dextro-limonene oxide
L-8-p-menthene-1,2-epoxide
 
Notes:
None found
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      Product(s):
      203719-54-4 (+)-Limonene 1,2-epoxide
       
  • R C Treatt & Co Ltd
    • R C Treatt and Co Ltd
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      Product(s):
      d-Limonene oxide

      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.
       
       
Synonyms   Articles   Notes   Search
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 (SATF):203719-54-4 ; D-8-P-MENTHENE-1,2-EPOXIDE
Synonyms   Articles   Notes   Search   Top
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 mmHg @ 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
Synonyms   Articles   Notes   Search   Top
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).
 
 
Synonyms   Articles   Notes   Search   Top
Cosmetic Information:
None found
Synonyms   Articles   Notes   Search   Top
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%
Synonyms   Articles   Notes   Search   Top
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
Synonyms   Articles   Notes   Search   Top
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
Click here to view publication 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: --
Synonyms   Articles   Notes   Search   Top
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
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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
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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 Substances Added to Food (formerly 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
Synonyms   Articles   Notes   Search   Top
Potential Blenders and core components note
 
For Odor
aldehydic
 dodecanal (aldehyde C-12 lauric)FL/FR
(Z)-4-dodecenalFL/FR
 green hexanalFL/FR
 undecanalFL/FR
anisic
 amyl furoateFL/FR
citrus
 citral diethyl acetalFL/FR
 citral dimethyl acetalFL/FR
(R)-citronellyl nitrileFR
 citronitrile (Symrise)FR
isodecyl acetateFR
2-dodecanoneFL/FR
 lemon verbena oil 
 limonene aldehydeFR
 limonene oxideFL/FR
 litsea cubeba fruit oilFL/FR
 methyl heptenoneFL/FR
(Z+E)-2-methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehydeFL/FR
1-methyl-4-methyl ethenyl cyclohexene sulfurizedFL/FR
alpha-methylene citronellalFR
 petitgrain specialtyFR
 tangerine acetateFR
creamy
3-heptyl dihydro-5-methyl-2(3H)-furanoneFL/FR
earthy
 spathulenol 
ethereal
 ethyl 4-pentenoateFL/FR
fatty
6-methyl-5-hepten-2-one propylene glycol acetalFL/FR
floral
 aglaia odorata absoluteFR
isoamyl angelateFL/FR
alpha-amyl cinnamaldehydeFL/FR
 bursera graveolens wood oilFL/FR
 cassis cyclohexeneFR
 citronellolFL/FR
 citronellyl acetateFL/FR
 coriander seed oil terpenelessFL/FR
 dihydrocitronellyl ethyl etherFR
 dimethyl benzyl carbinyl butyrateFL/FR
 geranyl tiglateFL/FR
 jasmin absolute egypt (from concrete)FL/FR
 magnolia flower oil CO2 extractFL/FR
 menthadienyl formateFR
 methyl benzyl acetate (mixed ortho-,meta-,para-)FL/FR
 methyl nerate 
 muguet specialtyFR
(E)-nerolidolFL/FR
 nonan-3-yl acetateFL/FR
 petitgrain fragranceFR
 petitgrain oil paraguayFL/FR
 terpinyl formateFL/FR
(E)-2,5,9-trimethyl-4,9-decadien-1-alFR
fruity
isoamyl 2-methyl butyrateFL/FR
para-anisyl propionateFL/FR
 balsam specialtyFR
isobutyl 2-methyl butyrateFL/FR
 ethyl citronellateFL/FR
 methyl acetoacetateFL/FR
2-methyl butyl isovalerateFL/FR
sesquiphellandrene 
 tropical specialtyFR
green
isobutyl heptanoateFL/FR
isobutyl methyl ketoneFL/FR
 citrus carbaldehyde / methyl anthranilate schiff's baseFR
black currant bud absolute replacerFL/FR
 dicyclopentadiene propionateFR
 green carboxylateFR
 herbal cyclohexaneFR
 hexyl tiglateFL/FR
(2-methoxy-1-methyl butyl) benzeneFR
 octanal diethyl acetalFL/FR
 octanal dimethyl acetalFL/FR
(E)-2-octen-1-olFL/FR
herbal
isoamyl heptanoateFL/FR
 artemisia ludoviciana oilFR
 buchu mercaptan acetateFL/FR
 bursera graveolens wood 
 butyl levulinateFL/FR
 chamomile propionateFR
 chamomile valerateFR
 dimethyl benzyl carbinyl crotonateFL/FR
2-dodecenalFL/FR
 linalyl formateFL/FR
 marigold absolute (tagetes patula)FR
1-para-menthen-9-yl acetateFL/FR
6-methoxy-2,6-dimethyl octanalFR
(1S,5R)-myrtenyl acetateFL/FR
 myrtle oilFL/FR
3-octanon-1-olFL/FR
beta-sesquiphellandrene 
 rue flower oil colombia 
 rue oilFL/FR
 rue oil cubaFL/FR
 tagete oil CO2 extractFL/FR
 tagete oil egyptFL/FR
 tagete oil rwandaFL/FR
 tagete oil turkeyFL/FR
 tagete oil zambiaFL/FR
 tricyclodecenyl isobutyrateFR
 tricyclodecenyl propionateFR
minty
laevo-carvoneFL/FR
 carvyl acetateFL/FR
 dihydrocarveolFL/FR
orris
 orris capronateFL/FR
terpenic
alpha-phellandreneFL/FR
waxy
 decanal dimethyl acetalFL/FR
3-decanoneFL/FR
woody
 bamboo fragranceFR
2-decalinyl acetateFR
 humulus lupulus extractFL/FR
 patchouli absoluteFR
 
For Flavor
 
No flavor group found for these
isoamyl angelateFL/FR
 amyl furoateFL/FR
para-anisyl propionateFL/FR
 benzyl methyl tiglateFL
 bursera graveolens wood 
 bursera graveolens wood oilFL/FR
isobutyl heptanoateFL/FR
beta-cubebeneFL
 decanal dimethyl acetalFL/FR
3-decanoneFL/FR
(±)-(cis+trans)-1,2-dihydroperillaldehydeFL
 dimethyl benzyl carbinyl crotonateFL/FR
(Z)-4-dodecenalFL/FR
 ethyl 4-pentenoateFL/FR
 lemon verbena oil 
 limonene oxideFL/FR
 linalyl formateFL/FR
 magnolia flower oil CO2 extractFL/FR
3-mercaptooctanalFL
 methyl acetoacetateFL/FR
 methyl benzyl acetate (mixed ortho-,meta-,para-)FL/FR
 methyl nerate 
(Z+E)-2-methyl-2-(4-methyl-3-pentenyl) cyclopropane carbaldehydeFL/FR
6-methyl-5-hepten-2-one propylene glycol acetalFL/FR
 nonan-3-yl acetateFL/FR
3-octanon-1-olFL/FR
beta-sesquiphellandrene 
sesquiphellandrene 
 rue flower oil colombia 
 spathulenol 
 althaea officinalis root tinctureFL
citrus
 citral diethyl acetalFL/FR
 citral dimethyl acetalFL/FR
 dehydronootkatoneFL
 litsea cubeba fruit oilFL/FR
1-methyl-4-methyl ethenyl cyclohexene sulfurizedFL/FR
creamy
 althaea officinalis root extractFL
dusty
 ethyl citronellateFL/FR
fatty
2-dodecanoneFL/FR
2-dodecenalFL/FR
(E)-2-octen-1-olFL/FR
floral
 citronellolFL/FR
 citronellyl acetateFL/FR
 dimethyl benzyl carbinyl butyrateFL/FR
 geranyl tiglateFL/FR
 jasmin absolute egypt (from concrete)FL/FR
fruity
isoamyl 2-methyl butyrateFL/FR
 buchu mercaptan acetateFL/FR
isobutyl 2-methyl butyrateFL/FR
black currant bud absolute replacerFL/FR
3-heptyl dihydro-5-methyl-2(3H)-furanoneFL/FR
1-para-menthen-9-yl acetateFL/FR
2-methyl butyl isovalerateFL/FR
 tagete oil CO2 extractFL/FR
 tagete oil rwandaFL/FR
 tagete oil turkeyFL/FR
 tagete oil zambiaFL/FR
 terpinyl formateFL/FR
green
isobutyl methyl ketoneFL/FR
 dihydrocarveolFL/FR
(E)-2-heptenalFL
 hexyl tiglateFL/FR
 methyl heptenoneFL/FR
(E)-nerolidolFL/FR
(E,E)-2,6-nonadienalFL
2,4-octadienalFL
 octanal diethyl acetalFL/FR
 octanal dimethyl acetalFL/FR
herbal
isoamyl heptanoateFL/FR
 butyl levulinateFL/FR
 coriander seed oil terpenelessFL/FR
 green hexanalFL/FR
 petitgrain oil paraguayFL/FR
 rue oilFL/FR
 rue oil cubaFL/FR
 tagete oil egyptFL/FR
minty
laevo-carvoneFL/FR
 carvyl acetateFL/FR
orris
 orris capronateFL/FR
soapy
 dodecanal (aldehyde C-12 lauric)FL/FR
spicy
 myrtle oilFL/FR
terpenic
alpha-phellandreneFL/FR
tropical
alpha-amyl cinnamaldehydeFL/FR
waxy
 undecanalFL/FR
woody
 humulus lupulus extractFL/FR
(1S,5R)-myrtenyl acetateFL/FR
 
Synonyms   Articles   Notes   Search   Top
Potential Uses:
 beverageFL
 citrusFR
 dairyFL
 mintFR
Synonyms   Articles   Notes   Search   Top
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   Articles   Notes   Search   Top
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
Synonyms   Articles   Notes   Search   Top
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.
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