Potency and safety analysis of hemp-derived delta-9 products: The hemp vs. cannabis demarcation problem

IUPAC name
Other names
1,8-epoxy-p-menthane, 1,8-oxido-p-menthane
3D model (JSmol)
105109 5239941
ECHA InfoCard 100.006.757 Edit this at Wikidata
EC Number
  • 207-431-5
  • InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 checkY
  • InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
  • O2C1(CCC(CC1)C2(C)C)C
Molar mass 154.249 g/mol
Density 0.9225 g/cm3
Melting point 2.9 °C (37.2 °F; 276.0 K)
Boiling point 176–177 °C (349–351 °F; 449–450 K)
−116.3×10−6 cm3/mol
R05CA13 (WHO)
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
H226, H304, H315, H317, H319, H411
P210, P233, P240, P241, P242, P243, P261, P264, P272, P273, P280, P301+P310, P302+P352, P303+P361+P353, P305+P351+P338, P321, P331, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Eucalyptol (also called cineole) is a monoterpenoid colorless liquid, and a bicyclic ether.[1] It has a fresh camphor-like odor and a spicy, cooling taste.[1] It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil.[2][3] Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.[4]

In 1870, F. S. Cloez identified and ascribed the name "eucalyptol" to the dominant portion of Eucalyptus globulus oil.[2]


Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.[1] 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.[1][5] In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes.[6] It is claimed to be added to improve the flavor.[1]

Eucalyptol is an ingredient in commercial mouthwashes,[1] and has been used in traditional medicine as a cough suppressant.[7]


Eucalyptol exhibits insecticidal and insect repellent properties.[8][9]

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.[10] 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.[11]


Eucalyptol has a toxicity (LD50) of 2.48 grams per kg (rat).[1] Ingestion in significant quantities is likely to cause headache and gastric distress, such as nausea and vomiting.[1] 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.[1]


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.[12][13][14] 

Plants containing eucalyptol

See also


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  2. ^ a b Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. p. 6. doi:10.1002/ffj.2730070209. ISBN 0-909605-69-6.
  3. ^ "GCMS – Gas Chromatography Mass Spectrometry Analysis" (PDF). New Direction Aromatics. Archived (PDF) from the original on 28 October 2020. Retrieved 7 December 2022.
  4. ^ Eggersdorfer, Manfred (2000). "Terpenes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a26_205. ISBN 978-3527306732.
  5. ^ Harborne, J. B.; Baxter, H. (30 August 2001). Chemical Dictionary of Economic Plants. John Wiley & Sons. ISBN 0-471-49226-4.
  6. ^ "Cigarette Ingredients – Chemicals in Cigarettes". New York State Department of Health. Retrieved 28 July 2014.
  7. ^ "Tea tree oil". Drugs.com. 17 June 2019. Retrieved 31 July 2019.
  8. ^ Klocke, J. A.; Darlington, M. V.; Balandrin, M. F. (December 1987). "8-Cineole (Eucalyptol), a Mosquito Feeding and Ovipositional Repellent from Volatile Oil of Hemizonia fitchii (Asteraceae)". Journal of Chemical Ecology. 13 (12): 2131–41. doi:10.1007/BF01012562. PMID 24301652. S2CID 23271137.
  9. ^ Sfara, V.; Zerba, E. N.; Alzogaray, R. A. (May 2009). "Fumigant Insecticidal Activity and Repellent Effect of Five Essential Oils and Seven Monoterpenes on First-Instar Nymphs of Rhodnius prolixus". Journal of Medical Entomology. 46 (3): 511–515. doi:10.1603/033.046.0315. hdl:11336/82775. PMID 19496421. S2CID 23452066.
  10. ^ Schiestl, F. P.; Roubik, D. W. (2004). "Odor Compound Detection in Male Euglossine Bees". Journal of Chemical Ecology. 29 (1): 253–257. doi:10.1023/A:1021932131526. hdl:20.500.11850/57276. PMID 12647866. S2CID 2845587.
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  13. ^ Wise, Mitchell L.; Savage, Thomas J.; Katahira, Eva; Croteau, Rodney (12 June 1998). "Monoterpene Synthases From Common Sage (Salvia Officinalis): cDNA Isolation, Characterization, and Functional Expression of (+)-Aabinene Synthase, 1,8-Cineole Synthase, and (+)-Bo..." Journal of Biological Chemistry. 273 (24): 14891–14899. doi:10.1074/jbc.273.24.14891. ISSN 0021-9258.
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