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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H18O
Molecular Weight 154.2497
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EUCALYPTOL

SMILES

CC1(C)[C@@]2([H])CCC(C)(CC2)O1

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 154.2497
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 0 / 0
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
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
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
Differential metabolism of 1,8-cineole in insects.
2003 Jan
Erythema multiforme due to contact with weeds: a recurrence after patch testing.
2003 Jan
Noninvasive glucose monitoring by back diffusion via skin: chemical and physical enhancements.
2003 Jul
Preferred age for assessment of qualitative and quantitative characteristics of the essential oil of tea tree (Melaleuca alternifolia) seedlings prior to plantation establishment.
2003 Jul 16
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
Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana.
2003 Jun
Insecticidal activity and chemical composition of volatile oils from Hyptis martiusii Benth.
2003 Jun 18
Antibacterial activity and chemical composition of essential oil of Chrysanthemum boreale.
2003 Mar
Monoterpenoid accumulation in 1,8-cineole, terpinolene and terpinen-4-ol chemotypes of Melaleuca alternifolia seedlings.
2003 Mar
Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse.
2003 Mar 12
Antimicrobial and antioxidant activities of three Mentha species essential oils.
2003 May
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
Effects of a novel gaseous antioxidative system containing a rosemary extract on the oxidation induced by nitrogen dioxide and ultraviolet radiation.
2004 Apr
1,8-cineole (eucalyptol), a monoterpene oxide attenuates the colonic damage in rats on acute TNBS-colitis.
2004 Apr
Evaluation of toxic/protective effects of the essential oil of Salvia officinalis on freshly isolated rat hepatocytes.
2004 Aug
Characterization of the mouse cold-menthol receptor TRPM8 and vanilloid receptor type-1 VR1 using a fluorometric imaging plate reader (FLIPR) assay.
2004 Feb
Characteristics, clinical effect profile and tolerability of a nasal spray preparation of Artemisia abrotanum L. for allergic rhinitis.
2004 Jan
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
Effect of monoterpenes on lipid oxidation in maize.
2004 Jun
Comparative study of the essential oils and extracts of Achillea fragrantissima (Forssk.) Sch. Bip. and Achillea santolina L. (Asteraceae) from Egypt.
2004 Mar
Inhibition of acetylcholinesterase by Tea Tree oil.
2004 Mar
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
2004 Mar 24
Chemical composition of the essential oils of two Alpinia species from Hainan Island, China.
2004 Mar-Apr
Proton-transfer-reaction mass spectrometry as a new tool for real time analysis of root-secreted volatile organic compounds in Arabidopsis.
2004 May
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.
Substance Class Chemical
Created
by admin
on Fri Jun 25 20:58:58 UTC 2021
Edited
by admin
on Fri Jun 25 20:58:58 UTC 2021
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
CINEOLE [WHO-DD]
Common Name English
EUCALYPTOLE
Common Name English
CINEOLE [INCI]
Common Name English
NSC-6171
Code 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
P-MENTHANE, 1,8-EPOXY-
Systematic Name English
EUCALYPTOL [USAN]
Common Name English
EUKALYPTOL
Common Name English
EUCALYPTOL [USP-RS]
Common Name English
EUCALYPTOL [USP]
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 Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
WHO-VATC QR05CA13
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
JECFA EVALUATION EUCALYPTOL
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
NCI_THESAURUS C74536
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
WHO-ATC R05CA13
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
Code System Code Type Description
WIKIPEDIA
EUCALYPTOL
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
MERCK INDEX
M5208
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY Merck Index
EPA CompTox
470-82-6
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
CAS
470-82-6
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
ECHA (EC/EINECS)
207-431-5
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
RXCUI
21116
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
4259
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
HSDB
991
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
PUBCHEM
2758
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
ChEMBL
CHEMBL485259
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
NCI_THESAURUS
C76772
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
FDA UNII
RV6J6604TK
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
EVMPD
SUB20486
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
MESH
C010087
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
USP_CATALOG
1268900
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY USP-RS
DRUG BANK
DB03852
Created by admin on Fri Jun 25 20:58:58 UTC 2021 , Edited by admin on Fri Jun 25 20:58:58 UTC 2021
PRIMARY
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