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?
Molecular Formula | C10H18O |
Molecular Weight | 154.2493 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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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The water-soluble components of the essential oil of Melaleuca alternifolia (tea tree oil) suppress the production of superoxide by human monocytes, but not neutrophils, activated in vitro. | 2001 Apr |
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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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Volatile essential oil constituents of Alpinia smithiae (Zingiberaceae). | 2001 Jun |
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Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. | 2001 Mar |
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Essential oils from Azorean Laurus azorica. | 2001 May |
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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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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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Monoterpenoid accumulation in Melaleuca alternifolia seedlings. | 2002 Apr |
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Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals. | 2002 Dec |
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Cardiovascular effects of 1,8-cineole, a terpenoid oxide present in many plant essential oils, in normotensive rats. | 2002 Dec |
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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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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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Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae). | 2002 May |
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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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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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Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi. | 2003 Dec |
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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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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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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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Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry. | 2004 Jan 23 |
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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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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.
Substance Class |
Chemical
Created
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admin
on
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Fri Dec 15 15:54:35 GMT 2023
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on
Fri Dec 15 15:54:35 GMT 2023
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Record UNII |
RV6J6604TK
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Record Status |
Validated (UNII)
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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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R05CA13
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EUCALYPTOL
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PARENT -> CONSTITUENT MAY BE PRESENT |
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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