U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of EUCALYPTOL

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?

HIDE SMILES / InChI

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Helixia Sinus

Approved Use

Unknown
Primary
Helixia Sinus

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A rapid method for evaluating microbicidal activity of dentifrice formulations against salivary bacteria ex vivo.
2000
Biotransformation of 1,8-cineole by human liver microsomes.
2001
In vitro activity of tea tree oil against Candida albicans mycelial conversion and other pathogenic fungi.
2001 Aug
Toxicity, feeding deterrence, and effect of activity of 1,8-cineole from Artemisia annua on progeny production of Tribolium castanaeum (Coleoptera: Tenebrionidae).
2001 Aug
Essential oil composition and antimicrobial activity of three Zingiberaceae from S.Tomé e Príncipe.
2001 Aug
Ambulation-promoting effect of peppermint oil and identification of its active constituents.
2001 Jul-Aug
Volatile essential oil constituents of Alpinia smithiae (Zingiberaceae).
2001 Jun
Antibacterial activity of Salvia tomentosa essential oil.
2001 Nov
Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential.
2001 Nov
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
Effect of passive and iontophoretic skin pretreatments with terpenes on the in vitro skin transport of piroxicam.
2001 Oct 23
Eucalyptus camaldulensis: volatiles from immature flowers and high production of 1,8-cineole and beta-pinene by in vitro cultures.
2001 Sep
Antipredator defense of biological control agent Oxyops vitiosa is mediated by plant volatiles sequestered from the host plant Melaleuca quinquenervia.
2002 Feb
Volatile oil comparison of cotyledon leaves of chemotypes of Melaleuca alternifolia.
2002 Feb
Sensitive indoor air monitoring of monoterpenes using different adsorbents and thermal desorption gas chromatography with mass-selective detection.
2002 Jul 12
Composition and antimicrobial activity of essential oil and hexane-ether extract of Tanacetum santolinoides (dc.) Feinbr. and Fertig.
2002 Jul-Aug
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
Stomatal constraints may affect emission of oxygenated monoterpenoids from the foliage of Pinus pinea.
2002 Nov
Antifungal activities of selected aromatic plants growing wild in Greece.
2002 Oct
Possible role of mast cells in cineole-induced scratching behavior in mice.
2002 Oct
Antifungal activity of the components of Melaleuca alternifolia (tea tree) oil.
2003
Supercritical carbon dioxide extraction of essential oils from Perovskia atriplicifolia Benth.
2003 Aug 27
Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi.
2003 Dec
Effect of the volatile constituents isolated from Thymus albicans, Th. mastichina, Th. carnosus and Thymbra capitata in sunflower oil.
2003 Dec
Odor compound detection in male euglossine bees.
2003 Jan
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 Jan
Erythema multiforme due to contact with weeds: a recurrence after patch testing.
2003 Jan
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
2003 Jun
Synergistic and antagonistic interactions of anticholinesterase terpenoids in Salvia lavandulaefolia essential oil.
2003 Jun
Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.
2003 Mar 12
Volatile metabolites from Salvia fruticosa as antifungal agents in soilborne pathogens.
2003 May 21
Composition and antimicrobial activity of Achillea clavennae L. essential oil.
2003 Nov
Seasonal and phenological variations of the essential oil from the narrow endemic species Artemisia molinieri and its biological activities.
2003 Nov 19
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
Osmitopsis asteriscoides (Asteraceae)-the antimicrobial activity and essential oil composition of a Cape-Dutch remedy.
2003 Oct
Effect of nitrogen concentration of the nutrient solution on the volatile constituents of leaves of Salvia fruticosa Mill. in solution culture.
2003 Oct 22
Essential oils from Mediterranean lamiaceae as weed germination inhibitors.
2003 Oct 8
Alternative termination chemistries utilized by monoterpene cyclases: chimeric analysis of bornyl diphosphate, 1,8-cineole, and sabinene synthases.
2003 Sep 15
Chemical composition and biological activity of Nepeta parnassica oils and isolated nepetalactones.
2003 Sep-Oct
Constraint of feeding by chronic ingestion of 1,8-cineole in the brushtail possum (Trichosurus vulpecula).
2004 Apr
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004 Feb
Chemical and biological evaluation of the essential oils of different Melaleuca species.
2004 Jan
Antifungal activity of Thymus oils and their major compounds.
2004 Jan
Transformation of terpenes using a Picea abies suspension culture.
2004 Jan 22
Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry.
2004 Jan 23
Antinociceptive profile of 2-phenylselenenyl-1,8-cineole in mice.
2004 Jun
Chemical composition of the essential oils of two Alpinia species from Hainan Island, China.
2004 Mar-Apr
Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions.
2004 May 5
Flavor release and perception in hard candy: influence of flavor compound-compound interactions.
2004 May 5
Ovicidal and adulticidal activity of Eucalyptus globulus leaf oil terpenoids against Pediculus humanus capitis (Anoplura: Pediculidae).
2004 May 5
Patents

Sample Use Guides

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
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.
Name Type Language
EUCALYPTOL
FCC   FHFI   HPUS   HSDB   II   INCI   MI   USAN   USP   USP-RS   VANDF  
USAN   INCI  
Official Name English
1,8-CINEOL
Common Name English
EUCALYPTOL [II]
Common Name English
CINEOLE
EP   INCI   MART.   WHO-DD  
INCI  
Official Name English
CINEOLE [MART.]
Common Name English
1,8-CINEOLE
Common Name English
EUCALYPTOL [MI]
Common Name English
1,8-EPOXY-P-MENTHANE
Systematic Name English
EUCALYPTOLE
Common Name English
CINEOLE [INCI]
Common Name English
NSC-6171
Code English
EUCALYPTOL [USP IMPURITY]
Common Name English
TERPAN
Common Name English
CAJEPUTOL
Common Name English
EUCALYPTOL [HPUS]
Common Name English
EUCALYPTOL [USP MONOGRAPH]
Common Name English
EUCALY
Common Name English
EUCALYPTOL [INCI]
Common Name English
Cineole [WHO-DD]
Common Name English
P-MENTHANE, 1,8-EPOXY-
Systematic Name English
EUCALYPTOL [USAN]
Common Name English
EUKALYPTOL
Common Name English
EUCALYPTOL [USP-RS]
Common Name English
2-OXA-1,3,3-TRIMETHYLBICYCLO(2.2.2)OCTANE
Systematic Name English
CINEOLE [EP MONOGRAPH]
Common Name English
EUCALYPTOL [VANDF]
Common Name English
EUCALYPTOL [FHFI]
Common Name English
P-CINEOLE
Common Name English
EUCALYPTOL [FCC]
Common Name English
1,3,3-TRIMETHYL-2-OXABICYCLO(2.2.2)OCTANE
Systematic Name English
FEMA NO. 2465
Code English
2-OXABICYCLO(2.2.2)OCTANE, 1,3,3-TRIMETHYL-
Systematic Name English
EUCAPUR
Common Name English
EUCALYPTOL [HSDB]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 172.515
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
WHO-VATC QR05CA13
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
JECFA EVALUATION EUCALYPTOL
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
NCI_THESAURUS C74536
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
WHO-ATC R05CA13
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
Code System Code Type Description
WIKIPEDIA
EUCALYPTOL
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
DAILYMED
RV6J6604TK
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
MERCK INDEX
M5208
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1268900
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
EPA CompTox
DTXSID4020616
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
CAS
470-82-6
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
ECHA (EC/EINECS)
207-431-5
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
RXCUI
21116
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY RxNorm
CHEBI
27961
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
DRUG CENTRAL
4259
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
HSDB
991
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
NSC
6171
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
PUBCHEM
2758
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
ChEMBL
CHEMBL485259
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
NCI_THESAURUS
C76772
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
FDA UNII
RV6J6604TK
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
SMS_ID
100000092061
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
EVMPD
SUB20486
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
MESH
C010087
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY
DRUG BANK
DB03852
Created by admin on Wed Jul 05 23:23:02 UTC 2023 , Edited by admin on Wed Jul 05 23:23:02 UTC 2023
PRIMARY