Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclic ether.[ It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil.]
In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.
Uses
Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.[ Cineole-based eucalyptus oil is used as a flavoring at low levels (0.002%) in various products, including baked goods, confectionery, meat products, and beverages.][
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Eucalyptol is an ingredient in commercial ,[ and has been used in traditional medicine as a cough suppressant.]
Other
Eucalyptol exhibits insecticide and insect repellent properties.
In contrast, eucalyptol is one of many compounds that are attractive to males of various species of , which gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study.
Toxicology
Eucalyptol has a toxicity (LD50) of 2.48 grams per kg (rat).[ Ingestion in significant quantities is likely to cause headache and gastric distress, such as nausea and vomiting.][ Because of its low viscosity, it may directly enter the lungs if swallowed, or if subsequently vomited. Once in the lungs, it is difficult to remove and can cause delirium, convulsions, severe injury or death.][
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Biosynthesis
Eucalyptol is generated from geranyl pyrophosphate (GPP) which isomerizes to linalool (LPP). Ionization of the pyrophosphate, catalyzed by cineole synthase, produces eucalyptol. The process involves the intermediacy of alpha-terpinyl cation.
Plants containing eucalyptol
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Aframomum corrorima
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Artemisia tridentata
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Cannabis
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Cinnamomum camphora, camphor laurel (50%)
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Eucalyptus globulus
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Eucalyptus largiflorens
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''Eucalyptus salmonophloia
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Eucalyptus staigeriana
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Eucalyptus wandoo
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Hedychium coronarium, butterfly lily
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Helichrysum gymnocephalum
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Kaempferia galanga, galangal, (5.7%)
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S. officinalis subsp. lavandulifolia (syn. S. lavandulifolia), Spanish sage (13%)
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''Rosemary, rosemary
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Turnera diffusa, damiana
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Umbellularia californica, pepperwood (22.0%)
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Zingiber officinale, ginger
See also
