dextro-limonene oxide

CAS: 203719-54-4 C10 H16 O MW: 152.23672000 green

Identification

Namedextro-limonene oxide
IUPAC(4R)-1-methyl-3-prop-1-en-2-yl-7-oxabicyclo[4.1.0]heptane
CAS Number203719-54-4
FDA UNII278IM94GXB
Molecular FormulaC10 H16 O
Molecular Weight152.23672000
MDL NumberMFCD00074770
Nikkaji NumberJ185.800I
Beilstein0080231

Regulatory

FEMA Number4656
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 sum of isomers
Food Chemicals Codex Listed No
Boiling Point 197.00 to 198.00 °C. @ 760.00 mm Hg, 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
Insoluble in water

Organoleptic Properties

Odor Description at 100.00 %.

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-mouse LD50 2700 ul/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
Recommendation for dextro-limonene oxide usage levels up to2.0000 % in the fragrance concentrate.
baked goods-
beverages(nonalcoholic)0.10000
beverages(alcoholic)0.20000
breakfast cereal-
cheese-
chewing gum1.00000
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings0.20000
granulated sugar-
gravies-
hard candy0.50000
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-

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Potential Uses

FL beverage FR citrus FL dairy FR mint

Natural Occurrence

cardamom celery seed oil CO2 extract india @ 0.01% Data celery seed oil india @ 0.08% Data currant black currant bud ferula cupularis stem oil @ 1.89% Data ginger hyptis spicigera lam. oil mali @ trace-0.10% Data juniper needle oil @ <0.10% Data lemongrass oil yunnan @ 6.43% Data mandarin orange fruit pepper black pepper seed tomato leaf wormwood oil annus vietnam @ 2.93% Data

Synonyms

7-oxa bicyclo[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 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.