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

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

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
The water-soluble components of the essential oil of Melaleuca alternifolia (tea tree oil) suppress the production of superoxide by human monocytes, but not neutrophils, activated in vitro.
2001 Apr
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
Volatile essential oil constituents of Alpinia smithiae (Zingiberaceae).
2001 Jun
Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens.
2001 Mar
Essential oils from Azorean Laurus azorica.
2001 May
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
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
Monoterpenoid accumulation in Melaleuca alternifolia seedlings.
2002 Apr
Inhibition of the microsomal metabolism of 1,8-cineole in the common brushtail possum (Trichosurus vulpecula) by terpenes and other chemicals.
2002 Dec
Cardiovascular effects of 1,8-cineole, a terpenoid oxide present in many plant essential oils, in normotensive rats.
2002 Dec
Antipredator defense of biological control agent Oxyops vitiosa is mediated by plant volatiles sequestered from the host plant Melaleuca quinquenervia.
2002 Feb
Main agronomic-productive characteristics of two ecotypes of Rosmarinus officinalis L. and chemical composition of their essential oils.
2002 Jun 5
Chemical composition and in-vitro antimicrobial activity of the essential oils of three Greek Achillea species.
2002 Mar-Apr
Insecticidal properties of essential plant oils against the mosquito Culex pipiens molestus (Diptera: Culicidae).
2002 May
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
Near infrared spectroscopy for cost effective screening of foliar oil characteristics in a Melaleuca cajuputi breeding population.
2003 Apr 23
Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches.
2003 Apr 9
Essential oils produced by in vitro shoots of sage (Salvia officinalis L.).
2003 Apr 9
Chemical composition and antibacterial activity of essential oil of Artemisia iwayomogi.
2003 Dec
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
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
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
Analysis of volatile components of Lavandula luisieri L. by direct thermal desorption-gas chromatography-mass spectrometry.
2004 Jan 23
Flavor release and perception in hard candy: influence of flavor compound-flavor solvent 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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:35 GMT 2023
Edited
by admin
on Fri Dec 15 15:54:35 GMT 2023
Record UNII
RV6J6604TK
Record Status Validated (UNII)
Record Version
  • Download
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 Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
WHO-VATC QR05CA13
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
JECFA EVALUATION EUCALYPTOL
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
NCI_THESAURUS C74536
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
WHO-ATC R05CA13
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
Code System Code Type Description
WIKIPEDIA
EUCALYPTOL
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
DAILYMED
RV6J6604TK
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
MERCK INDEX
m5208
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PRIMARY Merck Index
RS_ITEM_NUM
1268900
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PRIMARY
EPA CompTox
DTXSID4020616
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PRIMARY
CAS
470-82-6
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PRIMARY
ECHA (EC/EINECS)
207-431-5
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
RXCUI
21116
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY RxNorm
CHEBI
27961
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PRIMARY
DRUG CENTRAL
4259
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
HSDB
991
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
NSC
6171
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
PUBCHEM
2758
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
ChEMBL
CHEMBL485259
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
NCI_THESAURUS
C76772
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
FDA UNII
RV6J6604TK
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
SMS_ID
100000092061
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
EVMPD
SUB20486
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
MESH
C010087
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
JECFA MONOGRAPH
1243
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
DRUG BANK
DB03852
Created by admin on Fri Dec 15 15:54:35 GMT 2023 , Edited by admin on Fri Dec 15 15:54:35 GMT 2023
PRIMARY
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