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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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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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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Syn stereochemistry of cyclic ether formation in 1,8-cineole biosynthesis catalyzed by recombinant synthase from Salvia officinalis. | 2002 Jul 24 |
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Acaricidal activity of pine essential oils and their main components against Tyrophagus putrescentiae, a stored food mite. | 2002 Jul 31 |
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In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. | 2002 Jul 8 |
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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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Main agronomic-productive characteristics of two ecotypes of Rosmarinus officinalis L. and chemical composition of their essential oils. | 2002 Jun 5 |
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Chemical composition and in-vitro antimicrobial activity of the essential oils of three Greek Achillea species. | 2002 Mar-Apr |
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Antimicrobial properties of the essential oil of Artemisia asiatica Nakai. | 2002 May |
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Microsomal metabolism and enzyme kinetics of the terpene p-cymene in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus) and rat. | 2002 May |
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Compositions and the in vitro antimicrobial activities of the essential oils of Achillea setacea and Achillea teretifolia (Compositae). | 2002 Nov |
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Application of solid-phase microextraction to the quantitative analysis of 1,8-cineole in blood and expired air in a Eucalyptus herbivore, the brushtail possum (Trichosurus vulpecula). | 2002 Nov 25 |
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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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Near infrared spectroscopy for cost effective screening of foliar oil characteristics in a Melaleuca cajuputi breeding population. | 2003 Apr 23 |
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Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches. | 2003 Apr 9 |
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Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). | 2003 Apr 9 |
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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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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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Noninvasive glucose monitoring by back diffusion via skin: chemical and physical enhancements. | 2003 Jul |
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Preferred age for assessment of qualitative and quantitative characteristics of the essential oil of tea tree (Melaleuca alternifolia) seedlings prior to plantation establishment. | 2003 Jul 16 |
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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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Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana. | 2003 Jun |
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Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth. | 2003 Jun 18 |
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Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale. | 2003 Mar |
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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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Antimicrobial and antioxidant activities of three Mentha species essential oils. | 2003 May |
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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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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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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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1,8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis. | 2004 Apr |
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Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes. | 2004 Aug |
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Characteristics, clinical effect profile and tolerability of a nasal spray preparation of Artemisia abrotanum L. for allergic rhinitis. | 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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Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice. | 2004 Jun |
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Effect of monoterpenes on lipid oxidation in maize. | 2004 Jun |
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Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt. | 2004 Mar |
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Inhibition of acetylcholinesterase by Tea Tree oil. | 2004 Mar |
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Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L. | 2004 Mar 24 |
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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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Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis. | 2004 May |
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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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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ACTIVE MOIETY