Eucalyptol
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Names | |||
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IUPAC name
1,3,3-trimethyl- 2-oxabicyclo[2,2,2]octane
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Other names
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
1,8-Cineole 1,8-Epoxy-p-menthane | |||
Identifiers | |||
3D model (JSmol)
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ChEMBL | |||
ChemSpider | |||
DrugBank | |||
ECHA InfoCard | 100.006.757 | ||
KEGG | |||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C10H18O | |||
Molar mass | 154.249 g/mol | ||
Density | 0.9225 g/cm3 | ||
Melting point | 1.5 °C (274.6 K) | ||
Boiling point | 176–177 °C (449–450 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Eucalyptol is a natural organic compound which 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, limonene oxide, 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] Eucalyptus oil, the generic collective name for oils from the Eucalyptus genus, should not be confused with the chemical compound eucalyptol.
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, wormwood, rosemary, sage 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 camphor-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 halogen 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. It is claimed that it is added to improve the flavor.
Medicinal
Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant.
Insecticide and repellent
Eucalyptol is used as an insecticide and insect repellent.[4][5]
Conversely, eucalyptol is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.[6]
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
This section needs more reliable medical references for verification or relies too heavily on primary sources. (September 2012) |
- 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.[7][8]
- In a 2004 study it was found to inhibit cytokine production in cultured human lymphocytes and monocytes.[9]
- 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.[10]
- A 2000 study found eucalyptol to reduce inflammation and pain when applied topically.[11]
- 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.[12]
List of plants that contain the chemical
- Cinnamomum camphora, Camphor laurel (50%)[13]
- Eucalyptus cneorifolia [citation needed]
- Eucalyptus dives, [citation needed]
- Eucalyptus dumosa [citation needed]
- Eucalyptus globulus[14]
- Eucalyptus goniocalyx [citation needed]
- Eucalyptus horistes [citation needed]
- Eucalyptus kochii [citation needed]
- Eucalyptus leucoxylon [citation needed]
- Eucalyptus oleosa [citation needed]
- Eucalyptus polybractea [citation needed]
- Eucalyptus radiata [citation needed]
- Eucalyptus staigeriana[15]
- Eucalyptus sideroxylon [citation needed]
- Eucalyptus smithii [citation needed]
- Eucalyptus tereticornis [citation needed]
- Eucalyptus viridis [citation needed]
- Helichrysum gymnocephalum [16]
- Turnera diffusa[17]
- Zingiber officinale [citation needed]
- Kaempferia galanga, Galangal, (5.7%)[18]
- Laurus nobilis, Bay Laurel, (45%) [citation needed]
- Melaleuca alternifolia, Tea-tree, (0–15%) [citation needed]
- Umbellularia californica, Pepperwood (22.0%)[19]
Compendial status
N.B. Listed as "cineole" in some pharmacopoeia.
See also
Notes and references
- ^ 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.
- ^ a b "Material Safety Data Sheet - Cineole MSDS". ScienceLab. Retrieved 9/27/2012.
{{cite web}}
: Check date values in:|accessdate=
(help) - ^ Harborne, J. B.; Baxter, H. Chemical Dictionary of Economic Plants. ISBN 0-471-49226-4.
{{cite book}}
: CS1 maint: multiple names: authors list (link) - ^ Klocke, J. A.; Darlington, M. V.; Balandrin, M. F. (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.
{{cite journal}}
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ignored (help)CS1 maint: multiple names: authors list (link) - ^ Sfara, V.; Zerba, E. N.; Alzogaray, R. A. (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.
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ignored (help)CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ Juergens, U. R.; Dethlefsen, U.; Steinkamp, G.; Gillissen, A.; Repges, R.; Vetter, H. (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.
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ignored (help)CS1 maint: multiple names: authors list (link) - ^ 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.
- ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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. PMID 12066204.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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.
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1002/(SICI)1099-1026(199703)12:2.3C63::AID-FFJ614.3E3.0.CO;2-Z, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1002/(SICI)1099-1026(199703)12:2.3C63::AID-FFJ614.3E3.0.CO;2-Z
instead. - ^ Balch, P. A. (2002). Prescription for Nutritional Healing: the A to Z Guide to Supplements. Penguin. p. 233. ISBN 978-1-58333-143-9.
- ^ 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.
- ^ 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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 5 July 2009.
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(help) - ^ Therapeutic Goods Administration. "Chemical Substances" (pdf). Retrieved 5 July 2009.
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(help) [dead link]
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.
External links
- "Eucalyptus". Botanical.com.
- "Oleum Eucalypti, B.P. Oil of Eucalyptus". Henriette's Herbal.
- "MSDS - Safety data for eucalyptol". Oxford University Chemistry Department. [dead link]