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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, 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.

Additional recommended knowledge

Contents

Composition

Eucalyptol comprises up to 90 percent of the essential oil of some species of eucalyptus (e.g.Eucalyptus polybractea),[1] 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.

In common with many essential oils (volatile oils), eucalyptus oil is toxic if ingested internally.[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.[2]

Cineol was shown to be an effective treatment for nonpurulent rhinosinusitis in a placebo controlled trial.[3] 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.[4]

Eucalyptus Oil can also be used as an effective way of killing dust mites according to the Asthma Foundation of Victoria.[5]

Although there are over 500 species of the Eucalyptus tree worldwide, eucalyptol can be mainly found in Australia as the Australian Gum Tree.

References

  1. ^ Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, p23 ISBN 0-909605-69-6
  2. ^ Oncology Reports 9: 757-760, 2002[1]
  3. ^ 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.
  4. ^ Schiestl, F.P. & Roubik, D.W. (2004) Odor Compound Detection in Male Euglossine Bees. Journal of Chemical Ecology 29: 253-257. Abstract
  5. ^ Asthma Foundation of Victoria
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Eucalyptol". A list of authors is available in Wikipedia.
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