Eucalyptol
| Eucalyptol | |
|---|---|
 | |
| IUPAC name | 1,3,3-trimethyl- 2-oxabicyclo[2,2,2]octane |
| Identifiers | |
| CAS number | [470-82-6] |
| SMILES |
CC1(C2CCC(O1)(CC2)C)C |
| Properties | |
| Molecular formula | C10H18O |
| Molar mass | 154.249 g/mol |
| Density | 0.9225 g/cm³ |
| Melting point |
1.5 °C ( 274.66 K) |
| Boiling point |
176 - 177 °C (449 - 450 K) |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and 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, Cloez, identified and ascribed the name eucalyptol to the dominant portion of Eucalyptus globulus oil.[1]"Eucalyptus oil", a generic collective name for oils from the eucalyptus genus, should not be confused with the isolate eucalyptol.
Composition
Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus oil,[2] hence the common name of the compound. It is also found in bay leaves, 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 high doses.[citation needed]
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
Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics. It is also an ingredient in many brands of mouthwash and cough suppressant. Eucalyptol has been demonstrated to be capable of reducing inflammation and pain.[citation needed] It has also been found to be able to kill leukaemic cells in vitro.[3]
Cineol was shown to be an effective treatment for nonpurulent rhinosinusitis in a placebo controlled trial.[4] 76 patients per treatment group were assigned to cineole or placebo. The dosage of the active ingredient was two 100 mg capsules of cineole three times daily. Symptom scores were significantly reduced in the cineole group. The mean values for the symptoms-sum-scores in the cineole group were 6.9 ± 2.9 after 4 days and 3.0 ± 2.8 after 7 days, and in the placebo group, 12.2 ± 2.5 after 4 days and 9.2 ± 3.0 after 7 days. 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.
In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is added to improve the flavor.
It 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.[5]
References
- Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, p6 ISBN 0-909605-69-6
- Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, p23 ISBN 0-909605-69-6
- Oncology Reports 9: 757-760, 2002 PMID 12066204
- 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. PMID 15064633.
- Schiestl, F.P. & Roubik, D.W. (2004) Odor Compound Detection in Male Euglossine Bees. Journal of Chemical Ecology 29: 253-257. Abstract
External links
- Eucalyptus at Botanical.com
- Oleum Eucalypti, B.P. Oil of Eucalyptus at Henriette's Herbal
- Safety data for eucalyptol from Oxford University Chemistry Department
Source: adapted by the editor from Wikipedia, the free encyclopedia; from the article "Eucalyptol". Image Credit.
