Eucalyptol

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Eucalyptol
File:Eucalyptol.png
File:Eucalyptol3D-3.png
File:Eucalyptol3D-4.png
IUPAC name
1,3,3-trimethyl- 2-oxabicyclo[2,2,2]octane
Other names
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
1,8-Cineole
1,8-Epoxy-p-menthane
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 470-82-6 YesY
ChemSpider 2656
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style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula 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)

 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

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

File:Eucalyptol suppository.jpg
Eucalyptol suppository, for the treatment of some respiratory ailments

Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant. It controls airway mucus hypersecretion and asthma via anti-inflammatory cytokine inhibition.[4][5] Eucalyptol is an effective treatment for nonpurulent rhinosinusitis.[6] Research showed that 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.

Eucalyptol reduces inflammation and pain when applied topically.[7] It kills leukaemia cells in vitro.[8]


Insecticide and repellent

Eucalyptol is used as an insecticide and insect repellent.[9][10]

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.[11]

List of plants that contain the chemical

Toxicology

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

Compendial status

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

Notes and references

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Further reading

  • Boland, D.J.; Brophy, J.J.; House, A.P.N. (1991). Eucalyptus Leaf Oils. ISBN 0-909605-69-6. 

See also

External links

es:Aceite de eucalipto fr:Eucalyptol id:Eukaliptol it:Eucaliptolo hu:Cineol ja:シネオール pl:Eukaliptol

ru:Цинеол
  1. ↑ 1.0 1.1 Boland, Brophy & House 1991, p. 6
  2. ↑ 2.0 2.1 Material Safety Data Sheet - Cineole MSDS, Bio Org
  3. ↑ Harborne, J.B., Baxter, H. Chemical Dictionary of Economic Plants. ISBN 0-471-49226-4. 
  4. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  5. ↑ 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): 281–7. doi:10.1016/j.pupt.2004.06.002. 
  6. ↑ Kehrl W, Sonnemann U, Dethlefsen U (2004). "Therapy for acute nonpurulent rhinosinusitis with cineole: results of a double-blind, randomized, placebo-controlled trial". Laryngoscope. 114 (4): 738–42. doi:10.1097/00005537-200404000-00027. PMID 15064633. 
  7. ↑ Santos FA, Rao VSN (2000). "Antiinflammatory and antinociceptive effects of 1,8-cineole a terpenoid oxide present in many plant essential oils". Phytotherapy research. 14 (4): 240–4. doi:10.1002/1099-1573(200006)14:4<240::AID-PTR573>3.0.CO;2-X. 
  8. ↑ 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 a in human stomach cancer cell line". Oncol. Rep. 9 (4): 757–60. PMID 12066204. 
  9. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  10. ↑ Lua error in package.lua at line 80: module 'Module:Citation/CS1/Suggestions' not found.
  11. ↑ Schiestl FP, Roubik DW (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology. 29 (1): 253–7. doi:10.1023/A:1021932131526. PMID 12647866. 
  12. ↑ Stubbs, B.J., Brushett, D. (2001). "Leaf oil of Cinnamomum camphora (L.) Nees and Eberm. From Eastern Australia". Journal of Essential Oil Research. 13: 51–4. 
  13. ↑ Maciel M.V.; et al. (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. 
  14. ↑ Gilles, M.; Zhao, J.; An, Min; Agboola, Samson (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. 
  15. ↑ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Compositon of the essential oil of rhizomes of Kaempferia Galanga L.". Flavour and Fragrance Journal. 7 (5): 263–6. doi:10.1002/ffj.2730070506. 
  16. ↑ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 5 July 2009. 
  17. ↑ Therapeutic Goods Administration. "Chemical Substances" (PDF). Retrieved 5 July 2009. 
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