EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

limonene oxide
D-8-p-menthene-1,2-epoxide

Sponsors

Name:6-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
CAS Number: 1195-92-2Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:214-805-1
Nikkaji Web:J27.205A
Beilstein Number:111814
MDL:MFCD00074770
XlogP3-AA:2.50 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome or firefox)
Category:flavor and fragrance agents
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Perfumer and Flavorist:Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
JECFA Food Flavoring:2145 D-8-p-menthene-1,2-epoxide
FEMA Number:4655 D-8-p-menthene-1,2-epoxide
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: 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 mm/Hg @ 25.00 °C. (est)
Flash Point: 150.00 °F. TCC ( 65.60 °C. ) (est)
logP (o/w): 3.200 (est)
Soluble in:
 alcohol
 water, 137.2 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: citrus
fresh clean citrus minty spearmint herbal
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.fresh clean citrus minty spearmint herbal
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Limonene-1,2-epoxide
Penta International
LIMONENE OXIDE MIXED ISOMERS, Kosher
Robinson Brothers
(+)-Limonene oxide, mixture of cis and trans F&F
https://www.robinsonbrothers.uk/chemistry-competences
Santa Cruz Biotechnology
For experimental / research use only.
(+)-Limonene oxide, mixture of cis and trans, 97%
Treatt
(+)-Limonene Oxide
Kosher
Odor: Sweet, citrus; very slight spearmint and herbaceous notes
Flavor: citrus
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:
Preferred SDS: View
 
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
 
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
 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
Cancer Citations:Search
Toxicology Citations:Search
Env. Mutagen Info. Center: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
 
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
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (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
Haz-Map:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
(R)-
limonene-10-ol
FL/FR
minty
minty
laevo-
carvone
FL/FR
cis-
carvone-5,6-oxide
FL/FR
carvyl acetate
FL/FR
dihydrocarveol
FL/FR
trans-para-
menthan-2-one
FL/FR
tetrahydrocarvone
FL/FR
For Flavor
No flavor group found for these
(R)-
limonene-10-ol
FL/FR
green
green
dihydrocarveol
FL/FR
minty
laevo-
carvone
FL/FR
cis-
carvone-5,6-oxide
FL/FR
carvyl acetate
FL/FR
trans-para-
menthan-2-one
FL/FR
tetrahydrocarvone
FL/FR
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 orange fruit
Search Trop Picture
 pepper japanese pepper
Search Trop Picture
 spearmint oil
Search Trop Picture
 
Synonyms:
7-oxabicyclo[4.1.0]heptane, 1-methyl-4- (1-methylethenyl)-
7-oxabicyclo[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-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan
4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptane
 

Articles:

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.
 
Notes:
Isol. from oil of Cymbopogon spp., orange (Citrus sinensis), Japanese pepper tree (Zanthoxylum piperitum) and others
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