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 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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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 |
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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 |
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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 |
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Essential oil composition and antimicrobial activity of three Zingiberaceae from S.Tomé e Príncipe. | 2001 Aug |
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Metabolites of dietary 1,8-cineole in the male koala (Phascolarctos cinereus). | 2001 Aug |
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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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Volatile oil comparison of cotyledon leaves of chemotypes of Melaleuca alternifolia. | 2002 Feb |
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Correlation between chemical composition and antibacterial activity of essential oils of some aromatic medicinal plants growing in the Democratic Republic of Congo. | 2002 Feb |
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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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In vitro evaluation of nimodipine permeation through human epidermis using response surface methodology. | 2002 Jul 8 |
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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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Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae). | 2002 May |
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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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Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth. | 2003 Aug 27 |
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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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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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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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Effect of monoterpenes on lipid oxidation in maize. | 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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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.
Substance Class |
Chemical
Created
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on
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Record UNII |
RV6J6604TK
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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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WHO-ATC |
R05CA13
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EUCALYPTOL
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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