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Eucalyptol

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Eucalyptol
Names
IUPAC name
1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octane
Other names
1,8-Cineole
1,8-Epoxy-p-menthane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.757 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 checkY
    Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
    Key: WEEGYLXZBRQIMU-UHFFFAOYAY
  • O2C1(CCC(CC1)C2(C)C)C
Properties
C10H18O
Molar mass 154.249 g/mol
Density 0.9225 g/cm3
Melting point 1.5 °C (34.7 °F; 274.6 K)
Boiling point 176 to 177 °C (349 to 351 °F; 449 to 450 K)
Pharmacology
R05CA13 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Eucalyptol is a natural organic compound that is a colorless liquid. It is a cyclic ether and a monoterpenoid.

Eucalyptol is also known by a variety of synonyms: 1,8-cineol, 1,8-cineole, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane, cineol, cineole.

In 1870, F. S. Cloez identified and ascribed the name eucalyptol to the dominant portion of Eucalyptus globulus oil.[1]

Composition

Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus oil,[1] hence the common name of the compound. It is also found in camphor laurel, bay leaves, tea tree, mugwort, sweet basil[citation needed], wormwood, rosemary, common sage, Cannabis sativa and other aromatic plant foliage. Eucalyptol with a purity from 99.6 to 99.8 percent can be obtained in large quantities by fractional distillation of eucalyptus oil.

Although it can be used internally as a flavoring and medicine ingredient at very low doses, typical of many essential oils (volatile oils), eucalyptol is toxic if ingested at higher than normal doses.[2]

Properties

Eucalyptol has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with ether, ethanol, and chloroform. The boiling point is 176 °C and the flash point is 49 °C. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts are useful for purification.

Uses

Flavoring and fragrance

Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products and beverages.[3] In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes.[4] It is claimed that it is added to improve the flavor.

Medicinal

Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant, as well as an inactive ingredient in body powder.

Insecticide and repellent

Eucalyptol is used as an insecticide and insect repellent.[5][6]

In contrast, eucalyptol is one of many compounds that are attractive to males of various species of orchid bees, which gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[7] One such study with Euglossa imperialis, a non-social orchid bee species, has shown that the presence of cineole (also eucalyptol), elevates territorial behavior and specifically attracts the male bees. It was even observed that these males would periodically leave their territories to forage for chemicals such as cineole, thought to be important for attracting and mating with females, to synthesize pheromones.[8]

Toxicology

In higher-than-normal doses, eucalyptol is hazardous via ingestion, skin contact, or inhalation. It can have acute health effects on behavior, respiratory tract, and nervous system. The acute oral LD50 is 2480 mg/kg (rat). It is classified as a reproductive toxin for females and a suspect reproductive toxin for males.[2]

Scientific study

  • In a 2003 study, eucalyptol was found to control airway mucus hypersecretion and asthma; after, in a previous study, the authors found eucalyptol to suppress arachidonic acid metabolism and cytokine production in human monocytes.[9][10]
  • In a 2004 study, it was found to inhibit cytokine production in cultured human lymphocytes and monocytes.[11]
  • In a 2004 study, eucalyptol was found to be an effective treatment for nonpurulent rhinosinusitis. Treated subjects experienced less headache on bending, frontal headache, sensitivity of pressure points of trigeminal nerve, impairment of general condition, nasal obstruction, and rhinological secretion. Side effects from treatment were minimal.[12]
  • A 2000 study found eucalyptol to reduce inflammation and pain when applied topically.[13]
  • In a 2002 study, it was found to kill leukaemia cells of two cultured human leukemia cell lines, but not cells of a human stomach cancer cell line in vitro.[14]

List of plants that contain the chemical

[24] [25] [26] [27]

Compendial status

N.B. Listed as "cineole" in some pharmacopoeia.

Sulfonation

See also

References

  1. ^ a b Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. p. 6. ISBN 0-909605-69-6.
  2. ^ a b "Material Safety Data Sheet - Cineole MSDS". ScienceLab. Retrieved 27 September 2012.
  3. ^ Harborne, J. B.; Baxter, H. Chemical Dictionary of Economic Plants. ISBN 0-471-49226-4.
  4. ^ "Cigarette Ingredients - Chemicals in Cigarettes". New York State Department of Health. Retrieved 28 July 2014.
  5. ^ Klocke, J. A.; Darlington, M. V.; Balandrin, M. F. (December 1987). "8-Cineole (Eucalyptol), a Mosquito Feeding and Ovipositional Repellent from Volatile Oil of Hemizonia fitchii (Asteraceae)". Journal of Chemical Ecology. 13 (12): 2131. doi:10.1007/BF01012562.
  6. ^ Sfara, V.; Zerba, E. N.; Alzogaray, R. A. (May 2009). "Fumigant Insecticidal Activity and Repellent Effect of Five Essential Oils and Seven Monoterpenes on First-Instar Nymphs of Rhodnius prolixus". Journal of Medical Entomology. 46 (3): 511–515. doi:10.1603/033.046.0315. PMID 19496421.
  7. ^ Schiestl, F. P.; Roubik, D. W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology. 29 (1): 253–257. doi:10.1023/A:1021932131526. PMID 12647866.
  8. ^ Schemske, Douglas W., and Russell Lande. "Fragrance collection and territorial display by male orchid bees." Animal Behaviour 32.3 (1984): 935-937.
  9. ^ Juergens, U. R.; Dethlefsen, U.; Steinkamp, G.; Gillissen, A.; Repges, R.; Vetter, H. (March 2003). "Anti-Inflammatory Activity of 1.8-Cineol (Eucalyptol) in Bronchial Asthma: A Double-Blind Placebo-Controlled Trial" (pdf). Respiratory Medicine. 97 (3): 250–256. doi:10.1053/rmed.2003.1432. PMID 12645832.
  10. ^ Juergens, U. R.; Stöber, M.; Vetter, H. (1998). "Inhibition of Cytokine Production and Arachidonic Acid Metabolism by Eucalyptol (1.8-Cineole) in Human Blood Monocytes in vitro". European Journal of Medical Research. 3 (11): 508–510. PMID 9810029.
  11. ^ Juergens, U.; Engelen, T.; Racké, K.; Stöber, M.; Gillissen, A.; Vetter, H. (2004). "Inhibitory Activity of 1,8-Cineol (Eucalyptol) on Cytokine Production in Cultured Human Lymphocytes and Monocytes". Pulmonary Pharmacology & Therapeutics. 17 (5): 281–287. doi:10.1016/j.pupt.2004.06.002. PMID 15477123.
  12. ^ Kehrl, W.; Sonnemann, U.; Dethlefsen, U. (2004). "Therapy for Acute Nonpurulent Rhinosinusitis with Cineole: Results of a Double-Blind, Randomized, Placebo-Controlled Trial". The Laryngoscope. 114 (4): 738–742. doi:10.1097/00005537-200404000-00027. PMID 15064633.
  13. ^ Santos, F. A.; Rao, V. S. (2000). "Antiinflammatory and Antinociceptive Effects of 1,8-Cineole, a Terpenoid Oxide Present in many Plant Essential Oils". Phytotherapy Research. 14 (4): 240–244. doi:10.1002/1099-1573(200006)14:4<240::AID-PTR573>3.0.CO;2-X. PMID 10861965.
  14. ^ Moteki, H.; Hibasami, H.; Yamada, Y.; Katsuzaki, H.; Imai, K.; Komiya, T. (2002). "Specific Induction of Apoptosis by 1,8-Cineole in two Human Leukemia Cell Lines, but not in a Human Stomach Cancer Cell Line". Oncology Reports. 9 (4): 757–760. doi:10.3892/or.9.4.757. PMID 12066204.
  15. ^ "Cannabis and cannabis extracts: greater than the sum of their parts?". Journal of Cannabis Therapeutics. 1 (3–4): 103–132. 2001. doi:10.1300/J175v01n03_08. Retrieved 20 September 2013. {{cite journal}}: Unknown parameter |authors= ignored (help)
  16. ^ Stubbs, B. J.; Brushett, D. (2001). "Leaf oil of Cinnamomum camphora (L.) Nees and Eberm. From Eastern Australia". Journal of Essential Oil Research. 13 (1): 51–54. doi:10.1080/10412905.2001.9699604.
  17. ^ Maciel, M. V.; Morais, S. M.; Bevilaqua, C. M.; Silva, R. A.; Barros, R. S.; Sousa, R. N.; Sousa, L. C.; Brito, E. S.; Souza-Neto M. A. (2010). "Chemical composition of Eucalyptus spp. essential oils and their insecticidal effects on Lutzomyia longipalpis". Veterinary Parasitology. 167 (1): 1–7. doi:10.1016/j.vetpar.2009.09.053. PMID 19896276.
  18. ^ Gilles, M.; Zhao, J.; An, M.; Agboola, S. (2010). "Chemical Composition and Antimicrobial Properties of Essential Oils of three Australian Eucalyptus Species". Food Chemistry. 119 (2): 731–737. doi:10.1016/j.foodchem.2009.07.021.
  19. ^ Möllenbeck, S.; König, T.; Schreier, P.; Schwab, W.; Rajaonarivony, J.; Ranarivelo, L. (1997). "Chemical Composition and Analyses of Enantiomers of Essential Oils from Madagascar". Flavour and Fragrance Journal. 12 (2): 63. doi:10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z.
  20. ^ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the Essential Oil of Rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
  21. ^ "In-vitro inhibition of human erythrocyte acetylcholinesterase by salvia lavandulaefolia essential oil and constituent terpenes". J Pharm Pharmacol. 52 (7): 895–902. 2000. doi:10.1211/0022357001774598. PMID 10933142. {{cite journal}}: Unknown parameter |authors= ignored (help)
  22. ^ Balch, P. A. (2002). Prescription for Nutritional Healing: the A to Z Guide to Supplements. Penguin. p. 233. ISBN 978-1-58333-143-9.
  23. ^ Kelsey, R. G.; McCuistion, O.; Karchesy, J. (2007). "Bark and Leaf Essential Oil of Umbellularia californica, California Bay Laurel, from Oregon". Natural Product Communications. 2 (7): 779–780.
  24. ^ Ali, S., Sotheeswaran, S., Tuiwawa, M. and Smith, R. (2002). Comparison of the Composition of the Essential Oils of Alpinia and Hedychium Species—Essential Oils of Fijian Plants, Part 1. Journal of Essential Oil Research, vol.14, no.6, p.409-411.
  25. ^ Joy, B., Rajan, A. and Abraham, E. (2007). Antimicrobial Activity and Chemical Composition of Essential Oil from Hedychium coronarium. Phytotherapy research, vol. 21, p. 439–443
  26. ^ Martins, M., Caravante, A., Appezzato-Da-Glória, B., Soares, M., Moreira, R. and Santos, L. (2010). Anatomical characterization and phytochemistry of leaves and rhizomes of Hedychium coronarium J. König (Zingiberaceae), Rev. bras. plantas med., vol. 12, no.2, p.179-187.
  27. ^ Santos, S.B., pedralli, G., meyer, S.T. (2005). Aspectos da fenologia e ecologia de Hedychium coronarium (Zingiberaceae) na estação ecológica do Tripuí, Ouro Preto-MG. Planta daninha, v.23, n.2, p.175- 180
  28. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009. {{cite web}}: Unknown parameter |deadurl= ignored (|url-status= suggested) (help)
  29. ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). tga.gov.au. Archived from the original (PDF) on 2 July 2009. Retrieved 5 July 2009.
  30. ^ U.S. patent 3,397,212 eidem DE 1296646 

Further reading

  • Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. ISBN 0-909605-69-6.

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