Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@@H](CC1)C(C)(C)O2
InChI
InChIKey=WEEGYLXZBRQIMU-LUYSIGKXSA-N
InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10?
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20359267 | https://www.ncbi.nlm.nih.gov/pubmed/27771935 | https://www.ncbi.nlm.nih.gov/pubmed/27722047 | https://www.ncbi.nlm.nih.gov/pubmed/27251496 | https://www.ncbi.nlm.nih.gov/pubmed/19624838 | https://www.ncbi.nlm.nih.gov/pubmed/26207629
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20359267 | https://www.ncbi.nlm.nih.gov/pubmed/27771935 | https://www.ncbi.nlm.nih.gov/pubmed/27722047 | https://www.ncbi.nlm.nih.gov/pubmed/27251496 | https://www.ncbi.nlm.nih.gov/pubmed/19624838 | https://www.ncbi.nlm.nih.gov/pubmed/26207629
Eucalyptol is a natural organic compound with fresh mint-like smell and a spicy, cooling taste. Eucalyptol comprises up to 90 percent of the essential oil of some species of the generic product Eucalyptus oil, hence the common name of the compound. It is also found in camphor laurel, bay leaves, tea tree, mugwort, sweet basil, wormwood, rosemary, common sage, 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. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant, as well as an inactive ingredient in body powder.
The typical concentrations of eucalyptol in cosmetic products have been reported to be 1.6% in perfume, 0.4% in soap, 0.1% in creams and lotions and 0.04% in detergents. Committee of Experts on Flavouring Substances of the Council of Europe (CEFS) proposed upper levels of 0.1 mg/kg in beverages and 5 mg/kg in food with the exception of 15 mg/kg in candy and confectionery and 50 mg/kg in alcoholic beverages. Eucalyptol controls airway mucus hypersecretion and asthma via anti-inflammatory cytokine inhibition. Eucalyptol is an effective treatment for nonpurulent rhinosinusitis. Eucalyptol reduces inflammation and pain when applied topically.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0032640 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15477123 |
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Target ID: GO:0032611 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15477123 |
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Target ID: GO:0032633 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15477123 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Helixia Sinus Approved UseUnknown |
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Primary | Helixia Sinus Approved UseUnknown |
PubMed
Title | Date | PubMed |
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A rapid method for evaluating microbicidal activity of dentifrice formulations against salivary bacteria ex vivo. | 2000 |
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Biotransformation of 1,8-cineole by human liver microsomes. | 2001 |
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In vitro activity of tea tree oil against Candida albicans mycelial conversion and other pathogenic fungi. | 2001 Aug |
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Toxicity, feeding deterrence, and effect of activity of 1,8-cineole from Artemisia annua on progeny production of Tribolium castanaeum (Coleoptera: Tenebrionidae). | 2001 Aug |
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Essential oil composition and antimicrobial activity of three Zingiberaceae from S.Tomé e Príncipe. | 2001 Aug |
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Ambulation-promoting effect of peppermint oil and identification of its active constituents. | 2001 Jul-Aug |
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Volatile essential oil constituents of Alpinia smithiae (Zingiberaceae). | 2001 Jun |
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Antibacterial activity of Salvia tomentosa essential oil. | 2001 Nov |
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Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. | 2001 Nov |
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Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes. | 2001 Oct |
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Effect of passive and iontophoretic skin pretreatments with terpenes on the in vitro skin transport of piroxicam. | 2001 Oct 23 |
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Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures. | 2001 Sep |
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Antipredator defense of biological control agent Oxyops vitiosa is mediated by plant volatiles sequestered from the host plant Melaleuca quinquenervia. | 2002 Feb |
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Volatile oil comparison of cotyledon leaves of chemotypes of Melaleuca alternifolia. | 2002 Feb |
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Sensitive indoor air monitoring of monoterpenes using different adsorbents and thermal desorption gas chromatography with mass-selective detection. | 2002 Jul 12 |
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Composition and antimicrobial activity of essential oil and hexane-ether extract of Tanacetum santolinoides (dc.) Feinbr. and Fertig. | 2002 Jul-Aug |
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Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line. | 2002 Jul-Aug |
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Stomatal constraints may affect emission of oxygenated monoterpenoids from the foliage of Pinus pinea. | 2002 Nov |
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Antifungal activities of selected aromatic plants growing wild in Greece. | 2002 Oct |
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Possible role of mast cells in cineole-induced scratching behavior in mice. | 2002 Oct |
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Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil. | 2003 |
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Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth. | 2003 Aug 27 |
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Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi. | 2003 Dec |
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Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil. | 2003 Dec |
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Odor compound detection in male euglossine bees. | 2003 Jan |
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Dietary influences on terpenoids sequestered by the biological control agent Oxyops vitiosa: effect of plant volatiles from different Melaleuca quinquenervia chemotypes and laboratory host species. | 2003 Jan |
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Erythema multiforme due to contact with weeds: a recurrence after patch testing. | 2003 Jan |
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Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India. | 2003 Jun |
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Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil. | 2003 Jun |
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Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. | 2003 Mar 12 |
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Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens. | 2003 May 21 |
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Composition and antimicrobial activity of Achillea clavennae L. essential oil. | 2003 Nov |
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Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities. | 2003 Nov 19 |
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The effects of Eucalyptus terpenes on hepatic cytochrome P450 CYP4A, peroxisomal Acyl CoA oxidase (AOX) and peroxisome proliferator activated receptor alpha (PPARalpha) in the common brush tail possum (Trichosurus vulpecula). | 2003 Oct |
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Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy. | 2003 Oct |
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Effect of nitrogen concentration of the nutrient solution on the volatile constituents of leaves of Salvia fruticosa Mill. in solution culture. | 2003 Oct 22 |
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Essential oils from Mediterranean lamiaceae as weed germination inhibitors. | 2003 Oct 8 |
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Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases. | 2003 Sep 15 |
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Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones. | 2003 Sep-Oct |
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Constraint of feeding by chronic ingestion of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). | 2004 Apr |
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Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. | 2004 Feb |
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Chemical and biological evaluation of the essential oils of different Melaleuca species. | 2004 Jan |
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Antifungal activity of Thymus oils and their major compounds. | 2004 Jan |
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Transformation of terpenes using a Picea abies suspension culture. | 2004 Jan 22 |
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Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry. | 2004 Jan 23 |
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Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice. | 2004 Jun |
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Chemical composition of the essential oils of two Alpinia species from Hainan Island, China. | 2004 Mar-Apr |
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Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions. | 2004 May 5 |
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Flavor release and perception in hard candy: influence of flavor compound-compound interactions. | 2004 May 5 |
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Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae). | 2004 May 5 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19624838
In this double-blind, placebo-controlled multi-center-study we randomly assigned 242 patients with stable COPD to receive 200 mg of cineole or placebo 3 times daily as concomitant therapy for 6 months
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27251496
Cell viability was determined by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay. BEAS-2B cells were treated with 0.1, 1, 10 µg/mL 1.8-cineole (Eucalyptol) for 24 h, and then incubated with MTT (0.5 mg/mL) at 37°C for 4 h. The viable cell number was directly proportional to the production of formazan, which was dissolved in isopropanol and determined by measuring the absorbance at 570 nm using a microplate reader.
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 172.515
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WHO-VATC |
QR05CA13
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JECFA EVALUATION |
EUCALYPTOL
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NCI_THESAURUS |
C74536
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WHO-ATC |
R05CA13
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EUCALYPTOL
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M5208
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ACTIVE MOIETY