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 |
|---|---|---|---|
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 |
|---|---|---|---|---|
| Primary | Helixia Sinus Approved UseUnknown |
|||
| Primary | Helixia Sinus Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
790.75 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866111/ |
4 mL single, respiratory dose: 4 mL route of administration: Respiratory experiment type: SINGLE co-administered: |
EUCALYPTOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
275 ng/mL |
2 mL single, respiratory dose: 2 mL route of administration: Respiratory experiment type: SINGLE co-administered: |
EUCALYPTOL serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
19 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20425757/ |
1.02 mg single, oral dose: 1.02 mg route of administration: Oral experiment type: SINGLE co-administered: |
EUCALYPTOL plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
23076 ng × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866111/ |
4 mL single, respiratory dose: 4 mL route of administration: Respiratory experiment type: SINGLE co-administered: |
EUCALYPTOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
104.6 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/8866111/ |
4 mL single, respiratory dose: 4 mL route of administration: Respiratory experiment type: SINGLE co-administered: |
EUCALYPTOL serum | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
19.9 min |
2 mL single, respiratory dose: 2 mL route of administration: Respiratory experiment type: SINGLE co-administered: |
EUCALYPTOL serum | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/33848890/ |
EUCALYPTOL plasma | Homo sapiens |
Doses
| Dose | Population | Adverse events |
|---|---|---|
200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Other AEs: Nausea, stomach ach... |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Heartburn | 200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
|
| Nausea | 200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
|
| stomach ach | 200 mg 3 times / day multiple, oral Highest studied dose Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes. | 2004-08 |
|
| Chemical composition of the essential oils of two Alpinia species from Hainan Island, China. | 2004-07-10 |
|
| Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice. | 2004-06 |
|
| Effect of monoterpenes on lipid oxidation in maize. | 2004-06 |
|
| Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions. | 2004-05-05 |
|
| Flavor release and perception in hard candy: influence of flavor compound-compound interactions. | 2004-05-05 |
|
| Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae). | 2004-05-05 |
|
| Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis. | 2004-05 |
|
| Constraint of feeding by chronic ingestion of 1,8-cineole in the brushtail possum (Trichosurus vulpecula). | 2004-04 |
|
| Effects of a novel gaseous antioxidative system containing a rosemary extract on the oxidation induced by nitrogen dioxide and ultraviolet radiation. | 2004-04 |
|
| 1,8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis. | 2004-04 |
|
| Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L. | 2004-03-24 |
|
| Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt. | 2004-03 |
|
| Inhibition of acetylcholinesterase by Tea Tree oil. | 2004-03 |
|
| Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay. | 2004-02 |
|
| Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry. | 2004-01-23 |
|
| Transformation of terpenes using a Picea abies suspension culture. | 2004-01-22 |
|
| Characteristics, clinical effect profile and tolerability of a nasal spray preparation of Artemisia abrotanum L. for allergic rhinitis. | 2004-01 |
|
| Chemical and biological evaluation of the essential oils of different Melaleuca species. | 2004-01 |
|
| Antifungal activity of Thymus oils and their major compounds. | 2004-01 |
|
| Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi. | 2003-12 |
|
| Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil. | 2003-12 |
|
| Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities. | 2003-11-19 |
|
| Composition and antimicrobial activity of Achillea clavennae L. essential oil. | 2003-11 |
|
| Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones. | 2003-10-28 |
|
| Effect of nitrogen concentration of the nutrient solution on the volatile constituents of leaves of Salvia fruticosa Mill. in solution culture. | 2003-10-22 |
|
| Essential oils from Mediterranean lamiaceae as weed germination inhibitors. | 2003-10-08 |
|
| 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). | 2003-10 |
|
| Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy. | 2003-10 |
|
| Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases. | 2003-09-15 |
|
| Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth. | 2003-08-27 |
|
| Preferred age for assessment of qualitative and quantitative characteristics of the essential oil of tea tree (Melaleuca alternifolia) seedlings prior to plantation establishment. | 2003-07-16 |
|
| Noninvasive glucose monitoring by back diffusion via skin: chemical and physical enhancements. | 2003-07 |
|
| Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth. | 2003-06-18 |
|
| Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India. | 2003-06 |
|
| Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil. | 2003-06 |
|
| Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana. | 2003-06 |
|
| Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens. | 2003-05-21 |
|
| Antimicrobial and antioxidant activities of three Mentha species essential oils. | 2003-05 |
|
| Near infrared spectroscopy for cost effective screening of foliar oil characteristics in a Melaleuca cajuputi breeding population. | 2003-04-23 |
|
| Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches. | 2003-04-09 |
|
| Essential oils produced by in vitro shoots of sage (Salvia officinalis L.). | 2003-04-09 |
|
| Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. | 2003-03-12 |
|
| Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale. | 2003-03 |
|
| Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings. | 2003-03 |
|
| Odor compound detection in male euglossine bees. | 2003-01 |
|
| 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. | 2003-01 |
|
| Differential metabolism of 1,8-cineole in insects. | 2003-01 |
|
| Erythema multiforme due to contact with weeds: a recurrence after patch testing. | 2003-01 |
|
| Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil. | 2003 |
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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| Record UNII |
RV6J6604TK
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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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1268900
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