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Eucalyptol

Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

Uses
Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is claimed to be added to improve the flavor. 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. One such study with Euglossa imperialis, a nonsocial orchid bee species, has shown that the presence of cineole (also eucalyptol) elevates territorial behavior and specifically attracts the male bees. It was even observed that these males would periodically leave their territories to forage for chemicals such as cineole, thought to be important for attracting and mating with females, to synthesize pheromones. ==Toxicology==
Toxicology
Eucalyptol has a toxicity (LD50) of 2.48 grams per kg (rat). == Biosynthesis ==
Biosynthesis
Eucalyptol is generated from geranyl pyrophosphate (GPP) which isomerizes to (S)-linalyl diphosphate (LPP). Ionization of the pyrophosphate, catalyzed by cineole synthase, produces eucalyptol. The process involves the intermediacy of alpha-terpinyl cation. ==Plants containing eucalyptol==
Plants containing eucalyptol
Aframomum corrorimaArtemisia tridentataCannabisCinnamomum camphora, camphor laurel (50%) • Eucalyptus globulusEucalyptus largiflorensEucalyptus salmonophloiaEucalyptus staigerianaEucalyptus wandooHedychium coronarium, butterfly lily • Helichrysum gymnocephalumKaempferia galanga, galangal, (5.7%) • S. officinalis subsp. lavandulifolia (syn. S. lavandulifolia), Spanish sage (13%) • Salvia rosmarinus, rosemary • Turnera diffusa, damiana • Umbellularia californica, pepperwood (22.0%) • Zingiber officinale, ginger ==See also==
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