PVD

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

Metabolic Pathways

Structure

IUPAC Name

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene

PubChem CID

6654

Synonymous Names

Formula

C10H16

Molecular Weight

136.23

Chemical Class

Terpenoid, Aliphatic, Olefin, Prenol

Reference Link

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.
Paris, C. I., Llusia, J., and Peñuelas, J. 2010. Changes in monoterpene emission rates of Quercus ilex infested by aphids tended by native or invasive Lasius ant species. J Chem Ecol. 36:689–98s
Copolovici, L., Kännaste, A., Remmel, T., Vislap, V., and Niinemets, Ü. 2011. Volatile Emissions from Alnus glutionosa Induced by Herbivory are Quantitatively Related to the Extent of Damage. J Chem Ecol. 37:18–28.
Pontin, M., Bottini, R., Burba, J. L., and Piccoli, P. 2015. Allium sativum produces terpenes with fungistatic properties in response to infection with Sclerotium cepivorum. Phytochemistry. 115:152–160.
Altenburger, R., and Matile, P. 1988. Circadian rhythmicity of fragrance emission in flowers of Hoya carnosa R. Br. Planta. 174:248–52.
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.
Altenburger, R., and Matile, P. 1990. Further observations on rhythmic emission of fragrance in flowers. Planta. 180:194–7.
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.
Borg-Karlson, A.-K., Eidmann, H. H., Lindström, M., Norin, T., and Wiersma, N. 1985. Odoriferous compounds from the flowers of the conifers Picea abies, Pinus sylvestris and Larix sibirica. Phytochemistry. 24:455–456.
Robustelli Della Cuna, F. S., Calevo, J., Bazzicalupo, M., Sottani, C., Grignani, E., and Preda, S. 2021. Chemical Composition of Essential Oil from Flowers of Five Fragrant Dendrobium (Orchidaceae). Plants (Basel). 10.
Chen, P., Dai, C., Liu, H., and Hou, M. 2022. Identification of Key Headspace Volatile Compounds Signaling Preference for Rice over Corn in Adult Females of the Rice Leaf Folder Cnaphalocrocis medinalis. J Agric Food Chem. 70:9826–9833.
Cuevas, F. J., Moreno-Rojas, J. M., and Ruiz-Moreno, M. J. 2017. Assessing a traceability technique in fresh oranges (Citrus sinensis L. Osbeck) with an HS-SPME-GC-MS method. Towards a volatile characterisation of organic oranges. Food Chem. 221:1930–193
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.
Najar-Rodriguez, A., Orschel, B., and Dorn, S. 2013. Season-long volatile emissions from peach and pear trees in situ, overlapping profiles, and olfactory attraction of an oligophagous fruit moth in the laboratory. J Chem Ecol. 39:418–29.
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)
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.
Constantino, N., Oh, Y., Şennik, E., Andersen, B., Warden, M., Oralkan, Ö., et al. 2021. Soybean Cyst Nematodes Influence Aboveground Plant Volatile Signals Prior to Symptom Development. Front Plant Sci. 12:749014.
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
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
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.
Cao, S., Sun, J., Yuan, X., Deng, W., Zhong, B., and Chun, J. 2020. Characterization of Volatile Organic Compounds of Healthy and Huanglongbing-Infected Navel Orange and Pomelo Leaves by HS-GC-IMS. Molecules. 25.

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Lycopersicon esculentum (Tomato)	Heat - High Temperature
Vaccinium corymbosum (Blueberry)	Insect - Lymantina dispar
Quercus ilex (Holm oak)	Insect - Aphidoidea
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Alnus glutinosa (Black Alder)	Insect - Cabera pusaria
Allium sativum (Garlic)	Fungi - Sclerotium cepivorum
Hoya carnosa (Porcelain flower)	None
Citrus medica (Citron)	None
Cypripedium calceolus (Lady's slipper orchid)	None
Picea abies (Norway spruce)	None
Dendrobium chrysotoxum	None
Citrus sinensis (Sweet orange)	Insect - Diaphorina citri - Asian Citrus Psyllid
Prunus persica (Peach)	None
Pyrus communis (Pear)	None
Lycopersicon esculentum (Tomato)	Insect - Trialeurodes vaporariorum - Whitefly
Malus domestica (Apple)	None
Citrus paradisi (Grapefruit)	None
Citrus grandis (Pummelo)	None
Citrus limon (Lemon)	None
Citrus aurantifolia (Lime)	None
Citrus aurantium (Bitter orange)	None
Citrus bergamia (Bergamot orange)	None
Citrus junos (Yuzu)	None
Citrus reticulata (Mandarin orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Glycine max (Soybean)	Nematode - Heterodera glycines - Soybean Nematode Cyst
Lycopersicon esculentum (Tomato)	Virus - Tomato severe rugose virus (ToSRV)
Citrus sinensis (Sweet orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Citrus sinensis (Sweet orange)	Bacteria - Candidatus Liberibacter - asiaticus

Confirmed/Hypothesized Functions

Circadian rhythm
Pollinator attractant

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

2,6,6-trimethylbicyclo[3.1.1]hept-2-ene