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General Material Information

Preferred name 1,8-cineole
Trivial Name 1,8-Cineole
Short Description eucalyptol
Formula C10 H18 O
CAS Number 470-82-6
FEMA Number 2465
Flavis Number 3.001
ECHA Number 207-431-5
FDA UNII RV6J6604TK
Nikkaji Number J3.281F
Beilstein Number 0105109
MDL MFCD00167977
COE Number 182
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1234 eucalyptol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 470-82-6 ; EUCALYPTOL
Synonyms
  • 2-oxa bicyclo(2.2.2)octane, 1,3,3-trimethyl-
  • 2-oxa bicyclo[2.2.2]octane, 1,3,3-trimethyl-
  • cajeputol
  • 1,8-cineole
  • p- cineole
  • 1,8-cineole natural
  • 1,8-epoxy-p-menthane
  • 1,8-epoxy-para-menthane
  • eucallyptol natural
  • eucalyptol
  • eucalyptol (ex eucalyptus globulus)
  • eucalyptol BP
  • eucalyptol codex naturel
  • eucalyptol FCC
  • eucalyptol FCC (natural)
  • eucalyptol natural
  • eucalyptol natural isolate
  • eucalyptol USP
  • eucalyptol USP natural
  • eucalyptol USP/FCC
  • 2-oxa-1,3,3-trimethyl bicyclo(2.2.2)octane
  • 1,3,3-trimethyl oxabicyclo(2.2.2)octane
  • 1,3,3-trimethyl-2-oxabicyclo(2.2.2)octane
  • 1,3,3-trimethyl-2-oxabicyclo[2,2,2]octane
  • 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane
  • 4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
  • 2-oxa-1,3,3-trimethylbicyclo(2.2.2)octane
  • 2-oxa-1,3,3-trimethylbicyclo[2.2.2]octane
  • 1,3,3-trimethyloxabicyclo(2.2.2)octane
  • 4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
  • 2-Oxabicyclo[2.2.2]octane, 1,3,3-trimethyl-
  • p-Menthane, 1,8-epoxy-
  • 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane
  • Cineol
  • Cineole
  • 1,8-Epoxy-p-menthane
  • Eucalyptole
  • 1,8-Cineol
  • p-Cineole
  • 2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane
  • Eucapur
  • Terpan
  • NSC 6171
  • Eukalyptol
  • Eucalytol
  • Eucaliptol
  • 1,8-Eucalyptol
  • FF 0964

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:470-82-6
Pubchem (cid):2758
Pubchem (sid):134975327
Flavornet:470-82-6
Pherobase:View
Publications by Info
1,8-CINEOLE
Publications by PubMed
Biological activities and chemical composition of the stems and roots of Helichrysum oligocephalum DC grown in Iran.
Chemical composition, antifungal and insecticidal activities of hedychium essential oils.
Comparison between Supercritical CO2 Extraction and Hydrodistillation for Two Species of Eucalyptus: Yield, Chemical Composition, and Antioxidant Activity.
Distillation time effect on lavender essential oil yield and composition.
Seasonal variations in the composition of the essential oils of rosemary (Rosmarinus officinalis, Lamiaceae).
Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone.
Bioactivities of volatile components from Nepalese Artemisia species.
Chemical variability of Algerian Myrtus communis L.
Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
Aroma characterization of tangerine hybrids by gas-chromatography-olfactometry and sensory evaluation.
Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species.
Antioxidant properties of Thymus vulgaris oil against aflatoxin-induce oxidative stress in male rats.
Comparative analysis of essential oils from eight herbal medicines with pungent flavor and cool nature by GC-MS and chemometric resolution methods.
Character impact odorants of fennel fruits and fennel tea.
Anticariogenic activity of macelignan isolated from Myristica fragrans (nutmeg) against Streptococcus mutans.
Effect of different locations on the chemical composition of essential oils of laurel (Laurus nobilis L.) leaves growing wild in Turkey.
Glycosidically bound volatiles and flavor precursors in Laurus nobilis L.
Flavor release and perception in hard candy: influence of flavor compound-flavor solvent interactions.
Flavor release and perception in hard candy: influence of flavor compound-compound interactions.
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
Aroma content of fresh basil (Ocimum basilicum L.) leaves is affected by light reflected from colored mulches.
Influence of drying on the flavor quality of spearmint (Mentha spicata L.).
Variation in odor thresholds for l-carvone and cineole and correlations with suprathreshold intensity ratings.
Essential oil from Artemisia phaeolepis: chemical composition and antimicrobial activities.
Roles of the volatile terpene, 1,8-cineole, in plant-herbivore interactions: a foraging odor cue as well as a toxin?
Odor qualities and thresholds of physiological metabolites of 1,8-cineole as an example for structure-activity relationships considering chirality aspects.
Aroma chemistry of African Oryza glaberrima and Oryza sativa rice and their interspecific hybrids.
Olfactory training in patients with Parkinson's disease.
Response times and response accuracy for odor localization and identification.
Dual processing streams in chemosensory perception.
Comparison of odor-active compounds in grapes and wines from vitis vinifera and non-foxy American grape species.
Hemisynthesis of dihydroumbellulols from umbellulone: new cooling compounds.
Localisation of unilateral nasal stimuli across sensory systems.
Volatiles released from Vaccinium corymbosum were attractive to Aegorhinus superciliosus (Coleoptera: Curculionidae) in an olfactometric bioassay.
Effects of olfactory training in patients with olfactory loss.
Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
Manuka oil and phoebe oil are attractive baits for Xyleborus glabratus (Coleoptera: Scolytinae), the vector of laurel wilt.
Odor localization and sniffing.
Aroma constituents and alkylamides of red and green huajiao (Zanthoxylum bungeanum and Zanthoxylum schinifolium).
Character impact odorants of fennel fruits and fennel tea.
Volatile constituents and key odorants in leaves, buds, flowers, and fruits of Laurus nobilis L.
Analysis of the essential oils of the leaves, stems, rhizomes and roots of the medicinal plant Alpinia galanga from southern India.
Fragrance chemistry, nocturnal rhythms and pollination "syndromes" in Nicotiana.
Effects of olfactory function, age, and gender on trigeminally mediated sensations: a study based on the lateralization of chemosensory stimuli.
Influence of drying on the flavor quality of spearmint (Mentha spicata L.).
Mitral cell temporal response patterns evoked by odor mixtures in the rat olfactory bulb.
Improved hardware and software for quick gas chromatography-olfactometry using CHARM and GC-"SNIF" analysis.
Antimicrobial and bactericidal activities of esters of 2-endo-hydroxy-1,8-cineole as new aroma chemicals.
Central role of the CNGA4 channel subunit in Ca2+-calmodulin-dependent odor adaptation.
Optical recording of odor-evoked responses in the olfactory brain of the naïve and aversively trained terrestrial snails.
Orbital cortex neuronal responses during an odor-based conditioned associative task in rats.
Amplification of odor-induced Ca(2+) transients by store-operated Ca(2+) release and its role in olfactory signal transduction.
Sensory properties of selected terpenes. Thresholds for odor, nasal pungency, nasal localization, and eye irritation.
Na+-dependent Ca2+ extrusion governs response recovery in frog olfactory receptor cells.
Fast wave activity in the rat rhinencephalon: elicitation by the odors of phytochemicals, organic solvents, and a rodent predator.
Trigeminal perception of odorant quality in congenitally anosmic subjects.
Identification of a long-lasting form of odor adaptation that depends on the carbon Monoxide/cGMP second-messenger system.
Effects of altered olfactory experiences on the development of infant rats' responses to odors.
Variation in odor thresholds for l-carvone and cineole and correlations with suprathreshold intensity ratings.
Effects of odorants on pigment aggregation and cAMP in fish melanophores.
Discriminating parts from the whole: determinants of odor mixture perception in squirrel monkeys, Saimiri sciureus.
A four-component attractant for the mexican fruit fly,Anastrepha ludens (Diptera: Tephritidae), from host fruit.
Evaluation of antifungal volatile compounds on the basis of the elongation rate of a single hypha.
Olfactory bulb size, odor discrimination and magnetic insensitivity in hummingbirds.
Olfactory responses of a specialist and a generalist grasshopper to volatiles ofArtemisia ludoviciana nutt. (Asteraceae).
Intracellular potentials of salamander mitral/tufted neurons in response to odor stimulation.
Some effects of conditioned aversion on food intake and olfactory bulb electrical responses in the rat.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Metabolomics Database:Search
KEGG (GenomeNet):C09844
HMDB (The Human Metabolome Database):HMDB04472
FooDB:FDB014616
Export Tariff Code:2909.20.00
MedlinePlusSupp:View
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Formulations/Preparations:
•grades: technical; nf. •technical grade purity of 99.6-99.8% •eucalyptus oil is about 70% active eucalyptol.

Suppliers

Alfa Biotechnology Anhui Haibei
Arora Aromatics Augustus Oils
Aurochemicals Berjé
Bontoux Charabot
Charkit Chemical Chemia
Citrus and Allied Essences De Monchy Aromatics
Diffusions Aromatiques ECSA Chemicals
Ernesto Ventós Excellentia International
ExtraSynthese Fleurchem
Foreverest Resources Frey + Lau
Fuzhou Farwell Glentham Life Sciences
Global Essence H. Interdonati, Inc.
Indenta Group Indukern F&F
Jiangyin Healthway John Kellys (London)
K.L. Koh Enterprise Keva
Lluch Essence M&U International
Mane Mentha & Allied Products
Moellhausen Nectar Lifesciences
Nippon Terpene Chemicals OQEMA
Pearlchem Corporation Pell Wall Perfumes
Penta International PerfumersWorld
Perfumery Laboratory Phoenix Aromas & Essential Oils
Prodasynth Quimdis
R C Treatt & Co Ltd Reincke & Fichtner
Robertet Sachee
Sensient Flavor and Fragrances Sigma-Aldrich
Silver Fern Chemical SRS Aromatics
Sunaux International Symrise
Synerzine TCI AMERICA
Tengzhou Xiang Yuan Aroma Chemicals The John D. Walsh Company
The Lermond Company The Perfumers Apprentice
Ungerer & Company Vigon International
Xiamen Doingcom Chemical Augustus Oils Ltd
Berje Inc. Bontoux SAS
Charkit Chemical Corporation Fleurchem, Inc.
Foreverest Resources Ltd. Glentham Life Sciences Ltd
Global Essence Inc. Indukern, S.A. F&F Ingredients Division
Jiangyin Healthway International Trade Co., Ltd Lluch Essence S.L.
M&U International LLC Moellhausen S.P.A.
Penta International Corporation PerfumersWorld Ltd.
Robertet, Inc. SRS Aromatics Ltd
Symrise AG Synerzine, Inc.
The John D. Walsh Company, Inc R C Treatt and Co Ltd
Ernesto Ventós S.A.

PhysChem Properties

Material listed in food chemical codex Yes
Molecular weight 154.2526550293
Specific gravity @ 25 °C
Pounds per Gallon 7.647 to 7.664
Refractive Index 1.448 to 1.451 @ 20 °C
Melting Point 1 to 2°C @ 760 mm Hg
Boiling Point 176 to 177°C @ 760 mm Hg
Boiling Point 90 to 91°C @ 760 mm Hg
Vapor Pressure 1.9 mmHg @ 25 °C
Flash Point TCC Value 50 °C TCC
logP (o/w) 2.74
Solubility
alcohol Yes
fixed oils Yes
water, 332.1 mg/L @ 25 °C (est) Yes
water, 3500 mg/L @ 21C (exp) Yes
Stability
bath foam Unspecified
cream Unspecified
lipstick Unspecified
lotion Unspecified
non-discoloring Unspecified
shampoo Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Herbal
eucalyptus, herbal, camphoreous, medicinal
Odor strength high , recommend smelling in a 10.00 % solution or less
Substantivity 4 hour(s) at 100.00 %
Luebke, William tgsc, (1995) At 10.00 % in dipropylene glycol. eucalyptus herbal camphor medicinal
Flavor Type: Minty
minty, camphoreous, cooling, eucalyptus, medicinal
Luebke, William tgsc, (1995) Minty camphoreous cooling eucalyptus medicinal
Useful in: mint, savory spices. Eucalyptus, minty, fresh, cooling, herbal
General comment Eucalyptol, balsamic

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 10 - Flammable.
R 36 - Irritating to eyes.
S 02 - Keep out of the reach of children.
S 16 - Keep away from sources of ignition - No Smoking.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Human Experience:
16 % solution: no irritation or sensitization.
Oral/Parenteral Toxicity:
oral-rat LD50 [sex: M,F] 2480 mg/kg
(Bär & Griepentrog, 1967)

oral-rat LD50 [sex: M,F] 2480 mg/kg
(Jenner et al., 1964)

oral-rat LD50 [sex: M,F] 1550 mg/kg
(Brownlee, 1940)

intramuscular-guinea pig LDLo 2250 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Trudy Instituta Fiziologii, Akademiya Nauk Kazakhshoi SSR. Transactions of the Institute of Physiology, Academy of Sciences of the Kazakh. SSR. Vol. 1, Pg. 134, 1955.

intramuscular-mouse LD50 1000 mg/kg
Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.

oral-rat LD50 2480 mg/kg
BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: COMA
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

subcutaneous-mouse LD50 1070 mg/kg
PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Sapporo Igaku Zasshi. Sapporo Medical Journal. Vol. 3, Pg. 73, 1952.

subcutaneous-dog LDLo 1500 mg/kg
SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Trudy Instituta Fiziologii, Akademiya Nauk Kazakhshoi SSR. Transactions of the Institute of Physiology, Academy of Sciences of the Kazakh. SSR. Vol. 1, Pg. 134, 1955.

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for 1,8-cineole usage levels up to:
20.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 1200.00 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 1954.00 (μg/capita/day)
Structure Class: II
Use levels for FEMA GRAS flavoring substances on which the FEMA Expert Panel based its judgments that the substances are generally recognized as safe (GRAS).
The Expert Panel also publishes separate extensive reviews of scientific information on all FEMA GRAS flavoring substances and can be found at FEMA Flavor Ingredient Library
publication number: 3
Click here to view publication 3
average usual ppmaverage maximum ppm
baked goods: 0.500004.00000
beverages(nonalcoholic): -0.13000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: -190.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -0.50000
fruit ices: -0.50000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: -15.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 23 (FGE.23): Aliphatic, alicyclic and aromatic ethers including anisole derivatives From chemical groups 15, 16 and 26 (Commission Regulation (EC) No 1565/2000 of 18 July 2000
View page or View pdf

Flavouring Group Evaluation 59 (FGE.59): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 (2006) (Commission Regulation (EC) No 1565/2000 of 18 July 2000) - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in contact with Food (AFC)
View page or View pdf

Flavouring Group Evaluation 23, Revision 1 (FGE.23Rev1): Aliphatic, alicyclic and aromatic ethers including anisole derivatives from chemical groups 15, 16, 26 and 30[1] - Opinion of the Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 33 (FGE.33)[1] - Six Tetrahydrofuran Derivatives from Chemical Groups 13, 14, 16 and 26 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 75 (FGE.75)[1] - Consideration of tetrahydrofuran derivatives and a furanone derivative evaluated by JECFA (63rd meeting) structurally related to tetrahydrofuran derivatives evaluated by EFSA in FGE.33 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 59, Revision 1 (FGE.59Rev1): Consideration of aliphatic and aromatic ethers evaluated by JECFA (61st meeting and 63rd meeting) structurally related to aliphatic, alicyclic and aromatic ethers including anisole derivatives evaluated by EFSA in FGE.23 Rev2 (2010)
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
Carcinogenic Potency Database:Search
EPA Substance Registry Services (TSCA):470-82-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :2758
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:2
4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane
Chemidplus:0000470826
EPA/NOAA CAMEO:hazardous materials
RTECS:OS9275000 for cas# 470-82-6