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limonene oxide

Chemical Structure

General Material Information

Preferred name limonene oxide
Trivial Name Limonene oxide
Short Description D-8-p-menthene-1,2-epoxide
Formula C10 H16 O
CAS Number 1195-92-2
Deleted CAS Number 10008-60-3
FEMA Number 4655
ECHA Number 214-805-1
FDA UNII Search
Nikkaji Number J27.205A
Beilstein Number 111814
MDL MFCD00074770
xLogP3-AA 2.50 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 2145 D-8-p-menthene-1,2-epoxide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 203719-54-4 ; D-8-P-MENTHENE-1,2-EPOXIDE
Synonyms
  • 7-oxa bicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-
  • 7-oxa bicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-
  • 1,2-epoxylimonene
  • limonene 1,2-epoxide
  • limonene 1,2-oxide
  • limonene epoxide
  • (cis+trans)-1,2-(+)- limonene oxide
  • limonene oxide mixed isomers
  • (+)- limonene oxide, mixture of cis and trans
  • D-8-p- menthene-1,2-epoxide
  • 6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
  • 1-methyl-4-(1-methylethenyl)-7-oxabicyclo(4.1.0)heptane
  • 1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane
  • 1-methyl-4-(1-methylvinyl)-7-oxabicyclo(4.1.0)heptane
  • 1-methyl-4-(1-methylvinyl)-7-oxabicyclo[4.1.0]heptane
  • 1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane
  • 4-iso propenyl-1-methyl-7-oxabicyclo[4.1.0]heptan
  • 4-iso propenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
  • 6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
  • 7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-
  • p-Menth-8-ene, 1,2-epoxy-
  • 1-Methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptane
  • 1,2-Epoxy-p-menth-8-ene
  • Limonene monoxide
  • 1,2-Epoxylimonene
  • LMO
  • NSC 12045
  • Cis/trans-(S)-(-)-limonene oxide
  • 1-Methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptane

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

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Literature & References

6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1195-92-2
Pubchem (cid):91496
Pubchem (sid):135049028
Pherobase:View
Publications by Google Patents
Pyrolysis of limonene oxide
Publications by PubMed
Photocatalysis of sub-ppm limonene over multiwalled carbon nanotubes/titania composite nanofiber under visible-light irradiation.
Synthesis and structural revision of a brominated sesquiterpenoid, aldingenin C.
Structural characterization of a hypothetical protein: a potential agent involved in trimethylamine metabolism in Catenulispora acidiphila.
Potential antioxidant and anxiolytic effects of (+)-limonene epoxide in mice after marble-burying test.
Computationally designed libraries for rapid enzyme stabilization.
Study of ozone-initiated limonene reaction products by low temperature plasma ionization mass spectrometry.
Anthelmintic activity of the natural compound (+)-limonene epoxide against Schistosoma mansoni.
Olfactory discrimination ability of South African fur seals (Arctocephalus pusillus) for enantiomers.
Evaluation of acute toxicity of a natural compound (+)-limonene epoxide and its anxiolytic-like action.
Indoloquinazoline alkaloids from Euodia rutaecarpa and their cytotoxic activities.
QM/MM study of the mechanism of enzymatic limonene 1,2-epoxide hydrolysis.
Total synthesis of (+)-cymbodiacetal: a re-evaluation of the biomimetic route.
Evaluation of allergenicity of constituents of myoga using the murine local lymph node assay.
Thorough evaluation of the validity of conventional enantio-gas chromatography in the analysis of volatile chiral compounds in mandarin essential oil: A comparative investigation with multidimensional gas chromatography.
Conformational preference of a chiral terpene: vibrational circular dichroism (VCD), infrared and Raman study of S-(-)-limonene oxide.
Structure and spasmolytic activity relationships of monoterpene analogues found in many aromatic plants.
Effect of needle damage on the release rate of Masson pine (Pinus massoniana) volatiles.
Acaricidal activity of limonene, limonene oxide and beta-amino alcohol derivatives on Rhipicephalus (Boophilus) microplus.
Chemical and physical stability of protein and gum arabic-stabilized oil-in-water emulsions containing limonene.
Screening of antibacterial activities of twenty-one oxygenated monoterpenes.
Heterogeneous reactions of ozone and D-limonene on activated carbon.
Antinociceptive activity of structural analogues of rotundifolone: structure-activity relationship.
Chemical and physical stability of citral and limonene in sodium dodecyl sulfate-chitosan and gum arabic-stabilized oil-in-water emulsions.
Toxicity study of the volatile constituents of Myoga utilizing acute dermal irritation assays and the Guinea-pig Maximization test.
Evaluation of characteristic aroma compounds of Citrus natsudaidai Hayata (Natsudaidai) cold-pressed peel oil.
Evidence for the role of the monB genes in polyether ring formation during monensin biosynthesis.
Stereoselective biotransformation of limonene and limonene oxide by cyanobacterium, Synechococcus sp. PCC 7942.
Catalytic mechanism of limonene epoxide hydrolase, a theoretical study.
Structure of an atypical epoxide hydrolase from Mycobacterium tuberculosis gives insights into its function.
[Terpenoids in root exudates of different allelopathic rice varieties].
Integron-associated mobile gene cassettes code for folded proteins: the structure of Bal32a, a new member of the adaptable alpha+beta barrel family.
The number of functional olfactory receptor genes and the relative size of olfactory brain structures are poor predictors of olfactory discrimination performance with enantiomers.
Alternating copolymerization of limonene oxide and carbon dioxide.
Olfactory discrimination ability of human subjects for enantiomers with an isopropenyl group at the chiral center.
Transformation of terpenes using a Picea abies suspension culture.
Patch testing with oxidized R-(+)-limonene and its hydroperoxide fraction.
Structure of Rhodococcus erythropolis limonene-1,2-epoxide hydrolase reveals a novel active site.
Determination of limonene oxidation products using SPME and GC-MS.
Oxide terpenes as human skin penetration enhancers of haloperidol from ethanol and propylene glycol and their modes of action on stratum corneum.
Effects of storage conditions on the composition of Citrus tamurana Hort. ex Tanaka (hyuganatsu) essential oil.
Additive toxicity of limonene and 50% oxygen and the role of glutathione in detoxification in human lung cells.
Characterization of tert-butyl alcohol binding to alpha2u-globulin in F-344 rats.
Biotransformation of (R)-(+)- and (S)-(-)-limonene by fungi and the use of solid phase microextraction for screening.
Aroma-active compounds of miniature beefsteakplant (Mosla dianthera Maxim).
Evaluation of the in vivo interaction of methyl tert-butyl ether with alpha2u-globulin in male F-344 rats.
Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene.
The structures of alpha 2u-globulin and its complex with a hyaline droplet inducer.
The Rhodococcus erythropolis DCL14 limonene-1,2-epoxide hydrolase gene encodes an enzyme belonging to a novel class of epoxide hydrolases.
Limonene-1,2-epoxide hydrolase from Rhodococcus erythropolis DCL14 belongs to a novel class of epoxide hydrolases.
2-sec-butyl-4,5-dihydrothiazole is a ligand for mouse urinary protein and rat alpha 2u-globulin: physiological and toxicological relevance.
Effect of selected monoterpenes on methane oxidation, denitrification, and aerobic metabolism by bacteria in pure culture.
In vitro uptake of methyl tert-butyl ether in male rat kidney: use of a two-compartment model to describe protein interactions.
Electroantennogram activity from antennae ofCeratitis capitata (Wied.) to fresh orange airborne volatiles.
Inhibition of tumor cell growth by monoterpenes in vitro: evidence of a Ras-independent mechanism of action.
Alpha 2u-globulin is the only member of the lipocalin protein superfamily that binds to hyaline droplet inducing agents.
Air oxidation of d-limonene (the citrus solvent) creates potent allergens.
Biochemical basis for mouse resistance to hyaline droplet nephropathy: lack of relevance of the alpha 2u-globulin protein superfamily in this male rat-specific syndrome.
Animal experiments on the allergenicity of d-limonene--the citrus solvent.
Design of a gas chromatograph with parallel radioactivity and mass spectrometric detection. Application to the identification of the major metabolite of d-limonene associated with alpha 2u-globulin.
Characteristics of chemical binding to alpha 2u-globulin in vitro--evaluating structure-activity relationships.
Lysosomal degradation of alpha 2u-globulin and alpha 2u-globulin-xenobiotic conjugates.
Metabolism of limonene-1,2-epoxide 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
CHEBI:View
CHEMBL:View
UM BBD:Search
KEGG (GenomeNet):C07271
HMDB (The Human Metabolome Database):HMDB35158
FooDB:FDB013795
Export Tariff Code:2932.99.0090
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Specific gravity @ 20 °C
Pounds per Gallon 7.714 to 7.798
Refractive Index 1.464 to 1.474 @ 20 °C
Vapor Pressure 0.515 mmHg @ 25 °C
Flash Point TCC Value 65.6 °C TCC
logP (o/w) 3.2 est
Solubility
alcohol Yes
water, 137.2 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Citrus
fresh, clean, citrus, minty, spearmint, herbal
General comment Used in citrus and minty flavours: at 0.3-0.5ppm in beverages and dairy products, and up to 5ppm in sauces.Note: the epoxide can be lost in alcoholic and aqueous solutions, in acidic conditions. fresh clean citrus minty spearmint herbal

Occurrences

Safety Information

Safety information

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:
intramuscular-mouse LD50 100 mg/kg
Journal of Scientific and Industrial Research, Section C: Biological Sciences. Vol. 21, Pg. 342, 1962.

oral-mouse LD50 2700 uL/kg
Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 9, Pg. 518, 1978.

Dermal Toxicity:
Not determined
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
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: 24
Click here to view publication 24
average usual ppmaverage maximum ppm
baked goods: --
beverages(nonalcoholic): 0.050000.50000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: 0.500005.00000
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: --
imitation dairy: --
instant coffee / tea: --
jams / jellies: --
meat products: --
milk products: 0.050000.50000
nut products: --
other grains: --
poultry: --
processed fruits: --
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: --
snack foods: --
soft candy: --
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

EPI System: View
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1195-92-2
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91496
National Institute of Allergy and Infectious Diseases:Data
6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
Chemidplus:0001195922