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Eucalyptol
Identification
- Name
- Eucalyptol
- Accession Number
- DB03852
- Description
Eucalyptol is naturally produced cyclic ether and monoterpenoid. Eucalyptol is an ingredient in many brands of mouthwash and cough suppressant. It 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. It kills leukaemia cells in vitro.
- Type
- Small Molecule
- Groups
- Experimental, Nutraceutical
- Structure
Structure for Eucalyptol (DB03852)
- Weight
- Average: 154.2493
Monoisotopic: 154.135765198 - Chemical Formula
- C10H18O
- Synonyms
- 1,8-cineol
- 1,8-Cineole
- 1,8-epoxy-p-menthane
- 1,8-oxido-p-menthane
- Cajeputol
- Cineole
- Eucalyptol
- Zineol
Pharmacology
- Indication
- Not Available
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
- Not Available
- Mechanism of action
- Not Available
- Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Oral, rat LD50: 2480 mg/kg
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataRosatra Synergy for treatment of Acne Rosacea Oil 0.7 g/50g Topical Phytopia Co., Ltd. 2016-02-29 Not applicable US 
Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Advanced Antiseptic Eucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Demoulas Supermarkets, Inc. 2010-07-22 Not applicable US Advanced Antiseptic Eucalyptol (.042 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L) Mouthwash Oral Wakfern Food Corporation 2010-11-24 Not applicable US Advanced Antiseptic Citrus Eucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L) Mouthwash Oral Drug Mart 1991-06-15 Not applicable US Advanced Antiseptic Citrus Eucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.042 mL/100L) Mouthwash Oral H.E.B. 2010-10-15 Not applicable US Advanced Citrus Eucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Walmart Stores 2010-07-22 Not applicable US Advanced Citrus Antiseptic Eucalyptol (.092 mL/100L) + Levomenthol (.042 mL/100L) + Methyl salicylate (.060 mL/100L) + Thymol (.064 mL/100L) Mouthwash Oral Publix Supermarkets, Inc. 2001-05-03 Not applicable US Alsirub Ont Eucalyptol (2.5 %) + Levomenthol (4 %) + Methyl salicylate (7.5 %) Ointment Topical Alsi Cie Ltee 1977-12-31 2003-05-21 Canada 
Amber Mouth Rinse Eucalyptol (0.92 mg/1mL) + Levomenthol (0.42 mg/1mL) + Methyl salicylate (0.6 mg/1mL) + Thymol (0.64 mg/1mL) Liquid Oral Filo America 2013-07-30 Not applicable US Amber Mouth Wash - Liq Eucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %) Liquid Dental Perrigo International 1996-10-09 1999-08-06 Canada Amber Mouthwash - Liq Eucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %) Liquid Dental Perrigo International 1996-06-30 1999-08-06 Canada - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antiseptic Rinse Eucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Methyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Meijer 2006-08-08 Not applicable US
Categories
- ATC Codes
- R05CA13 — Cineole
- Drug Categories
- Agrochemicals
- Alcohols
- Anti-Infective Agents
- Antitussive Agents
- Central Nervous System Agents
- Compounds used in a research, industrial, or household setting
- Cosmetics
- Cough and Cold Preparations
- Cyclohexanes
- Cyclohexanols
- Cycloparaffins
- Diet, Food, and Nutrition
- Expectorants
- Fatty Alcohols
- Flavoring Agents
- Food
- Food Additives
- Food and Beverages
- Food Ingredients
- Hexanols
- Household Products
- Insect Repellents
- Lipids
- Monoterpenes
- Mouthwashes
- Pesticides
- Pharmaceutic Aids
- Pharmaceutical Preparations
- Physiological Phenomena
- Protective Agents
- Respiratory System Agents
- Solvents
- Terpenes
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as oxanes. These are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Oxanes
- Sub Class
- Not Available
- Direct Parent
- Oxanes
- Alternative Parents
- Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
- Substituents
- Aliphatic heteropolycyclic compound / Dialkyl ether / Ether / Hydrocarbon derivative / Organic oxygen compound / Organooxygen compound / Oxacycle / Oxane
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cineole (CHEBI:27961)
Chemical Identifiers
- UNII
- RV6J6604TK
- CAS number
- 470-82-6
- InChI Key
- WEEGYLXZBRQIMU-WAAGHKOSSA-N
- InChI
- InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3/t8-,10+
- IUPAC Name
- (1s,4s)-1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
- SMILES
- C[C@@]12CC[C@@H](CC1)C(C)(C)O2
References
- General References
- Bastos VP, Gomes AS, Lima FJ, Brito TS, Soares PM, Pinho JP, Silva CS, Santos AA, Souza MH, Magalhaes PJ: Inhaled 1,8-cineole reduces inflammatory parameters in airways of ovalbumin-challenged Guinea pigs. Basic Clin Pharmacol Toxicol. 2011 Jan;108(1):34-9. doi: 10.1111/j.1742-7843.2010.00622.x. Epub 2010 Aug 16. [PubMed:20722639]
- External Links
- KEGG Drug
- D04115
- KEGG Compound
- C09844
- PubChem Compound
- 2758
- PubChem Substance
- 46506161
- ChemSpider
- 21111689
- 21116
- ChEBI
- 27961
- ChEMBL
- CHEMBL1231862
- PharmGKB
- PA449555
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- CNL
- Wikipedia
- Eucalyptol
- PDB Entries
- 1t2b / 3be0 / 4fmx / 4fyz / 4l6g / 4l77 / 4lht
- MSDS
- Download (74.3 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Coughing 1 Not Available Recruiting Treatment Periodontitis / Type 2 Diabetes Mellitus 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Dental Rinse Oral Mouthwash Oral Mouthwash Buccal Ointment Nasal Lotion Topical Spray Topical Powder Topical Liquid Topical Cream Topical Ointment Topical Mouthwash Buccal; Oral Liquid Intramuscular Suppository Rectal Lozenge Oral Mouthwash Dental; Oral Liquid Oral Emulsion Topical Oil Topical 0.7 g/50g Oil Topical Mouthwash Dental Liquid Respiratory (inhalation) - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 1.5 °C PhysProp boiling point (°C) 176.4 °C PhysProp water solubility 3500 mg/L (at 21 °C) YALKOWSKY,SH & DANNENFELSER,RM (1992) logP 2.74 GRIFFIN,S ET AL. (1999) - Predicted Properties
Property Value Source Water Solubility 0.0225 mg/mL ALOGPS logP 3.36 ALOGPS logP 2.35 ChemAxon logS -3.8 ALOGPS pKa (Strongest Basic) -4.2 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 9.23 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 45.86 m3·mol-1 ChemAxon Polarizability 18.54 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.988 Blood Brain Barrier + 0.9842 Caco-2 permeable + 0.7609 P-glycoprotein substrate Substrate 0.5435 P-glycoprotein inhibitor I Non-inhibitor 0.6374 P-glycoprotein inhibitor II Non-inhibitor 0.6455 Renal organic cation transporter Non-inhibitor 0.7847 CYP450 2C9 substrate Non-substrate 0.8132 CYP450 2D6 substrate Non-substrate 0.7839 CYP450 3A4 substrate Substrate 0.5962 CYP450 1A2 substrate Non-inhibitor 0.7719 CYP450 2C9 inhibitor Non-inhibitor 0.7571 CYP450 2D6 inhibitor Non-inhibitor 0.95 CYP450 2C19 inhibitor Non-inhibitor 0.658 CYP450 3A4 inhibitor Non-inhibitor 0.9395 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9399 Ames test Non AMES toxic 0.9574 Carcinogenicity Non-carcinogens 0.7856 Biodegradation Not ready biodegradable 0.8549 Rat acute toxicity 1.8144 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8743 hERG inhibition (predictor II) Non-inhibitor 0.7089
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-0536-9200000000-aa52695ff4a2c1313e0b Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable
Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52
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