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Plant-Associated Volatile Organic Compound (VOC) Database (PVD)

A database supporting research and application of VOCs produced by plants and plant-associated microbes

(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene

Metabolic Pathways

Structure

IUPAC Name

(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene

PubChem CID

5281520

Synonymous Names

Formula

C15H24

Molecular Weight

204.35

Chemical Class

Sesquiterpenoid, Aliphatic, Olefin, Prenol

Reference Link

De Moraes, C. M., Mescher, M. C., and Tumlinson, J. H. 2001. Caterpillar-induced nocturnal plant volatiles repel conspecific females. Nature. 410:577–80.
Rodriguez-Saona, C. R., Rodriguez-Saona, L. E., and Frost, C. J. 2009. Herbivore-induced volatiles in the perennial shrub, Vaccinium corymbosum, and their role in inter-branch signaling. J Chem Ecol. 35:163–75.
Bergstrom, G., Birgersson, G., Groth, I., and Anders Nilsson, L. 1992. Floral fragrance disparity between three taxa of lady’s slipper Cypripedium calceolus (orchidaceae). Phytochemistry. 31:2315–2319.
Mauck, K. E., De Moraes, C. M., and Mescher, M. C. 2010. Deceptive chemical signals induced by a plant virus attract insect vectors to inferior hosts. Proceedings of the National Academy of Sciences. 107:3600–3605.
Eigenbrode, S. D., Ding, H., Shiel, P., and Berger, P. H. 2002. Volatiles from potato plants infected with potato leafroll virus attract and arrest the virus vector, Myzus persicae (Homoptera: Aphididae). Proc Biol Sci. 269:455–60.
Copolovici, L., Kännaste, A., Pazouki, L., and Niinemets, U. 2012. Emissions of green leaf volatiles and terpenoids from Solanum lycopersicum are quantitatively related to the severity of cold and heat shock treatments. J Plant Physiol. 169:664–72.
Pare, P. W., and Tumlinson, J. H. 1997. De Novo Biosynthesis of Volatiles Induced by Insect Herbivory in Cotton Plants. Plant Physiol. 114:1161–1167.
Loughrin, J. H., Hamilton-Kemp, T. R., Andersen, R. A., and Hildebrand, D. F. 1990. Headspace compounds from flowers of Nicotiana tabacum and related species. J Agric Food Chem. 38:455–460.
Ángeles López, Y. I., Martínez-Gallardo, N. A., Ramírez-Romero, R., López, M. G., Sánchez-Hernández, C., and Délano-Frier, J. P. 2012. Cross-kingdom effects of plant-plant signaling via volatile organic compounds emitted by tomato (Solanum lycopersicum)
Michereff, M. F. F., Laumann, R. A., Borges, M., Michereff-Filho, M., Diniz, I. R., Neto, A. L. F., et al. 2011. Volatiles mediating a plant-herbivore-natural enemy interaction in resistant and susceptible soybean cultivars. J Chem Ecol. 37:273–85.
González-Mas, M. C., Rambla, J. L., López-Gresa, M. P., Blázquez, M. A., and Granell, A. 2019. Volatile Compounds in Citrus Essential Oils: A Comprehensive Review. Front Plant Sci. 10:12.
Strapasson, P., Pinto-Zevallos, D. M., Da Silva Gomes, S. M., and Zarbin, P. H. G. 2016. Volatile Organic Compounds Induced by Herbivory of the Soybean Looper Chrysodeixis includens in Transgenic Glyphosate-Resistant Soybean and the Behavioral Effect on
Hijaz, F., El-Shesheny, I., and Killiny, N. 2013. Herbivory by the insect diaphorina citri induces greater change in citrus plant volatile profile than does infection by the bacterium, Candidatus Liberibacter asiaticus. Plant Signal Behav. 8:doi: 10.4161
Fereres, A., Peñaflor, M. F. G. V, Favaro, C. F., Azevedo, K. E. X., Landi, C. H., Maluta, N. K. P., et al. 2016. Tomato Infection by Whitefly-Transmitted Circulative and Non-Circulative Viruses Induce Contrasting Changes in Plant Volatiles and Vector Be
Jones, S. E., and Killiny, N. 2021. Influence of Rootstock on the Leaf Volatile Organic Compounds of Citrus Scion Is More Pronounced after the Infestation with Diaphorina citri. Plants (Basel). 10.
da Cruz, M. A., Plotto, A., Ferrarezi, R. S., Leite Junior, R. P., and Bai, J. 2023. Effect of Huanglongbing on the Volatile Organic Compound Profile of Fruit Juice and Peel Oil in “Ray Ruby” Grapefruit. Foods. 12.

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Lycopersicon esculentum (Tomato)	Heat - High Temperature
Cucurbita pepo (Squash)	Virus - Cucumber mosais virus (CMV)
Solanum tuberosum (Potato)	Virus - Potato leaf roll virus (PLRV)
Vaccinium corymbosum (Blueberry)	Insect - Lymantina dispar
Nicotiana tabacum (Tobacco)	Insect - Heliothios virescens
Nicotiana tabacum (Tobacco)	Insect - Heliothis zea
Nicotiana tabacum (Tobacco)	Insect - Manduca sexta
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Cypripedium calceolus (Lady's slipper orchid)	None
Nicotiana sylvestris	None
Lycopersicon esculentum (Tomato)	Insect - Trialeurodes vaporariorum - Whitefly
Glycine max (Soybean)	Insect - Chrysodeixis includens - Soybean Looper
Citrus grandis (Pummelo)	None
Citrus aurantifolia (Lime)	None
Citrus limon (Lemon)	None
Citrus aurantium (Bitter orange)	None
Citrus bergamia (Bergamot orange)	None
Citrus junos (Yuzu)	None
Citrus medica (Citron)	None
Citrus sinensis (Sweet orange)	Insect - Diaphorina citri - Asian Citrus Psyllid
Citrus reticulata (Mandarin orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Citrus paradisi (Grapefruit)	Insect - Diaphorina citri - Asian Citrus Psyllid
Lycopersicon esculentum (Tomato)	Virus - Tomato chlorosis virus (ToCV)
Citrus paradisi (Grapefruit)	Bacteria - Candidatus Liberibacter - asiaticus

Confirmed/Hypothesized Functions