studies on the relative area of volatile components from different cultivars, a positive correlation was found between the abundance of &alpha;-copaene in the samples and the corresponding degree of fruit infestation. SPME-GC-MS analysis of volatiles from uninfested fruits of O. europaea L. cv. Serrana were performed over two years to determine the variation of &alpha;-copaene throughout the different phenological stages. The results suggested that this sesquiterpene has a significant effect on cultivar susceptibility and may act as an oviposition promoter. Further analysis by chiral GC showed that olive fruits release both &alpha;-copaene enantiomers. Bioassays on each enantiomer revealed that fruits with increased amounts of (+)-&alpha;-copaene favor oviposition of B. oleae females, whereas the increase of (-)-&alpha;-copaene affords no statistically significant differences in host preference.<br />
DOI: 10.1021/jf504821a PMID: 25408316 [Indexed for MEDLINE]<br />
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[2]. J Econ Entomol. 2016 Dec;109(6):2428-2435. doi: 10.1093/jee/tow214. Epub 2016 Oct 23.<br />
Efficacy of &alpha;-Copaene, Cubeb, and Eucalyptol Lures for Detection of Redbay Ambrosia Beetle (Coleoptera: Curculionidae: Scolytinae).<br />
Kendra PE(1), Montgomery WS(2), Schnell EQ(2), Deyrup MA(3), Epsky ND(2).<br />
Author information: (1)USDA-ARS, Subtropical Horticulture Research Station, 13601 Old Cutler Rd., Miami, FL 33158 ([email protected]; [email protected]; [email protected]; [email protected]) [email protected]. (2)USDA-ARS, Subtropical Horticulture Research Station, 13601 Old Cutler Rd., Miami, FL 33158 ([email protected]; [email protected]; [email protected]; [email protected]). (3)Archbold Biological Station, P.O. Box 2057, Lake Placid, FL 33862 ([email protected]).<br />
Redbay ambrosia beetle, Xyleborus glabratus Eichhoff, is a wood-boring pest that has now invaded nine states in the southeastern United States. The beetle&#39;s dominant fungal symbiont (Raffaelea lauricola) is phytopathogenic, inducing laurel wilt in trees within the family Lauraceae. Members of the genus Persea are particularly susceptible to the lethal disease, including native redbay (P. borbonia) and swampbay (P. palustris), as well as commercial avocado (P. americana). Cubeb oil lures are the current standard for detection of X. glabratus, but recently eucalyptol and a 50% &alpha;-copaene oil have been identified as additional attractants. This study used a combination of binary-choice bioassays, field cage release-and-recapture assays, and a 12-wk field trial to compare efficacy of eucalyptol and copaene lures relative to commercial cubeb lures. In addition, GC-MS was used to quantify emissions from lures field-aged for 12 wk. In laboratory bioassays, copaene lures were more attractive than eucalyptol lures. In field cage assays, copaene lures recaptured a higher percentage of released beetles than cubeb lures. In the field test, cubeb lures captured fewer beetles than copaene lures, and lowest captures were obtained with eucalyptol lures. Combining eucalyptol with either copaene or cubeb lures did not increase captures over those lures deployed alone. Both copaene and cubeb lures were effective in attracting X. glabratus for 12 wk, but field life of eucalyptol lures was only 4 wk, consistent with the quantification of lure emissions. Results suggest that the 50% &alpha;-copaene lure provides the best pest detection currently available for X. glabratus.<br />
Published by Oxford University Press on behalf of Entomological Society of America 2016. This work is written by US Government employees and is in the public domain in the US.<br />
DOI: 10.1093/jee/tow214 PMID: 27986939 [Indexed for MEDLINE]<br />
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[3]. Phytochemistry. 2011 Dec;72(18):2288-93. doi: 10.1016/j.phytochem.2011.08.023. Epub 2011 Sep 10.<br />
Utilisation of the MVA pathway to produce elevated levels of the sesquiterpene &alpha;-copaene in potato tubers.<br />
Morris WL(1), Ducreux LJ, Shepherd T, Lewinsohn E, Davidovich-Rikanati R, Sitrit Y, Taylor MA.<br />
Author information: (1)Plant Products and Food Quality, The James Hutton Institute, Invergowrie, Dundee, UK. [email protected]<br />
Potato flavour is a complex trait resulting from the presence of a combination of volatile and non-volatile compounds. The aim of this work was to investigate the effect of specifically altering the volatile content of tubers and assess its impact on flavour. Tuber-specific over-expression of a potato &alpha;-copaene synthase gene resulted in enhanced levels (up to 15-fold higher than controls) of the sesquiterpene &alpha;-copaene. A positive correlation (R(2)=0.8) between transgene expression level and &alpha;-copaene abundance was observed. No significant changes in the levels of volatiles other than &alpha;-copaene were detected. Non-volatile flavour compounds (sugars, glycoalkaloids, major umami amino acids and 5&#39;-ribonucleotides) were also determined. Relationships between flavour compounds and sensory evaluation data were investigated. Evaluators could not detect any aroma differences in the transgenic samples compared with controls and no significant differences in taste attributes were found. Thus although successful engineering of potato tubers to accumulate high levels of the flavour volatile &alpha;-copaene was achieved, sensory analysis suggests that &alpha;-copaene is not a major component of potato flavour.<br />
DOI: 10.1016/j.phytochem.2011.08.023 PMID: 21911234 [Indexed for MEDLINE]<br />
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[4]. J Chem Ecol. 1994 Oct;20(10):2595-609. doi: 10.1007/BF02036194.<br />
Male lures for mediterranean fruitfly (Ceratitis capitata wied.): Structural analogs of &alpha;-copaene.<br />
Flath RA(1), Cunningham RT, Mon TR, John JO.<br />
Author information: (1)USDA-ARS, Western Regional Research Center, 800 Buchanan Street, 94710, Albany, California.<br />
Nine sesquiterpenes structurally related to the potent male Mediterranean fruit fly lure (+)-&alpha;-copaene were tested in a series of field bioassays to determine their male medfly attractiveness relative to one another and to (+)-&alpha;-copaene itself. This study was carried out to determine the relative importance of the various substructure components of the (+)-&alpha;-copaene molecule in eliciting an attractive response in the male fly. Tests indicated that any deviation from the three-dimensional structure of (+)-&alpha;-copaene leads to major losses in male fly attractancy. The tested analogs fell into two groups, based on their levels of attraction: (+)-&alpha;-ylangene, (+)-&beta;-copaene, (+)-&beta;-ylangene, and (-)-&alpha;-copaene were found to be somewhat attractive, although much less so than (+)-&alpha;-copaene, while (+)-cyclosativene, (+)-cyclocopacamphene, (+)-longicyclene, (+)-longipinene, and (-)-trans-&alpha;-bergamotene were not attractive.<br />
DOI: 10.1007/BF02036194 PMID: 24241834<br />
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[5]. PLoS One. 2017 Jun 13;12(6):e0179416. doi: 10.1371/journal.pone.0179416. eCollection 2017.<br />
&alpha;-Copaene is an attractant, synergistic with quercivorol, for improved detection of Euwallacea nr. fornicatus (Coleoptera: Curculionidae: Scolytinae).<br />
Kendra PE(1), Owens D(1), Montgomery WS(1), Narvaez TI(1), Bauchan GR(2), Schnell EQ(1), Tabanca N(1), Carrillo D(3).<br />
Author information: (1)United States Department of Agriculture, Agricultural Research Service, Subtropical Horticulture Research Station, Miami, FL, United States of America. (2)United States Department of Agriculture, Agricultural Research Service, Beltsville Area Research Center, Electron and Confocal Microscopy Unit, Beltsville, MD, United States of America. (3)University of Florida, Tropical Research and Education Center, Homestead, FL, United States of America.<br />
The tea shot-hole borer, Euwallacea fornicatus Eichhoff, is an ambrosia beetle endemic to Asia and a pest of commercial tea, Camellia sinensis (L.) Kuntze. Recently, a complex of species morphologically similar to E. fornicatus has been recognized, which includes new pests established in Israel and the USA, both in California and Florida. Collectively termed E. nr. fornicatus, these cryptic species carry symbiotic Fusarium spp. fungi, some of which cause dieback disease in susceptible hosts, which include avocado, Persea americana Miller. Due to the threat to this economically important crop, research was initiated to evaluate efficacy of kairomone-based lures for detection of the beetle in Florida (termed the Florida tea shot hole borer, FL-TSHB). A series of field tests were conducted in 2016 in commercial avocado groves known to have FL-TSHB at various population levels. All tests evaluated lures containing quercivorol (p-menth-2-en-1-ol) and &alpha;-copaene, presented separately and in combination; and one test evaluated effect of trap type on beetle captures. In addition, electroantennography (EAG) was used to quantify female olfactory responses to lure emissions. This study identified (-)-&alpha;-copaene as a new attractant for FL-TSHB, equivalent in efficacy to quercivorol (the standard lure for Euwallacea detection in the USA); however, the combination of lures captured significantly more FL-TSHB than either lure alone. This combination resulted in synergistic attraction at two field sites and additive attraction at a third site. Sticky panel traps captured more FL-TSHB than comparably-baited Lindgren funnel traps. Females engaged in host-seeking flight from 11:00 to 16:00 hr (EST), with peak numbers observed between 12:00 and 13:00 hr. EAG analyses confirmed olfactory chemoreception of both kairomones, with a higher response elicited with the combination of volatiles. Results indicate that detection of pest E. nr. fornicatus in Florida can be improved by using a two-component lure consisting of p-menth-2-en-1-ol and (-)-&alpha;-copaene.<br />
DOI: 10.1371/journal.pone.0179416 PMCID: PMC5469513 PMID: 28609448 [Indexed for MEDLINE]

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