Identification

Namelimonene oxide
IUPAC6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
CAS Number1195-92-2
EINECS214-805-1
FDA UNIISearch
Molecular FormulaC10 H16 O
Molecular Weight152.23672000
MDL NumberMFCD00074770
Nikkaji NumberJ27.205A
Beilstein111814

Regulatory

JECFA Food Flavoring2145 D-8-p-menthene-1,2-epoxide
FEMA Number4655
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)203719-54-4 ; D-8-P-MENTHENE-1,2-EPOXIDE

Physical Properties

Appearance colorless to pale yellow clear liquid (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Specific Gravity 0.92600 to 0.93600 @ 20.00 °C.
Pounds per Gallon - (est). 7.714 to 7.798
Refractive Index 1.46400 to 1.47400 @ 20.00 °C.
Boiling Point 198.00 °C. @ 760.00 mm Hg (est)
Vapor Pressure 0.515000 mmHg @ 25.00 °C. (est)
Flash Point 150.00 °F. TCC ( 65.60 °C. ) (est)
logP (o/w) 3.200 (est)
Soluble in alcohol
Insoluble in water

Organoleptic Properties

Odor Description 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.

Safety Information

Oral/Parenteral Toxicityintramuscular-mouse LD50 100 mg/kg
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavor and fragrance agents
RIFM Fragrance Material Safety AssessmentSearch
baked goods-
beverages(nonalcoholic)0.05000
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes0.50000
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 products0.05000
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-

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Robinson Brothers Limited

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R C Treatt and Co Ltd

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Potential Uses

None Found

Natural Occurrence

orange fruit pepper japanese pepper spearmint oil

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