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1,8-Cineole

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1,8-Cineole

Eucalyptol
Identifiers
CAS number 470-82-6 YesY
PubChem 2758
ChemSpider 2656 YesY
UNII RV6J6604TK YesY
DrugBank DB03852
KEGG D04115 YesY
Jmol-3D images Image 1
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 (verify) (what is: YesY/N?)
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 that 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, 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, cannabis sativa, 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, as well as an inactive ingredient in body powder.

Insecticide and repellent

Eucalyptol is used as an insecticide and insect repellent.[4][5]

In contrast, eucalyptol is one of many compounds that are attractive to males of various species of orchid bees, which 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

  • 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

Compendial status

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

See also

Notes and references

Further reading

External links


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