Eucalyptol

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Eucalyptol

Chemical name	1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
Chemical formula	C₁₀H₁₈O
Molecular mass	154.249 g/mol
CAS number	[470-82-6]
Density	0.9225 g/cm³
Melting point	1.5 °C ( 274.66 K)
Boiling point	176 - 177 °C (449 - 450 K)
SMILES	CC1(C2CCC(O1)(CC2)C)C
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Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpene.

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.

1 Composition
2 Properties
3 Uses
4 External links

[edit] Composition

Eucalyptol comprises up to 90 percent of the essential oil of some species of eucalyptus (e.g.Eucalyptus polybractea),^{[citation needed]} 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.

Health Warning: In common with all volatile oils (essential oils), eucalyptus oil is toxic if ingested internally.

[edit] 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.

[edit] Uses

Eucalyptol suppository, for the treatment of some respiratory ailments

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. It has also been found to be able to kill leukaemic cells[1].

Cineol was shown to be an effective treatment for Nonpurulent sinusitis in a placebo controlled trial. Laryngoscope. 2004 Apr;114(4):738-42. PMID: 15064633 [PubMed - indexed for MEDLINE] 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.