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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

(4S)-1-methyl-4-prop-1-en-2-ylcyclohexene

Metabolic Pathways

Structure

IUPAC Name

(4S)-1-methyl-4-prop-1-en-2-ylcyclohexene

PubChem CID

439250

Synonymous Names

Formula

C10H16

Molecular Weight

136.23

Chemical Class

Terpenoid, Aliphatic, Olefin, Prenol

Reference Link

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.
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. 1990. Further observations on rhythmic emission of fragrance in flowers. Planta. 180:194–7.
Buttery, R. G., Kamm, J. A., and Ling, L. C. 1982. Volatile components of alfalfa flowers and pods. J Agric Food Chem. 30:739–742.
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.
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.
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., Groth, I., and Anders Nilsson, L. 1992. Floral fragrance disparity between three taxa of lady’s slipper Cypripedium calceolus (orchidaceae). Phytochemistry. 31:2315–2319.
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.
Hamilton-Kemp, T. R., Loughrin, J. H., and Andersen, R. A. 1990. Identification of some volatile compounds from strawberry flowers. Phytochemistry. 29:2847–2848.
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
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.
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.
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.
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
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.
Ahmed, Q., Aljuboory, A. B., and Alsabte, A. 2022. The Response of Bitter Orange Citrus Aurantium Trees to the Infestation of Oriental Yellow Scale Aonidiella Orientalis in Iraq. IOP Conf Ser Earth Environ Sci. 1060:012092.

Plants/Microbial Species and Abiotic/Biotic Stimuli

Plant/Microbial Species	Abiotic/Biotic Stimuli
Lycopersicon esculentum (Tomato)	Heat - High Temperature
Solanum tuberosum (Potato)	Virus - Potato leaf roll virus (PLRV)
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Alnus glutinosa (Black Alder)	Insect - Cabera pusaria
Allium sativum (Garlic)	Fungi - Sclerotium cepivorum
Phaseolus vulgaris (Bean)	Fungi - Colletotrichum lindemuthianum
Citrus medica (Citron)	None
Cypripedium calceolus (Lady's slipper orchid)	None
Medicago sativa (Alfalfa)	None
Picea abies (Norway spruce)	None
Nicotiana suaveolens	None
Nicotiana alata (Jasmine tobacco)	None
Fragaria x ananassa Duch. (Strawberry)	None
Dendrobium chrysotoxum	None
Oryza sativa (Rice)	None
Citrus sinensis (Sweet orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Pyrus communis (Pear)	None
Malus domestica (Apple)	None
Glycine max (Soybean)	None
Citrus reticulata (Mandarin orange)	None
Citrus paradisi (Grapefruit)	None
Citrus limon (Lemon)	None
Citrus aurantifolia (Lime)	None
Citrus bergamia (Bergamot orange)	None
Citrus junos (Yuzu)	None
Citrus grandis (Pummelo)	Insect - Diaphorina citri - Asian Citrus Psyllid
Citrus aurantium (Bitter orange)	Insect - Aonidiella orientalis - Yellow Scale
Citrus grandis (Pummelo)	Bacteria - Candidatus Liberibacter - asiaticus
Citrus sinensis (Sweet orange)	Insect - Diaphorina citri - Asian Citrus Psyllid
Citrus sinensis (Sweet orange)	Bacteria - Candidatus Liberibacter - asiaticus

Confirmed/Hypothesized Functions

Pollinator attractant