Eucalyptol

Identification

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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

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MOLSDFPDBSMILESInChI

Similar Structures

Structure for Eucalyptol (DB03852)

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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
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Rosatra Synergy for treatment of Acne Rosacea	Oil	0.7 g/50g	Topical	Phytopia Co., Ltd.	2016-02-29	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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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
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
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
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
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
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
Alsirub Ont	Eucalyptol (2.5 %) + Levomenthol (4 %) + Methyl salicylate (7.5 %)	Ointment	Topical	Alsi Cie Ltee	1977-12-31	2003-05-21
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
Amber Mouth Wash - Liq	Eucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %)	Liquid	Dental	Perrigo International	1996-10-09	1999-08-06
Amber Mouthwash - Liq	Eucalyptol (0.092 %) + Levomenthol (0.042 %) + Thymol (0.064 %)	Liquid	Dental	Perrigo International	1996-06-30	1999-08-06

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
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

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

• Gingivitis

Pharmacodynamics

Not Available

Mechanism of action

Not Available

Unlock Additional Data

Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured 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.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

• Eucalyptol
  2alpha-hydroxy-1,8-cineole
• Eucalyptol
  3alpha-hydroxy-1,8-cineole

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

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

References

General References

1. 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

RxNav

21116

ChEBI

27961

ChEMBL

CHEMBL1231862

PharmGKB

PA449555

Guide to Pharmacology

GtP Drug Page

PDBe Ligand

CNL

Wikipedia

Eucalyptol

ATC Codes

R05CA13 — Cineole

• R05CA — Expectorants
• R05C — EXPECTORANTS, EXCL. COMBINATIONS WITH COUGH SUPPRESSANTS
• R05 — COUGH AND COLD PREPARATIONS
• R — RESPIRATORY SYSTEM

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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

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)

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Drug created on June 13, 2005 07:24 / Updated on February 06, 2020 11:50