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Eucalyptol

January 01, 1970

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]

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
  • 470-82-6 Y
3D model (JSmol)
  • Interactive image
105109 5239941
ChEBI
  • CHEBI:27961
ChEMBL
  • ChEMBL485259 Y
ChemSpider
  • 2656 Y
DrugBank
  • DB03852 Y
ECHA InfoCard 100.006.757
EC Number
  • 207-431-5
131076
  • 2464
KEGG
  • D04115 Y
  • 2758
UNII
  • RV6J6604TK Y
  • DTXSID4020616
  • InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 Y
    Key: WEEGYLXZBRQIMU-UHFFFAOYSA-N Y
  • 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:
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).

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

Uses edit

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 edit

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 edit

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 edit

See also edit

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. (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.
  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.
  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.
  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.

January 01, 1970
eucalyptol, also, called, cineole, monoterpenoid, colorless, liquid, bicyclic, ether, fresh, camphor, like, odor, spicy, cooling, taste, insoluble, water, miscible, with, organic, solvents, makes, about, eucalyptus, forms, crystalline, adducts, with, hydrohali. 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 Eucalyptol Names IUPAC name 1 3 3 Trimethyl 2 oxabicyclo 2 2 2 octane Other names 1 8 Cineole1 8 Epoxy p menthanecajeputol1 8 epoxy p menthane 1 8 oxido p menthane eucalyptole1 3 3 trimethyl 2 oxabicyclo 2 2 2 octanecineolcineole Identifiers CAS Number 470 82 6 Y 3D model JSmol Interactive image Beilstein Reference 105109 5239941 ChEBI CHEBI 27961 ChEMBL ChEMBL485259 Y ChemSpider 2656 Y DrugBank DB03852 Y ECHA InfoCard 100 006 757 EC Number 207 431 5 Gmelin Reference 131076 IUPHAR BPS 2464 KEGG D04115 Y PubChem CID 2758 UNII RV6J6604TK Y CompTox Dashboard EPA DTXSID4020616 InChI InChI 1S C10H18O c1 9 2 8 4 6 10 3 11 9 7 5 8 h8H 4 7H2 1 3H3 YKey WEEGYLXZBRQIMU UHFFFAOYSA N YInChI 1 C10H18O c1 9 2 8 4 6 10 3 11 9 7 5 8 h8H 4 7H2 1 3H3Key WEEGYLXZBRQIMU UHFFFAOYAY SMILES O2C1 CCC CC1 C2 C C C Properties Chemical formula 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 Magnetic susceptibility x 116 3 10 6 cm3 mol Pharmacology ATC code R05CA13 WHO Hazards GHS labelling Pictograms Signal word Danger Hazard statements H226 H304 H315 H317 H319 H411 Precautionary statements 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 Infobox references In 1870 F S Cloez identified and ascribed the name eucalyptol to the dominant portion of Eucalyptus globulus oil 2 Contents 1 Uses 1 1 Other 2 Toxicology 3 Biosynthesis 4 Plants containing eucalyptol 5 See also 6 ReferencesUses editBecause 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 edit 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 editEucalyptol 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 editEucalyptol 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 nbsp Plants containing eucalyptol editAframomum corrorima 15 Artemisia tridentata 16 Cannabis 17 Cinnamomum camphora camphor laurel 50 18 Eucalyptus globulus 19 Eucalyptus largiflorens 20 Eucalyptus salmonophloia 21 Eucalyptus staigeriana 22 Eucalyptus wandoo 23 Hedychium coronarium butterfly lily 24 25 Helichrysum gymnocephalum 26 Kaempferia galanga galangal 5 7 27 S officinalis subsp lavandulifolia syn S lavandulifolia Spanish sage 13 28 Turnera diffusa damiana 29 Umbellularia californica pepperwood 22 0 30 Zingiber officinale ginger 31 See also editCamphor Citral Eucalyptus oil Lavandula Menthol MouthwashReferences edit a b c d e f g h i Eucalyptol PubChem US National Library of Medicine 22 April 2023 Retrieved 28 April 2023 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 GCMS Gas Chromatography Mass Spectrometry Analysis PDF New Direction Aromatics Archived PDF from the original on 28 October 2020 Retrieved 7 December 2022 Eggersdorfer Manfred 2000 Terpenes Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a26 205 ISBN 978 3527306732 Harborne J B Baxter H 30 August 2001 Chemical Dictionary of Economic Plants John Wiley amp Sons ISBN 0 471 49226 4 Cigarette Ingredients Chemicals in Cigarettes New York State Department of Health Retrieved 28 July 2014 Tea tree oil Drugs com 17 June 2019 Retrieved 31 July 2019 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 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 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 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 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 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 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 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 amp Francis 465 479 doi 10 1080 10412905 1993 9698266 The chemical composition of Aframomum corrorima l 8 cineole 41 9 is also presented 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 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 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 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 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 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 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 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 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 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 Mollenbeck S Konig 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 lt 63 AID FFJ614 gt 3 0 CO 2 Z 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 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 Balch P A 2002 Prescription for Nutritional Healing the A to Z Guide to Supplements Penguin p 233 ISBN 978 1 58333 143 9 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 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 Retrieved from https en wikipedia org w index php title Eucalyptol amp oldid 1221552598, wikipedia, wiki, book, books, library,

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