PVD

3,7-dimethylocta-1,6-dien-3-ol

Metabolic Pathways

Structure

IUPAC Name

3,7-dimethylocta-1,6-dien-3-ol

PubChem CID

6549

Synonymous Names

Formula

C10H18O

Molecular Weight

154.25

Chemical Class

Terpenoid, Alcohol, Aliphatic, 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.
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
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
Altenburger, R., and Matile, P. 1988. Circadian rhythmicity of fragrance emission in flowers of Hoya carnosa R. Br. Planta. 174:248–52.
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
Altenburger, R., and Matile, P. 1990. Further observations on rhythmic emission of fragrance in flowers. Planta. 180:194–7.
37:18–28. 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.
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.
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.
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.
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.
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.
Horvat, R. J., Chapman, G. W., Robertson, J. A., Meredith, F. I., Scorza, R., Callahan, A. M., et al. 1990. Comparison of the volatile compounds from several commercial peach cultivars. J Agric Food Chem. 38:234–237.
Aubert, C., Baumann, S., and Arguel, H. 2005. Optimization of the analysis of flavor volatile compounds by liquid-liquid microextraction (LLME). Application to the aroma analysis of melons, peaches, grapes, strawberries, and tomatoes. J Agric Food Chem.
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
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
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.
Ulrich, D., Kecke, S., and Olbricht, K. 2018. What Do We Know about the Chemistry of Strawberry Aroma? J Agric Food Chem. 66:3291–3301.
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
Lou, Y.-G., Ma, B., and Cheng, J.-A. 2005. Attraction of the parasitoid Anagrus nilaparvatae to rice volatiles induced by the rice brown planthopper Nilaparvata lugens. J Chem Ecol. 31:2357–72.
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.
Pingault, L., Varsani, S., Palmer, N., Ray, S., Williams, W. P., Luthe, D. S., et al. 2021. Transcriptomic and volatile signatures associated with maize defense against corn leaf aphid. BMC Plant Biol. 21:138.

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
Cucurbita pepo (Squash)	Virus - Cucumber mosais virus (CMV)
Zea mays	Insect - Spodoptera littoralis
Nicotiana tabacum (Tobacco)	Bacteria - Pseudomonas syringae
Gossypium kirsutum (Cotton)	Insect - Spodoptera exigua Hubner
Phaseolus vulgaris (Bean)	Fungi - Colletotrichum lindemuthianum
Hoya carnosa (Porcelain flower)	None
Stephanotis floribunda Brongs (Madagascar jasmine)	None
Citrus medica (Citron)	None
Cypripedium calceolus (Lady's slipper orchid)	None
Nicotiana tomentosiformis	None
Dendrobium chrysotoxum	None
Dendrobium harveyanum	None
Prunus persica (Peach)	None
Malus domestica (Apple)	Insect - Epiphyas postvittana - Light Brown Apple Moth
Fragaria x ananassa Duch. (Strawberry)	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
Oryza sativa (Rice)	Insect - Nilaparvata lugens - Rice Brown Leafhopper
Citrus reticulata (Mandarin orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Glycine max (Soybean)	Insect - Chrysodeixis includens - Soybean Looper
Citrus sinensis (Sweet orange)	Insect - Diaphorina citri - Asian Citrus Psyllid
Citrus sinensis (Sweet orange)	Insect - Ceratitis capitata Wiedemann - Mediterranean Fruit Fly
Zea mays	Insect - Rhopalosiphum maidis - Corn Leaf Aphid

Confirmed/Hypothesized Functions

Circadian rhythm

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

3,7-dimethylocta-1,6-dien-3-ol