أوكاليپتول

(تم التحويل من Eucalyptol)
أوكاليپتول
الأسماء
اسم أيوپاك
1,3,3-Trimethyl-2-oxabicyclo[2,2,2]octane
أسماء أخرى
1,8-Cineole
1,8-Epoxy-p-menthane
المُعرِّفات
رقم CAS
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.757 Edit this at Wikidata
KEGG
UNII
الخصائص
الصيغة الجزيئية C10H18O
كتلة مولية 154.249 گ/مول
الكثافة 0.9225 گ/سم3
نقطة الانصهار
نقطة الغليان
ما لم يُذكر غير ذلك، البيانات المعطاة للمواد في حالاتهم العيارية (عند 25 °س [77 °ف]، 100 kPa).
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مراجع الجدول

الأوكاليپتول Eucalyptol، هو مركب عضوي طبيعي عبارة عن سائل عديم اللون. وهو إثير ومونوترين دوري.

يعرف الأوكاليپتول أيضاً بمرادفات مختلفة: 1، 8-سينيول، كاجپول، 1، 8-إپوكسي-پي-منثان، 1، 8-أكوسيدو-پي-ميثان، الأوكاليپتول، 1، 3، 3-ثلاثي الميثيل-2-أوكسابيسيكلو[2،2،2]اوكتانن سينيول.

عام 1870، حدد ف.س. كلويز وأطلق اسم الأوكاليپتول على الجزء السائد في زيت أوكاليپتوس گلوبولوس.[1] زيت الأوكاليپتوس، هو الاسم العام الذي يطلق على الزيتوت المستخرجة من جنس نباتات الأوكاليپتوس، والتي يجب عدم الخلط بينها وبين مركب الأوكاليپتول الكيميائي.

الاستخدامات

Because of its pleasant, spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics.[2] 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.[2][3] In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes.[4] It is claimed to be added to improve the flavor.[2]

Eucalyptol is an ingredient in commercial mouthwashes and cough suppressants.[2]

غيرهم

Eucalyptol exhibits insecticidal and insect repellent properties.[5][6]

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.[7] 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.[8]

الطبي

يستخدم الأوكاليپتول كمكون ضمن الكثير من أنواع غسولات الفم وأدوية السعال، فضلاً عن كونه مكون غير نشط في بودرة الجسم.


السمية

Eucalyptol has a toxicity (LD50) of 2.48 grams per kg (rat).[2] Ingestion in significant quantities is likely to cause headache and gastric distress, such as nausea and vomiting.[2] 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.[2]

Consequently, eucalyptol should never be ingested unless in highly diluted formulations. Toxicity is significantly reduced when administered topically. However it should not be used topically during pregnancy, breastfeeding, or on children under two.[9]

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.[10][11][12]  ملف:Eucalyptol synthesis.svg


قائمة النباتات التي تحتوي على المادة الكيميائية

الوضع التركيبي

انظر أيضاً

المصادر

  1. ^ Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. p. 6. ISBN 0-909605-69-6.
  2. ^ أ ب ت ث ج ح خ خطأ استشهاد: وسم <ref> غير صحيح؛ لا نص تم توفيره للمراجع المسماة pubchem
  3. ^ Harborne, J. B.; Baxter, H. (30 أغسطس 2001). Chemical Dictionary of Economic Plants. John Wiley & Sons. ISBN 0-471-49226-4.
  4. ^ "Cigarette Ingredients – Chemicals in Cigarettes". New York State Department of Health. Retrieved 28 يوليو 2014.
  5. ^ Klocke, J. A.; Darlington, M. V.; Balandrin, M. F. (ديسمبر 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.
  6. ^ Sfara, V.; Zerba, E. N.; Alzogaray, R. A. (مايو 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ "Eucalyptus Oil: Is it Safe?". www.poison.org (in الإنجليزية). Retrieved 31 مايو 2025.
  10. ^ Rinkel, Jan; Rabe, Patrick; zur Horst, Laura; Dickschat, Jeroen S (4 نوفمبر 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.
  11. ^ Wise, Mitchell L.; Savage, Thomas J.; Katahira, Eva; Croteau, Rodney (12 يونيو 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 (in الإنجليزية). 273 (24): 14891–14899. doi:10.1074/jbc.273.24.14891. ISSN 0021-9258. PMID 9614092.
  12. ^ Croteau, R.; Alonso, W. R.; Koepp, A. E.; Johnson, M. A. (1 فبراير 1994). "Biosynthesis of Monoterpenes: Partial Purification, Characterization, and Mechanism of Action of 1,8-Cineole Synthase". Archives of Biochemistry and Biophysics (in الإنجليزية). 309 (1): 184–192. doi:10.1006/abbi.1994.1101. ISSN 0003-9861. PMID 8117108.
  13. ^ "Cannabis and cannabis extracts: greater than the sum of their parts?". Journal of Cannabis Therapeutics. 1 (3–4): 103–132. 2001. doi:10.1300/J175v01n03_08. Retrieved 20 سبتمبر 2013. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  14. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  15. ^ 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". Veterinary Parasitology. 167 (1): 1–7. doi:10.1016/j.vetpar.2009.09.053. PMID 19896276.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  16. ^ 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.
  17. ^ 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.
  18. ^ 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.
  19. ^ "In-vitro inhibition of human erythrocyte acetylcholinesterase by salvia lavandulaefolia essential oil and constituent terpenes". J Pharm Pharmacol. 52 (7): 895–902. 2000. doi:10.1211/0022357001774598. PMID 10933142. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
  20. ^ Balch, P. A. (2002). Prescription for Nutritional Healing: the A to Z Guide to Supplements. Penguin. p. 233. ISBN 978-1-58333-143-9.
  21. ^ 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  22. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 5 يوليو 2009.
  23. ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). tga.gov.au. Archived from the original (PDF) on 2 يوليو 2009. Retrieved 5 يوليو 2009.

قراءات إضافية

  • Boland, D. J.; Brophy, J. J.; House, A. P. N. (1991). Eucalyptus Leaf Oils: Use, Chemistry, Distillation and Marketing. Melbourne: Inkata Press. ISBN 0-909605-69-6.

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