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1,4-cineole

Chemical Structure

General Material Information

Preferred name 1,4-cineole
Trivial Name 1,4-Cineole
Short Description 4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane
Formula C10 H18 O
CAS Number 470-67-7
Deleted CAS Number 21499-90-1
FEMA Number 3658
Flavis Number 3.007
ECHA Number 207-428-9
FDA UNII B55JTU839B
Nikkaji Number J5.939K
Beilstein Number 0104974
MDL MFCD00209502
COE Number 11225
xLogP3-AA 2.50 (est)
NMR Predictor External link
JECFA Food Flavoring 1233 1,4-cineole
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 470-67-7 ; 1,4-CINEOLE
Synonyms
  • 7-oxa bicyclo(2.2.1)heptane, 1-isopropyl-4-methyl-
  • 7-oxa bicyclo(2.2.1)heptane, 1-methyl-4-(1-methylethyl)-
  • 7-oxa bicyclo[2.2.1]heptane, 1-methyl-4-(1-methylethyl)-
  • 1,4-cineole
  • iso cineole
  • 1,4-cineole (natural)
  • 1,4-cineole natural
  • 1,4-cineole synthetic
  • 1,4-epoxy-p-menthane
  • 1,4-epoxy-para-menthane
  • iso eucalyptol
  • p- menthane, 1,4-epoxy
  • 4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane
  • 1-methyl-4-(1-methyl ethyl)-7-oxabicyclo(2.2.1)heptane
  • 1-methyl-4-(1-methylethyl)-7-oxabicyclo(2.2.1)heptane
  • 1-methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane
  • 1-methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane
  • 1-iso propyl-4-methyl-7-oxabicyclo(2.2.1)heptane
  • 1-iso propyl-4-methyl-7-oxabicyclo[2.2.1]heptane
  • 4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane
  • 7-Oxabicyclo[2.2.1]heptane, 1-methyl-4-(1-methylethyl)-
  • p-Menthane, 1,4-epoxy-
  • 7-Oxabicyclo[2.2.1]heptane, 1-isopropyl-4-methyl-
  • 1-Methyl-4-(1-methylethyl)-7-oxabicyclo[2.2.1]heptane
  • Isocineole
  • 1,4-Cineol
  • 1-Methyl-4-(propan-2-yl)-7-oxabicyclo[2.2.1]heptane

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

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Literature & References

4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:470-67-7
Pubchem (cid):10106
Pubchem (sid):134975326
Flavornet:470-67-7
Pherobase:View
Publications by PubMed
Nematicidal activity of the essential oil of Rhododendron anthopogonoides aerial parts and its constituent compounds against Meloidogyne incognita.
Inhibition by menthol and its related chemicals of compound action potentials in frog sciatic nerves.
1,8-cineole, a TRPM8 agonist, is a novel natural antagonist of human TRPA1.
Toxicity of Rhododendron anthopogonoides essential oil and its constituent compounds towards Sitophilus zeamais.
Interactions between novel terpenes and main components of rat and human skin: mechanistic view for transdermal delivery of propranolol hydrochloride.
Herbicidal activity of cineole derivatives.
[Analysis of the chemical constituents of essential oil from Chimonanthus zhejiangensis by GC-MS].
Anxiolytic-like effect of the monoterpene 1,4-cineole in mice.
Roles of cytochrome P450 3A enzymes in the 2-hydroxylation of 1,4-cineole, a monoterpene cyclic ether, by rat and human liver microsomes.
Inhibition of plant asparagine synthetase by monoterpene cineoles.
[GC-MS analysis of constituents of essential oils from stems of Ephedra sinica Stapf, E. intermedia Schrenk et C.A. Mey. and E. equisetina Bge].
A soluble Bacillus cereus cytochrome P-450cin system catalyzes 1,4-cineole hydroxylations.
Biotransformation of 1,4-cineole, a monoterpene ether.
Microbial hydroxylation of 1,4-cineole.
Effect of odor quality and intensity on conditioned odor aversion learning 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
KEGG (GenomeNet):C16909
HMDB (The Human Metabolome Database):HMDB36096
FooDB:FDB014936
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 154.2526550293
Specific gravity @ 25 °C
Pounds per Gallon
Boiling Point 172 to 174°C @ 760 mm Hg
Vapor Pressure 1.93 mmHg @ 25 °C
Flash Point TCC Value 47.78 °C TCC
logP (o/w) 2.97
Solubility
alcohol Yes
water, 211.3 mg/L @ 25 °C (est) Yes

Organoleptic Properties

Odor Type: Herbal
cooling, pine, minty, camphoreous, terpenic, green, eucalyptus
Odor strength high , recommend smelling in a 10.00 % solution or less
Substantivity 4 hour(s) at 100.00 %
General comment At 10.00 % in dipropylene glycol. cooling pine minty camphor terpene green
Mosciano, Gerard P&F 17, No. 3, 57, (1992) Minty, cooling piney, camphoraceous, eucalyptol-like
Flavor Type: Cooling
cooling, minty, mentholic, green, herbal, terpenic, camphoreous
Mosciano, Gerard P&F 17, No. 3, 57, (1992) At 40.00 ppm. Cooling, minty, menthol-like, green and herbal, with a terpy and camphoraceous nuance

Occurrences

Potential Uses

Applications
Odor purposes Citrus, Eucalyptus oil replacer, Lime, Mint, Spice
Flavoring purposes Fruit tropical fruit
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
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.
Oral/Parenteral Toxicity:
oral-rat LD50 3100 mg/kg
(Moreno, 1981c)

oral-rat LD50 > 5000 mg/kg
(Moreno, 1972d)

oral-rat LD50 3100 mg/kg
Food and Chemical Toxicology. Vol. 26, Pg. 291, 1988.

Dermal Toxicity:
skin-rabbit LD50 > 5000 mg/kg
Food and Chemical Toxicology. Vol. 26, Pg. 291, 1988.

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 1,4-cineole usage levels up to:
40.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 3.90 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 146.00 (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: 13
Click here to view publication 13
average usual ppmaverage maximum ppm
baked goods: -12.40000
beverages(nonalcoholic): -9.21000
beverages(alcoholic): -4.71000
breakfast cereal: --
cheese: --
chewing gum: -25.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -9.62000
fruit ices: --
gelatins / puddings: -9.91000
granulated sugar: --
gravies: --
hard candy: -50.00000
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: -8.29000
milk products: --
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: -11.49000
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

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
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):470-67-7
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :10106
National Institute of Allergy and Infectious Diseases:Data
WISER:UN 1993
WGK Germany:2
4-methyl-1-propan-2-yl-7-oxabicyclo[2.2.1]heptane
Chemidplus:0000470677
RTECS:OS9274000 for cas# 470-67-7