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Eucalyptol
Eucalyptol
is a natural organic compound that is a colorless liquid. It is a cyclic ether and a monoterpenoid. Eucalyptol
Eucalyptol
is also known by a variety of synonyms: 1,8-cineol, 1,8-cineole, cajeputol, 1,8-epoxy-p-menthane, 1,8-oxido-p-menthane, eucalyptol, eucalyptole, 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane, cineol, cineole. In 1870, F. S. Cloez identified and ascribed the name eucalyptol to the dominant portion of Eucalyptus globulus
Eucalyptus globulus
oil.[1]

Contents

1 Composition 2 Properties 3 Uses

3.1 Flavoring and fragrance 3.2 Medicinal 3.3 Insecticide
Insecticide
and repellent

4 Toxicology 5 List of plants that contain the chemical 6 Compendial status

6.1 Sulfonation

7 See also 8 References 9 Further reading 10 External links

Composition[edit] Eucalyptol
Eucalyptol
comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus
Eucalyptus
oil,[1] hence the common name of the compound. It is also found in camphor laurel, bay leaves, tea tree, sweet basil,[citation needed] wormwood, rosemary, common sage, Cannabis sativa
Cannabis sativa
and other aromatic plant foliage. Eucalyptol with a purity from 99.6 to 99.8 percent can be obtained in large quantities by fractional distillation of eucalyptus oil. Although it can be used internally as a flavoring and medicine ingredient at very low doses, typical of many essential oils (volatile oils), eucalyptol is toxic if ingested at higher than normal doses.[2] Properties[edit] Eucalyptol
Eucalyptol
has a fresh mint-like smell and a spicy, cooling taste. It is insoluble in water, but miscible with ether, ethanol, and chloroform. The boiling point is 176 °C and the flash point is 49 °C. Eucalyptol
Eucalyptol
forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts are useful for purification. Uses[edit] Flavoring and fragrance[edit] Because of its pleasant spicy aroma and taste, eucalyptol is used in flavorings, fragrances, and cosmetics. Cineole-based eucalyptus oil is used as a flavouring at low levels (0.002%) in various products, including baked goods, confectionery, meat products and beverages.[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 that it is added to improve the flavor. Medicinal[edit] Eucalyptol
Eucalyptol
is an ingredient in many brands of mouthwash and cough suppressant, as well as an inactive ingredient in body powder. Insecticide
Insecticide
and repellent[edit] Eucalyptol
Eucalyptol
is used as an insecticide and insect repellent.[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 non-social 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] Toxicology[edit] In higher-than-normal doses, eucalyptol is hazardous via ingestion, skin contact, or inhalation. It can have acute health effects on behavior, respiratory tract, and nervous system. The acute oral LD50 is 2480 mg/kg (rat). It is classified as a reproductive toxin for females and a suspected reproductive toxin for males.[2] List of plants that contain the chemical[edit]

Cannabis[9] Cinnamomum camphora, camphor laurel (50%)[10] Eucalyptus
Eucalyptus
cneorifolia[citation needed] Eucalyptus
Eucalyptus
dives[citation needed] Eucalyptus
Eucalyptus
dumosa[citation needed] Eucalyptus
Eucalyptus
globulus[11] Eucalyptus
Eucalyptus
goniocalyx[citation needed] Eucalyptus
Eucalyptus
horistes[citation needed] Eucalyptus
Eucalyptus
kochii[citation needed] Eucalyptus
Eucalyptus
leucoxylon[citation needed] Eucalyptus
Eucalyptus
oleosa[citation needed] Eucalyptus
Eucalyptus
polybractea[citation needed] Eucalyptus
Eucalyptus
radiata[citation needed] Eucalyptus
Eucalyptus
rossii[citation needed] Eucalyptus
Eucalyptus
sideroxylon[citation needed] Eucalyptus
Eucalyptus
smithii[citation needed] Eucalyptus
Eucalyptus
staigeriana[12] Eucalyptus
Eucalyptus
tereticornis[citation needed] Eucalyptus
Eucalyptus
viridis[citation needed] Hedychium coronarium, butterfly lily[13][14][15][16] Helichrysum gymnocephalum[17] Kaempferia galanga, galangal, (5.7%)[18] Laurus nobilis, bay laurel, (45%)[citation needed] Melaleuca alternifolia, tea tree, (0–15%)[citation needed] Salvia lavandulifolia, Spanish sage (13%)[19] Turnera diffusa, damiana[20] Umbellularia californica, pepperwood (22.0%)[21] Zingiber officinale, ginger[citation needed]

Compendial status[edit]

British Pharmacopoeia[22] Martindale: The Extra Pharmacopoeia 31[23]

N.B. Listed as "cineole" in some pharmacopoeias. Sulfonation[edit]

Sulfonation
Sulfonation
of eucalyptol with SO3 in the presence of dioxane gives good analeptic/antiseptic agents.[24]

See also[edit]

Camphor Citral Eucalyptus
Eucalyptus
oil Lavender Menthol Mouthwash

References[edit]

^ 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. ISBN 0-909605-69-6.  ^ a b "Material Safety Data Sheet – Cineole". ScienceLab. Retrieved 2012-09-27.  ^ Harborne, J. B.; Baxter, H. Chemical Dictionary of Economic Plants. ISBN 0-471-49226-4.  ^ "Cigarette Ingredients – Chemicals in Cigarettes". New York State Department of Health. Retrieved 28 July 2014.  ^ 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. doi:10.1007/BF01012562.  ^ 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. PMID 19496421.  ^ 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. PMID 12647866.  ^ Schemske, Douglas W.; Lande, Russell (1984). "Fragrance collection and territorial display by male orchid bees". Animal
Animal
Behaviour. 32 (3): 935–937. doi:10.1016/s0003-3472(84)80184-0.  ^ McPartland, J. M.; Russo, E. B. (2001). " Cannabis
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.  ^ 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
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.  ^ Gilles, M.; Zhao, J.; An, M.; Agboola, S. (2010). "Chemical Composition and Antimicrobial Properties of Essential Oils of three Australian Eucalyptus
Eucalyptus
Species". Food Chemistry. 119 (2): 731–737. doi:10.1016/j.foodchem.2009.07.021.  ^ 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.  ^ Joy, B.; Rajan, A.; Abraham, E. (2007). "Antimicrobial Activity and Chemical Composition of Essential Oil from Hedychium coronarium". Phytotherapy Research. 21: 439–443. doi:10.1002/ptr.2091.  ^ Martins, M.; Caravante, A.; Appezzato-Da-Glória, B.; Soares, M.; Moreira, R.; Santos, L. (2010). "Anatomical characterization and phytochemistry of leaves and rhizomes of Hedychium coronarium
Hedychium coronarium
J. König (Zingiberaceae)". Rev. Bras. Plantas Med. 12 (2): 179–187. doi:10.1590/s1516-05722010000200009.  ^ Santos, S. B.; Pedralli, G.; Meyer, S. T. (2005). "Aspectos da fenologia e ecologia de Hedychium coronarium
Hedychium coronarium
(Zingiberaceae) na estação ecológica do Tripuí, Ouro Preto MG". Planta Daninha (in Portuguese). 23 (2): 175–180. doi:10.1590/s0100-83582005000200002.  ^ 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.  ^ Wong, K. C.; Ong, K. S.; Lim, C. L. (2006). "Composition of the Essential Oil of Rhizomes of Kaempferia galanga
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.  ^ 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.  ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 5 July 2009.  ^ Therapeutic Goods Administration. "Chemical Substances" (PDF). tga.gov.au. Archived from the original (PDF) on 2 July 2009. Retrieved 5 July 2009.  ^ U.S. Patent 3,397,212 eidem DE 1296646 

Further reading[edit]

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

External links[edit]

"Eucalyptus". Botanical.com.  "Oleum Eucalypti, B.P. Oil of Eucalyptus". Henriette's Herbal.  "MSDS – Safety data for eucalyptol". Oxford University Chemistry Department. [dead link]

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TRPA

Activators

4-Hydroxynonenal 4-Oxo-2-nonenal 4,5-EET 12S-HpETE 15-Deoxy-Δ12,14-prostaglandin J2 α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Acrolein Allicin
Allicin
(garlic) Allyl isothiocyanate
Allyl isothiocyanate
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Cannabichromene
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Cannabigerol
(cannabis) Cinnamaldehyde
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Curcumin
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( Lindera
Lindera
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Linalool
(Sichuan pepper, thyme) Methylglyoxal Methyl salicylate
Methyl salicylate
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Oleocanthal
(olive oil) Paclitaxel
Paclitaxel
(Pacific yew) Paracetamol
Paracetamol
(acetaminophen) PF-4840154 Phenacyl chloride Polygodial
Polygodial
(Dorrigo pepper) Shogaols (ginger, Sichuan and melegueta peppers) Tear gases Tetrahydrocannabinol
Tetrahydrocannabinol
(cannabis) Thiopropanal S-oxide
Thiopropanal S-oxide
(onion) Umbellulone
Umbellulone
(Umbellularia californica) WIN 55,212-2

Blockers

Dehydroligustilide (celery) Nicotine
Nicotine
(tobacco) Ruthenium red

TRPC

Activators

Adhyperforin
Adhyperforin
(St John's wort) Diacyl glycerol GSK1702934A Hyperforin
Hyperforin
(St John's wort) Substance P

Blockers

DCDPC DHEA-S Flufenamic acid GSK417651A GSK2293017A Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid Niflumic acid Pregnenolone sulfate Progesterone Pyr3 Tolfenamic acid

TRPM

Activators

ADP-ribose BCTC Calcium
Calcium
(intracellular) Cold Coolact P Cooling Agent 10 CPS-369 Eucalyptol
Eucalyptol
(eucalyptus) Frescolat MGA Frescolat ML Geraniol Hydroxycitronellal Icilin Linalool Menthol
Menthol
(mint) PMD 38 Pregnenolone sulfate Rutamarin (Ruta graveolens) Steviol glycosides (e.g., stevioside) (Stevia rebaudiana) Sweet tastants (e.g., glucose, fructose, sucrose; indirectly) Thio-BCTC WS-3 WS-12 WS-23

Blockers

Capsazepine Clotrimazole DCDPC Flufenamic acid Meclofenamic acid Mefenamic acid N-(p-amylcinnamoyl)anthranilic acid Nicotine
Nicotine
(tobacco) Niflumic acid Ruthenium red Rutamarin (Ruta graveolens) Tolfenamic acid TPPO

TRPML

Activators

MK6-83 PI(3,5)P2 SF-22

TRPP

Activators

Triptolide
Triptolide
(Tripterygium wilfordii)

Blockers

Ruthenium red

TRPV

Activators

2-APB 5',6'-EET 9-HODE 9-oxoODE 12S-HETE 12S-HpETE 13-HODE 13-oxoODE 20-HETE α- Sanshool
Sanshool
(ginger, Sichuan and melegueta peppers) Allicin
Allicin
(garlic) AM404 Anandamide Bisandrographolide (Andrographis paniculata) Camphor
Camphor
(camphor laurel, rosemary, camphorweed, African blue basil, camphor basil) Cannabidiol
Cannabidiol
(cannabis) Cannabidivarin
Cannabidivarin
(cannabis) Capsaicin
Capsaicin
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Carvacrol
(oregano, thyme, pepperwort, wild bergamot, others) DHEA Diacyl glycerol Dihydrocapsaicin
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Eugenol
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Evodiamine
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Homocapsaicin
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(chili pepper) Incensole
Incensole
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Menthol
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Nordihydrocapsaicin
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Paclitaxel
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Piperine
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Polygodial
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(RTX) (Euphorbia resinifera/pooissonii) Shogaols (ginger, Sichuan and melegueta peppers) Tetrahydrocannabivarin
Tetrahydrocannabivarin
(cannabis) Thymol
Thymol
(thyme, oregano) Tinyatoxin
Tinyatoxin
(Euphorbia resinifera/pooissonii) Tramadol Vanillin
Vanillin
(vanilla) Zucapsaicin

Blockers

α- Spinasterol
Spinasterol
( Vernonia
Vernonia
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(cannabis) Cannabigerolic acid (cannabis) Cannabigerovarin (cannabis) Cannabinol
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(cannabis) Capsazepine DCDPC DHEA DHEA-S Flufenamic acid GRC-6211 HC-067047 Lanthanum Meclofenamic acid N-(p-amylcinnamoyl)anthranilic acid NGD-8243 Niflumic acid Pregnenolone sulfate RN-1734 RN-9893 Ruthenium red SB-705498 Tivanisiran Tolfenamic acid

See also: Receptor/signaling modulators • Ion channe

.