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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
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 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]

Uses

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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]

Other

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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

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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

[edit]

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

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See also

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References

[edit]
  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. ^ 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. Bibcode:1987JCEco..13.2131K. 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.
  11. ^ Schemske, Douglas W.; Lande, Russell (1984). "Fragrance collection and territorial display by male orchid bees". Animal Behaviour. 32 (3): 935–937. doi:10.1016/s0003-3472(84)80184-0. S2CID 54411184.
  12. ^ Rinkel, Jan; Rabe, Patrick; zur Horst, Laura; Dickschat, Jeroen S (4 November 2016). "A Detailed View on 1,8-Cineol Biosynthesis by Streptomyces clavuligerus". Beilstein Journal of Organic Chemistry. 12: 2317–2324. doi:10.3762/bjoc.12.225. ISSN 1860-5397. PMC 5238540. PMID 28144299.
  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. PMID 9614092.
  14. ^ Croteau, R.; Alonso, W. R.; Koepp, A. E.; Johnson, M. A. (1 February 1994). "Biosynthesis of Monoterpenes: Partial Purification, Characterization, and Mechanism of Action of 1,8-Cineole Synthase". Archives of Biochemistry and Biophysics. 309 (1): 184–192. doi:10.1006/abbi.1994.1101. ISSN 0003-9861. PMID 8117108.
  15. ^ Sebsebe Demissew (1993). "A description of some essential oil bearing plants in Ethiopia and their indigenous uses". Journal of Essential Oil Research. 5 (5). Taylor & Francis: 465–479. doi:10.1080/10412905.1993.9698266. The chemical composition of … Aframomum corrorima (l, 8-cineole 41.9%) … is also presented.
  16. ^ Crowell, M.M.; et al. (2018). "Dietary partitioning of toxic leaves and fibrous stems differs between sympatric specialist and generalist mammalian herbivores". Journal of Mammalogy. 99 (3): 565–577. doi:10.1093/jmammal/gyy018.
  17. ^ McPartland, J. M.; Russo, E. B. (2001). "Cannabis and cannabis extracts: greater than the sum of their parts?". Journal of Cannabis Therapeutics. 1 (3–4): 103–132. doi:10.1300/J175v01n03_08. Retrieved 20 September 2013.
  18. ^ Stubbs, B. J.; Brushett, D. (2001). "Leaf oil of Cinnamomum camphora (L.) Nees and Eberm. From Eastern Australia". Journal of Essential Oil Research. 13 (1): 51–54. doi:10.1080/10412905.2001.9699604. S2CID 85418932.
  19. ^ Maciel, M. V.; Morais, S. M.; Bevilaqua, C. M.; Silva, R. A.; Barros, R. S.; Sousa, R. N.; Sousa, L. C.; Brito, E. S.; Souza Neto, M. A. (2010). "Chemical composition of Eucalyptus spp. essential oils and their insecticidal effects on Lutzomyia longipalpis" (PDF). Veterinary Parasitology. 167 (1): 1–7. doi:10.1016/j.vetpar.2009.09.053. PMID 19896276. 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. ^ Gilles, M.; Zhao, J.; An, M.; Agboola, S. (2010). "Chemical Composition and Antimicrobial Properties of Essential Oils of three Australian Eucalyptus Species". Food Chemistry. 119 (2): 731–737. doi:10.1016/j.foodchem.2009.07.021.
  23. ^ Ameur, Elaissi; Sarra, Moumni; Yosra, Derbali; Mariem, Kouja; Nabil, Abid; Lynen, Frederic; Larbi, Khouja Mohamed (2021). "Chemical composition of essential oils of eight Tunisian Eucalyptus species and their antibacterial activity against strains responsible for otitis". BMC Complement Med Ther. 21 (1): 209. doi:10.1186/s12906-021-03379-y. PMC 8359536. PMID 34384412.
  24. ^ Ali, S.; Sotheeswaran, S.; Tuiwawa, M.; Smith, R. (2002). "Comparison of the Composition of the Essential Oils of Alpinia and Hedychium Species—Essential Oils of Fijian Plants, Part 1". Journal of Essential Oil Research. 14 (6): 409–411. doi:10.1080/10412905.2002.9699904. S2CID 95463805.
  25. ^ Joy, B.; Rajan, A.; Abraham, E. (2007). "Antimicrobial Activity and Chemical Composition of Essential Oil from Hedychium coronarium". Phytotherapy Research. 21 (5): 439–443. doi:10.1002/ptr.2091. PMID 17245683. S2CID 27756399.
  26. ^ Möllenbeck, S.; König, T.; Schreier, P.; Schwab, W.; Rajaonarivony, J.; Ranarivelo, L. (1997). "Chemical Composition and Analyses of Enantiomers of Essential Oils from Madagascar". Flavour and Fragrance Journal. 12 (2): 63. doi:10.1002/(SICI)1099-1026(199703)12:2<63::AID-FFJ614>3.0.CO;2-Z.
  27. ^ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the Essential Oil of Rhizomes of Kaempferia galanga L.". Flavour and Fragrance Journal. 7 (5): 263–266. doi:10.1002/ffj.2730070506.
  28. ^ Perry, N. S.; Houghton, P. J.; Theobald, A.; Jenner, P.; Perry, E. K. (2000). "In-vitro inhibition of human erythrocyte acetylcholinesterase by Salvia lavandulaefolia essential oil and constituent terpenes". J Pharm Pharmacol. 52 (7): 895–902. doi:10.1211/0022357001774598. PMID 10933142. S2CID 34457692.
  29. ^ Balch, P. A. (2002). Prescription for Nutritional Healing: the A to Z Guide to Supplements. Penguin. p. 233. ISBN 978-1-58333-143-9.
  30. ^ Kelsey, R. G.; McCuistion, O.; Karchesy, J. (2007). "Bark and Leaf Essential Oil of Umbellularia californica, California Bay Laurel, from Oregon". Natural Product Communications. 2 (7): 779–780. doi:10.1177/1934578X0700200715.
  31. ^ Gupta S, Pandotra P, Ram G, Anand R, Gupta AP, Husain K, Bedi YS, Mallavarapu GR (January 2011). "Composition of a monoterpenoid-rich essential oil from the rhizome of Zingiber officinale from north western Himalayas". Natural Product Communications. 6 (1): 93–6. doi:10.1177/1934578X1100600122. PMID 21366054. S2CID 20981360.
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