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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

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

Metabolic Pathways

Structure

IUPAC Name

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

PubChem CID

5281516

Synonymous Names

Formula

C15H24

Molecular Weight

204.35

Chemical Class

Alkatetraene, Sesquiterpenoid, Oxane, Aliphatic, Olefin

Reference Link

Huang, J., Cardoza, Y. J., Schmelz, E. A., Raina, R., Engelberth, J., and Tumlinson, J. H. 2003. Differential volatile emissions and salicylic acid levels from tobacco plants in response to different strains of Pseudomonas syringae. Planta. 217:767–75.
De Moraes, C. M., Mescher, M. C., and Tumlinson, J. H. 2001. Caterpillar-induced nocturnal plant volatiles repel conspecific females. Nature. 410:577–80.
Jardine, K. J., Chambers, J. Q., Holm, J., Jardine, A. B., Fontes, C. G., Zorzanelli, R. F., et al. 2015. Green Leaf Volatile Emissions during High Temperature and Drought Stress in a Central Amazon Rainforest. Plants (Basel). 4:678–90.
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.
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.
Degen, T., Dillmann, C., Marion-Poll, F., and Turlings, T. C. J. 2004. High genetic variability of herbivore-induced volatile emission within a broad range of maize inbred lines. Plant Physiol. 135:1928–38.
Quintana-Rodriguez, E., Morales-Vargas, A. T., Molina-Torres, J., Ádame-Alvarez, R. M., Acosta-Gallegos, J. A., and Heil, M. 2015. Plant volatiles cause direct, induced and associational resistance in common bean to the fungal pathogen Colletotrichum lin
Bergstrom, G., Birgersson, G., Grot B h, I., and Anders Nilsson, L. 1992. Floral fragrance disparity between three taxa of lady’s slipper cypripedium calceolus (orchidaceae). Phytochemistry. 31:2315–2319.
Attaran, E., Rostás, M., and Zeier, J. 2008. Pseudomonas syringae elicits emission of the terpenoid (E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraene in Arabidopsis leaves via jasmonate signaling and expression of the terpene synthase TPS4. Mol Plant Micro
Suckling, D. M., Twidle, A. M., Gibb, A. R., Manning, L. M., Mitchell, V. J., Sullivan, T. E. S., et al. 2012. Volatiles from apple trees infested with light brown apple moth larvae attract the parasitoid Dolichogenidia tasmanica. J Agric Food Chem. 60:9
Giacomuzzi, V., Cappellin, L., Khomenko, I., Biasioli, F., Schütz, S., Tasin, M., et al. 2016. Emission of Volatile Compounds from Apple Plants Infested with Pandemis heparana Larvae, Antennal Response of Conspecific Adults, and Preliminary Field Trial.
Vallat, A., Gu, H., and Dorn, S. 2005. How rainfall, relative humidity and temperature influence volatile emissions from apple trees in situ. Phytochemistry. 66:1540–50.
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.
Guo, H., Shi, X., Han, J., Ren, Q., Gao, Z., Zhang, A., et al. 2023. VOCs from fungi-infected apples attract and increase the oviposition of yellow peach moth Conogethes punctiferalis. Pest Manag Sci.
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
Chamberlain, K., Briens, M., Jacobs, J. H., Clark, S. J., and Pickett, J. A. 2012. Use of honey bees (Apis mellifera L.) to detect the presence of Mediterranean fruit fly (Ceratitis capitata Wiedemann) larvae in Valencia oranges. J Sci Food Agric. 92:205
Staudt, M., Jackson, B., El-Aouni, H., Buatois, B., Lacroze, J.-P., Poëssel, J.-L., et al. 2010. Volatile organic compound emissions induced by the aphid Myzus persicae differ among resistant and susceptible peach cultivars and a wild relative. Tree Phys

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Couepia longipendula	Heat - High Temperature
Nicotiana tabacum (Tobacco)	Insect - Heliothios virescens
Nicotiana tabacum (Tobacco)	Insect - Heliothis zea
Nicotiana tabacum (Tobacco)	Insect - Manduca sexta
Vaccinium corymbosum (Blueberry)	Insect - Lymantina dispar
Nicotiana tabacum (Tobacco)	Bacteria - Pseudomonas syringae
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Zea mays	Insect - Spodoptera littoralis
Arabidopsis thaliana (Thale cress, Mouse-ear cress)	Bacteria - Pseudomonas syringae
Phaseolus vulgaris (Bean)	Fungi - Colletotrichum lindemuthianum
Cypripedium calceolus (Lady's slipper orchid)	None
Malus domestica (Apple)	Insect - Epiphyas postvittana - Light Brown Apple Moth
Glycine max (Soybean)	Insect - Euschistus heros - Stink bug
Malus domestica (Apple)	Fungi - Penicillium crustosum
Malus domestica (Apple)	Fungi - Rhizopus oryzae
Malus domestica (Apple)	Fungi - Colletotrichum gloeosporioides
Citrus reticulata (Mandarin orange)	None
Citrus grandis (Pummelo)	None
Citrus paradisi (Grapefruit)	None
Citrus limon (Lemon)	None
Citrus aurantifolia (Lime)	None
Citrus aurantium (Bitter orange)	None
Citrus bergamia (Bergamot orange)	None
Citrus junos (Yuzu)	None
Citrus medica (Citron)	None
Citrus sinensis (Sweet orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Glycine max (Soybean)	Insect - Chrysodeixis includens - Soybean Looper
Prunus persica (Peach)	Insect - Myzus persicae - Green Peach Aphid

Confirmed/Hypothesized Functions