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Chemical Compound Review

Cineolum     4,7,7-trimethyl-8- oxabicyclo[2.2.2]octane

Synonyms: Cajeputol, Eucapur, Soledum, cineole, CINEOL, ...
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Disease relevance of cineole


Psychiatry related information on cineole


High impact information on cineole

  • Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase [7].
  • Simulations further suggested that linalool and 1,8-cineole synthesis rates also decreased with decreasing G(V), possibly as the result of selective inhibition of various monoterpene synthases by stomata [8].
  • 1,8-Cineole, representing 2% of TTO, reduced vascular changes induced by sensory neuropeptides released when the distal portion of a cut sciatic nerve was electrically stimulated [9].
  • Loss of 260-nm-absorbing material occurred after treatment with concentrations equivalent to the MIC, particularly after treatment with 1,8-cineole and alpha-terpineol [10].
  • All of the above compounds except cineole inhibited the growth of viral Ha-ras-transformed rat liver epithelial cells (WB-ras cells) at concentrations of 0.25-2.5 mM [11].

Chemical compound and disease context of cineole


Biological context of cineole

  • Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation [17].
  • The suction pipette technique was used to study simultaneously the odour-induced action potential and receptor current responses in frog olfactory receptor cells, which were exposed to the odour cineole for 1 s by rapidly exchanging the solution bathing their cilia [18].
  • The present study was undertaken to investigate the pharmacokinetics of 1,8-cineol in human subjects during prolonged inhalation [17].
  • METHODS: In experiment 1, we determined pharmacokinetic profiles of alcohol and of an aromatic substance (cineole) in amniotic fluid and maternal blood during late gestation [19].
  • The effects of three terpene enhancers, (+)-limonene, nerolidol and 1,8-cineole, on stratum corneum structure were monitored [20].

Anatomical context of cineole


Associations of cineole with other chemical compounds

  • 1. TRPM8 (CMR1) is a Ca(2+)-permeable channel, which can be activated by low temperatures, menthol, eucalyptol and icilin [26].
  • The monoterpenes 1,8-cineole, thymol, geraniol, menthol and camphor strongly inhibited the root growth of Zea mays L. seedlings [27].
  • The results obtained through gas chromatographic analysis allowed a second experiment in which we explicitly paired peak levels of cineole with peak levels of alcohol in amniotic fluid and blood, by intragastrically administering cineole and ethanol to the dams during gestational days 17 through 20 (paired condition) [19].
  • The oedema response to 20 microl 1,8-cineole was significantly inhibited throughout its time-course in rats pretreated with antihistaminic and antiserotonergic drugs such as diphenhydramine, methysergide and cyproheptadine or with ketotifen, a mast cell stabilizer [22].
  • Furthermore, 1,8-cineole was able to cause rat peritoneal mast cell degranulation (94%) in vitro, in a concentration as low as 0.3 microl/ml, which was almost comparable to that produced by 0.1 microg/ml of compound 48/80 [22].

Gene context of cineole


Analytical, diagnostic and therapeutic context of cineole

  • Control groups were dams given cineole 4 hr before commencement of an acute state of alcohol intoxication (long-delay group) or were only exposed to water administrations (water control group) [19].
  • Previous work has demonstrated the capability of near-infrared (NIR) spectroscopy to determine the cineole content (not less than 70% w/w) of eucalyptus oil with an accuracy comparable with that of the British Pharmacopoeia (BP) assay method [30].
  • Gas chromatography/mass spectrometry identified terpinen-4-ol (42 %), a-terpineol (3 %) and 1,8-cineole (2%, respectively, of tea tree oil) as the water soluble components of tea tree oil [31].
  • METHODS: Cytokine production was determined following 20 h of incubation cells with 1,8-cineol simultaneously with the stimuli in culture supernatants by enzyme immunoassay [28].
  • Pretreatment of anesthetized rats with bilateral vagotomy significantly reduced the bradycardic responses to 1,8-cineole (10 mg/kg) without affecting hypotension [32].


  1. Cytochrome P450(cin) (CYP176A), isolation, expression, and characterization. Hawkes, D.B., Adams, G.W., Burlingame, A.L., Ortiz de Montellano, P.R., De Voss, J.J. J. Biol. Chem. (2002) [Pubmed]
  2. Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis. Steeghs, M., Bais, H.P., de Gouw, J., Goldan, P., Kuster, W., Northway, M., Fall, R., Vivanco, J.M. Plant Physiol. (2004) [Pubmed]
  3. Mutagenicity testing (+/-)-camphor, 1,8-cineole, citral, citronellal, (-)-menthol and terpineol with the Salmonella/microsome assay. Gomes-Carneiro, M.R., Felzenszwalb, I., Paumgartten, F.J. Mutat. Res. (1998) [Pubmed]
  4. Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line. Moteki, H., Hibasami, H., Yamada, Y., Katsuzaki, H., Imai, K., Komiya, T. Oncol. Rep. (2002) [Pubmed]
  5. Blood levels of 1,8-cineole and locomotor activity of mice after inhalation and oral administration of rosemary oil. Kovar, K.A., Gropper, B., Friess, D., Ammon, H.P. Planta Med. (1987) [Pubmed]
  6. Feeding Behavior of Lambs in Relation to Kinetics of 1,8-cineole Dosed Intravenously or into the Rumen. Dziba, L.E., Hall, J.O., Provenza, F.D. J. Chem. Ecol. (2006) [Pubmed]
  7. Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase. Wise, M.L., Savage, T.J., Katahira, E., Croteau, R. J. Biol. Chem. (1998) [Pubmed]
  8. Stomatal constraints may affect emission of oxygenated monoterpenoids from the foliage of Pinus pinea. Niinemets, U., Reichstein, M., Staudt, M., Seufert, G., Tenhunen, J.D. Plant Physiol. (2002) [Pubmed]
  9. Regulation of wheal and flare by tea tree oil: complementary human and rodent studies. Khalil, Z., Pearce, A.L., Satkunanathan, N., Storer, E., Finlay-Jones, J.J., Hart, P.H. J. Invest. Dermatol. (2004) [Pubmed]
  10. Mechanism of action of Melaleuca alternifolia (tea tree) oil on Staphylococcus aureus determined by time-kill, lysis, leakage, and salt tolerance assays and electron microscopy. Carson, C.F., Mee, B.J., Riley, T.V. Antimicrob. Agents Chemother. (2002) [Pubmed]
  11. Growth inhibition of rat liver epithelial tumor cells by monoterpenes does not involve Ras plasma membrane association. Ruch, R.J., Sigler, K. Carcinogenesis (1994) [Pubmed]
  12. Characterization of a root-specific Arabidopsis terpene synthase responsible for the formation of the volatile monoterpene 1,8-cineole. Chen, F., Ro, D.K., Petri, J., Gershenzon, J., Bohlmann, J., Pichersky, E., Tholl, D. Plant Physiol. (2004) [Pubmed]
  13. Susceptibility of pseudomonads to Melaleuca alternifolia (tea tree) oil and components. Papadopoulos, C.J., Carson, C.F., Hammer, K.A., Riley, T.V. J. Antimicrob. Chemother. (2006) [Pubmed]
  14. 1,8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis. Santos, F.A., Silva, R.M., Campos, A.R., De Araújo, R.P., Lima Júnior, R.C., Rao, V.S. Food Chem. Toxicol. (2004) [Pubmed]
  15. Antimicrobial effects of tea-tree oil and its major components on Staphylococcus aureus, Staph. epidermidis and Propionibacterium acnes. Raman, A., Weir, U., Bloomfield, S.F. Lett. Appl. Microbiol. (1995) [Pubmed]
  16. Antimicrobial activity of essential oil and methanol extracts of Achillea sintenisii Hub. Mor. (Asteraceae). Sökmen, A., Vardar-Unlü, G., Polissiou, M., Daferera, D., Sökmen, M., Dönmez, E. Phytotherapy research : PTR. (2003) [Pubmed]
  17. Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation. Jäger, W., Nasel, B., Nasel, C., Binder, R., Stimpfl, T., Vycudilik, W., Buchbauer, G. Chem. Senses (1996) [Pubmed]
  18. Adaptation-induced changes in sensitivity in frog olfactory receptor cells. Reisert, J., Matthews, H.R. Chem. Senses (2000) [Pubmed]
  19. Fetal associative learning mediated through maternal alcohol intoxication. Abate, P., Pepino, M.Y., Domínguez, H.D., Spear, N.E., Molina, J.C. Alcohol. Clin. Exp. Res. (2000) [Pubmed]
  20. Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment. Cornwell, P.A., Barry, B.W., Stoddart, C.P., Bouwstra, J.A. J. Pharm. Pharmacol. (1994) [Pubmed]
  21. Oxidation of 1,8-cineole, the monoterpene cyclic ether originated from eucalyptus polybractea, by cytochrome P450 3A enzymes in rat and human liver microsomes. Miyazawa, M., Shindo, M., Shimada, T. Drug Metab. Dispos. (2001) [Pubmed]
  22. Mast cell involvement in the rat paw oedema response to 1,8-cineole, the main constituent of eucalyptus and rosemary oils. Santos, F.A., Rao, V.S. Eur. J. Pharmacol. (1997) [Pubmed]
  23. Whole-cell recordings and photolysis of caged compounds in olfactory sensory neurons isolated from the mouse. Lagostena, L., Menini, A. Chem. Senses (2003) [Pubmed]
  24. A functional map in rat olfactory epithelium. Scott, J.W., Brierley, T. Chem. Senses (1999) [Pubmed]
  25. Relaxant effects of the essential oil of Eucalyptus tereticornis and its main constituent 1,8-cineole on guinea-pig tracheal smooth muscle. Coelho-de-Souza, L.N., Leal-Cardoso, J.H., de Abreu Matos, F.J., Lahlou, S., Magalhães, P.J. Planta Med. (2005) [Pubmed]
  26. Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. Behrendt, H.J., Germann, T., Gillen, C., Hatt, H., Jostock, R. Br. J. Pharmacol. (2004) [Pubmed]
  27. Effect of monoterpenes on lipid oxidation in maize. Zunino, M.P., Zygadlo, J.A. Planta (2004) [Pubmed]
  28. Inhibitory activity of 1,8-cineol (eucalyptol) on cytokine production in cultured human lymphocytes and monocytes. Juergens, U.R., Engelen, T., Racké, K., Stöber, M., Gillissen, A., Vetter, H. Pulmonary pharmacology & therapeutics. (2004) [Pubmed]
  29. Screening of chemical composition and antifungal and antioxidant activities of the essential oils from three Turkish artemisia species. Kordali, S., Cakir, A., Mavi, A., Kilic, H., Yildirim, A. J. Agric. Food Chem. (2005) [Pubmed]
  30. The quantification of citral in lemongrass and lemon oils by near-infrared spectroscopy. Wilson, N.D., Ivanova, M.S., Watt, R.A., Moffat, A.C. J. Pharm. Pharmacol. (2002) [Pubmed]
  31. Terpinen-4-ol, the main component of the essential oil of Melaleuca alternifolia (tea tree oil), suppresses inflammatory mediator production by activated human monocytes. Hart, P.H., Brand, C., Carson, C.F., Riley, T.V., Prager, R.H., Finlay-Jones, J.J. Inflamm. Res. (2000) [Pubmed]
  32. Cardiovascular effects of 1,8-cineole, a terpenoid oxide present in many plant essential oils, in normotensive rats. Lahlou, S., Figueiredo, A.F., Magalhães, P.J., Leal-Cardoso, J.H. Can. J. Physiol. Pharmacol. (2002) [Pubmed]
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