Eucalyptol

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Eucalyptol
Names
IUPAC name
1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
Other names
1,8-Cineole
1,8-Epoxy-p-menthane
cajeputol
1,8-epoxy-p-menthane, 1,8-oxido-p-menthane
eucalyptole
1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
cineol
cineole.
Identifiers
3D model (
JSmol
)
105109 5239941
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.006.757 Edit this at Wikidata
EC Number
  • 207-431-5
131076
IUPHAR/BPS
KEGG
UNII
  • InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 checkY
    Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N checkY
  • InChI=1/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3
    Key: WEEGYLXZBRQIMU-UHFFFAOYAY
  • O2C1(CCC(CC1)C2(C)C)C
Properties
C10H18O
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
Pharmacology
R05CA13 (WHO)
Hazards
GHS labelling:
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
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

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]

Uses

Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.

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

cough suppressant.[7]

Other

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]

Toxicology

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]

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.[12][13][14] 

Plants containing eucalyptol

See also

References

  1. ^ a b c d e f g h i "Eucalyptol". PubChem, US National Library of Medicine. 22 April 2023. Retrieved 28 April 2023.
  2. ^
    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. ISBN 978-3527306732
    .
  5. 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. S2CID 23271137
    .
  9. S2CID 23452066
    .
  10. S2CID 2845587
    .
  11. S2CID 54411184
    .
  12. PMID 28144299
    .
  13. ISSN 0021-9258
    .
  14. ISSN 0003-9861
    .
  15. doi:10.1080/10412905.1993.9698266
    . The chemical composition of … Aframomum corrorima (l, 8-cineole 41.9%) … is also presented.
  16. doi:10.1093/jmammal/gyy018
    .
  17. doi:10.1300/J175v01n03_08
    . Retrieved 20 September 2013.
  18. S2CID 85418932
    .
  19. S2CID 7665066
    .
  20. ^ Zhang J, An M, Wu H, Stanton R, Lemerle D (2010). "Chemistry and bioactivity of Eucalyptus essential oils" (PDF). Allelopathy Journal. 25 (2): 313–330.
  21. Charles Austin Gardner (1 August 1952). "Trees of Western Australia - salmon gum and scarlet pear gum"
    . Journal of the Department of Agriculture Western Australia Series 3. 1 (4). Department of Primary Industries and Regional Development. Retrieved 23 January 2023.
  22. doi:10.1016/j.foodchem.2009.07.021
    .
  23. PMID 34384412
    .
  24. S2CID 95463805
    .
  25. S2CID 27756399
    .
  26. doi:10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z
    .
  27. doi:10.1002/ffj.2730070506
    .
  28. S2CID 34457692
    .
  29. ISBN 978-1-58333-143-9
    .
  30. doi:10.1177/1934578X0700200715
    .
  31. S2CID 20981360
    .
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