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

dextro-limonene oxide
L-8-p-menthene-1,2-epoxide

Supplier Sponsors

Name:(4R)-1-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
CAS Number: 203719-54-4Picture of molecule3D/inchi
FDA UNII:278IM94GXB
Nikkaji Web:J185.800I
Beilstein Number:0080231
MDL:MFCD00074770
XlogP3-AA:2.50 (est)
Molecular Weight:152.23672000
Formula:C10 H16 O
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
FEMA Number:4656 L-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 sum of isomers
Food Chemicals Codex Listed: No
Boiling Point: 197.00 to 198.00 °C. @ 760.00 mm Hg
Boiling Point: 113.00 to 114.00 °C. @ 50.00 mm Hg
Vapor Pressure:0.515000 mm/Hg @ 25.00 °C. (est)
Flash Point: 150.00 °F. TCC ( 65.56 °C. )
logP (o/w): 3.200 (est)
Soluble in:
 alcohol
 water, 137.2 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: green
Odor Strength:medium
green citrus fruity
Odor Description:at 100.00 %. green citrus fruity
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
CHEMSTEP
7-Oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (4R)- (9CI)
Nippon Terpene Chemicals
d-Limonene oxide 95% up (cis+trans)
R C Treatt & Co Ltd
d-Limonene oxide
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.
Sigma-Aldrich: Aldrich
For experimental / research use only.
(+)-Limonene 1,2-epoxide ≥97.0%
purum, mixture of cis/trans-isomers
Sigma-Aldrich: Aldrich
For experimental / research use only.
(+)-Limonene oxide, mixture of cis and trans 97%
 
Safety Information:
Preferred SDS: View
European information :
Most important hazard(s):
None - None found.
S 02 - Keep out of the reach of children.
S 24/25 - Avoid contact with skin and eyes.
 
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-mouse LD50 2700 ul/kg

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category: flavor and fragrance agents
Recommendation for dextro-limonene oxide usage levels up to:
  2.0000 % in the fragrance concentrate.
 
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): 0.100000.50000
beverages(alcoholic): 0.200001.00000
breakfast cereal: --
cheese: --
chewing gum: 1.000005.00000
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: --
fruit ices: --
gelatins / puddings: 0.200001.00000
granulated sugar: --
gravies: --
hard candy: 0.500002.50000
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:
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):203719-54-4
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :441245
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(4R)-1-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
Chemidplus:0203719544
 
References:
 (4R)-1-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:203719-54-4
Pubchem (cid):441245
Pubchem (sid):9480
 
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
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
KEGG (GenomeNet):C07271
HMDB (The Human Metabolome Database):Search
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
For Odor
aldehydic
dodecanal (aldehyde C-12 lauric)
FL/FR
(Z)-4-
dodecenal
FL/FR
green hexanal
FL/FR
undecanal
FL/FR
anisic
amyl furoate
FL/FR
citrus
citral diethyl acetal
FL/FR
citral dimethyl acetal
FL/FR
(R)-
citronellyl nitrile
FR
citronitrile (Symrise)
FR
iso
decyl acetate
FR
2-
dodecanone
FL/FR
limonene aldehyde
FR
limonene oxide
FL/FR
litsea cubeba fruit oil
FL/FR
methyl heptenone
FL/FR
(Z+E)-2-
methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehyde
FL/FR
1-
methyl-4-methyl ethenyl cyclohexene sulfurized
FL/FR
alpha-
methylene citronellal
FR
petitgrain specialty
FR
tangerine acetate
FR
creamy
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
ethereal
ethyl 4-pentenoate
FL/FR
fatty
6-
methyl-5-hepten-2-one propylene glycol acetal
FL/FR
floral
aglaia odorata absolute
FR
iso
amyl angelate
FL/FR
alpha-
amyl cinnamaldehyde
FL/FR
bursera graveolens wood oil
FL/FR
cassis cyclohexene
FR
citronellol
FL/FR
citronellyl acetate
FL/FR
coriander seed oil terpeneless
FL/FR
dihydrocitronellyl ethyl ether
FR
dimethyl benzyl carbinyl butyrate
FL/FR
geranyl tiglate
FL/FR
jasmin absolute egypt (from concrete)
FL/FR
magnolia flower oil CO2 extract
FL/FR
menthadienyl formate
FR
methyl benzyl acetate (mixed ortho-,meta-,para-)
FL/FR
muguet specialty
FR
(E)-
nerolidol
FL/FR
nonan-3-yl acetate
FL/FR
petitgrain fragrance
FR
petitgrain oil paraguay
FL/FR
terpinyl formate
FL/FR
(E)-2,5,9-
trimethyl-4,9-decadien-1-al
FR
fruity
iso
amyl 2-methyl butyrate
FL/FR
para-
anisyl propionate
FL/FR
balsam specialty
FR
iso
butyl 2-methyl butyrate
FL/FR
ethyl citronellate
FL/FR
methyl acetoacetate
FL/FR
2-
methyl butyl isovalerate
FL/FR
tropical specialty
FR
green
iso
butyl heptanoate
FL/FR
iso
butyl methyl ketone
FL/FR
citrus carbaldehyde / methyl anthranilate schiff's base
FR
black
currant bud absolute replacer
FL/FR
dicyclopentadiene propionate
FR
green carboxylate
FR
herbal cyclohexane
FR
hexyl tiglate
FL/FR
(2-
methoxy-1-methyl butyl) benzene
FR
octanal diethyl acetal
FL/FR
octanal dimethyl acetal
FL/FR
(E)-2-
octen-1-ol
FL/FR
herbal
iso
amyl heptanoate
FL/FR
artemisia ludoviciana oil
FR
buchu mercaptan acetate
FL/FR
butyl levulinate
FL/FR
chamomile propionate
FR
chamomile valerate
FR
dimethyl benzyl carbinyl crotonate
FL/FR
2-
dodecenal
FL/FR
linalyl formate
FL/FR
marigold absolute (tagetes patula)
FR
1-para-
menthen-9-yl acetate
FL/FR
6-
methoxy-2,6-dimethyl octanal
FR
(1S,5R)-
myrtenyl acetate
FL/FR
myrtle oil
FL/FR
3-
octanon-1-ol
FL/FR
rue oil
FL/FR
rue oil cuba
FL/FR
tagete oil CO2 extract
FL/FR
tagete oil egypt
FL/FR
tagete oil rwanda
FL/FR
tagete oil turkey
FL/FR
tagete oil zambia
FL/FR
tricyclodecenyl isobutyrate
FR
tricyclodecenyl propionate
FR
minty
laevo-
carvone
FL/FR
carvyl acetate
FL/FR
dihydrocarveol
FL/FR
orris
orris capronate
FL/FR
terpenic
alpha-
phellandrene
FL/FR
waxy
decanal dimethyl acetal
FL/FR
3-
decanone
FL/FR
woody
bamboo fragrance
FR
2-
decalinyl acetate
FR
humulus lupulus extract
FL/FR
patchouli absolute
FR
For Flavor
No flavor group found for these
iso
amyl angelate
FL/FR
amyl furoate
FL/FR
para-
anisyl propionate
FL/FR
benzyl methyl tiglate
FL
bursera graveolens wood oil
FL/FR
iso
butyl heptanoate
FL/FR
beta-
cubebene
FL
decanal dimethyl acetal
FL/FR
3-
decanone
FL/FR
(±)-(cis+trans)-1,2-
dihydroperillaldehyde
FL
dimethyl benzyl carbinyl crotonate
FL/FR
(Z)-4-
dodecenal
FL/FR
ethyl 4-pentenoate
FL/FR
limonene oxide
FL/FR
linalyl formate
FL/FR
magnolia flower oil CO2 extract
FL/FR
3-
mercaptooctanal
FL
methyl acetoacetate
FL/FR
methyl benzyl acetate (mixed ortho-,meta-,para-)
FL/FR
(Z+E)-2-
methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehyde
FL/FR
6-
methyl-5-hepten-2-one propylene glycol acetal
FL/FR
nonan-3-yl acetate
FL/FR
3-
octanon-1-ol
FL/FR
althaea officinalis root tincture
FL
citrus
citrus
citral diethyl acetal
FL/FR
citral dimethyl acetal
FL/FR
dehydronootkatone
FL
litsea cubeba fruit oil
FL/FR
1-
methyl-4-methyl ethenyl cyclohexene sulfurized
FL/FR
creamy
althaea officinalis root extract
FL
dusty
ethyl citronellate
FL/FR
fatty
2-
dodecanone
FL/FR
2-
dodecenal
FL/FR
(E)-2-
octen-1-ol
FL/FR
floral
citronellol
FL/FR
citronellyl acetate
FL/FR
dimethyl benzyl carbinyl butyrate
FL/FR
geranyl tiglate
FL/FR
jasmin absolute egypt (from concrete)
FL/FR
fruity
iso
amyl 2-methyl butyrate
FL/FR
buchu mercaptan acetate
FL/FR
iso
butyl 2-methyl butyrate
FL/FR
black
currant bud absolute replacer
FL/FR
3-
heptyl dihydro-5-methyl-2(3H)-furanone
FL/FR
1-para-
menthen-9-yl acetate
FL/FR
2-
methyl butyl isovalerate
FL/FR
tagete oil CO2 extract
FL/FR
tagete oil rwanda
FL/FR
tagete oil turkey
FL/FR
tagete oil zambia
FL/FR
terpinyl formate
FL/FR
green
iso
butyl methyl ketone
FL/FR
dihydrocarveol
FL/FR
(E)-2-
heptenal
FL
hexyl tiglate
FL/FR
methyl heptenone
FL/FR
(E)-
nerolidol
FL/FR
(E,E)-2,6-
nonadienal
FL
2,4-
octadienal
FL
octanal diethyl acetal
FL/FR
octanal dimethyl acetal
FL/FR
herbal
iso
amyl heptanoate
FL/FR
butyl levulinate
FL/FR
coriander seed oil terpeneless
FL/FR
green hexanal
FL/FR
petitgrain oil paraguay
FL/FR
rue oil
FL/FR
rue oil cuba
FL/FR
tagete oil egypt
FL/FR
minty
laevo-
carvone
FL/FR
carvyl acetate
FL/FR
orris
orris capronate
FL/FR
soapy
dodecanal (aldehyde C-12 lauric)
FL/FR
spicy
myrtle oil
FL/FR
terpenic
alpha-
phellandrene
FL/FR
tropical
alpha-
amyl cinnamaldehyde
FL/FR
waxy
undecanal
FL/FR
woody
humulus lupulus extract
FL/FR
(1S,5R)-
myrtenyl acetate
FL/FR
 
Potential Uses:
FLbeverage
 citrus
FLdairy
 mint
 
Occurrence (nature, food, other):note
 cardamom
Search Trop Picture
 celery seed oil CO2 extract india @ 0.01%
Data GC Search Trop Picture
 celery seed oil india @ 0.08%
Data GC Search Trop Picture
 currant black currant bud
Search Trop Picture
 ferula cupularis stem oil @ 1.89%
Data GC Search Trop Picture
 ginger
Search Trop Picture
 hyptis spicigera lam. oil mali @ trace-0.10%
Data GC Search Trop Picture
 juniper needle oil @ <0.10%
Data GC Search Trop Picture
 lemongrass oil yunnan @ 6.43%
Data GC Search Trop Picture
 mandarin
Search Trop Picture
 orange fruit
Search Trop Picture
 pepper black pepper seed
Search Trop Picture
 tomato leaf
Search Trop Picture
 wormwood oil annus vietnam @ 2.93%
Data GC Search Trop Picture
 
Synonyms:
7-oxabicyclo[4.1.0]heptane, 1-methyl-4-(1-methylethenyl)-, (4R)- (9CI)
D-1,2-epoxy-p-menth-8-ene
dextro-1,2-epoxy-para-menth-8-ene
D-1,2-epoxylimonene
dextro-1,2-epoxylimonene
(+)-limonene 1,2-epoxide
D-limonene 1,2-epoxide
dextro-limonene 1,2-epoxide
D-limonene 1,2-oxide
dextro-limonene 1,2-oxide
D-limonene epoxide
dextro-limonene epoxide
D-limonene monoxide
dextro-limonene monoxide
(+)-limonene oxide
D-limonene oxide
(4R)-limonene-1,2-epoxide
D-8-p-menthene-1,2-epoxide
dextro-8-para-menthene-1,2-epoxide
L-8-p-menthene-1,2-epoxide
(4R)-1-methyl-3-(1-methyl ethenyl)-7-oxabicyclo(4.1.0)heptane
(4R)-1-methyl-3-(1-methyl vinyl)-7-oxabicyclo(4.1.0)heptane
(4R)-1-methyl-3-(prop-1-en-2-yl)-7-oxabicyclo(4.1.0)heptane
(4R)-1-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
 

Articles:

PubMed:Study of ozone-initiated limonene reaction products by low temperature plasma ionization mass spectrometry.
PubMed:Olfactory discrimination ability of South African fur seals (Arctocephalus pusillus) for enantiomers.
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: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: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: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:Stereoselective biotransformation of limonene and limonene oxide by cyanobacterium, Synechococcus sp. PCC 7942.
PubMed:[Terpenoids in root exudates of different allelopathic rice varieties].
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:Patch testing with oxidized R-(+)-limonene and its hydroperoxide fraction.
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: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: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:Air oxidation of d-limonene (the citrus solvent) creates potent allergens.
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.
 
Notes:
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