Eucalyptol
Identification
- Name
- Eucalyptol
- Accession Number
- DB03852 (EXPT00969)
- Type
- Small Molecule
- Groups
- Experimental, Nutraceutical
- 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.
- Structure
- Synonyms
- 1,8-cineol
- 1,8-Cineole
- 1,8-epoxy-p-menthane
- 1,8-oxido-p-menthane
- Cajeputol
- Cineole
- Eucalyptol
- Zineol
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End 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 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 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 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 Antiseptic Eucalyptol (.092 kg/100L) + Levomenthol (.042 kg/100L) + Menthyl salicylate (.060 kg/100L) + Thymol (.064 kg/100L) Mouthwash Oral Duane Reade 2006-08-08 Not applicable US 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
- 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
- UNII
- RV6J6604TK
- CAS number
- 470-82-6
- Weight
- Average: 154.2493
Monoisotopic: 154.135765198 - Chemical Formula
- C10H18O
- 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
Pharmacology
- Indication
- Not Available
- Associated Conditions
- Pharmacodynamics
- Not Available
- Mechanism of action
- Not Available
- Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Route of elimination
- Not Available
- Half life
- Not Available
- Clearance
- Not Available
- Toxicity
Oral, rat LD50: 2480 mg/kg
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.
Learn moreStructured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.
Learn moreStructured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.
Learn moreInteractions
- 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
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
- ChEBI
- 27961
- ChEMBL
- CHEMBL1231862
- PharmGKB
- PA449555
- Guide to Pharmacology
- GtP Drug Page
- HET
- CNL
- Wikipedia
- Eucalyptol
- ATC Codes
- R05CA13 — Cineole
- 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
Taxonomy
- 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
- Oxane / Oxacycle / Ether / Dialkyl ether / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Aliphatic heteropolycyclic compound
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- cineole (CHEBI:27961)
Drug created on June 13, 2005 07:24 / Updated on December 02, 2019 06:41