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linalool oxide

General Material Information

Preferred name linalool oxide
Trivial Name Linalool, oxide
Short Description cis- and trans-linalool oxide
Formula C10 H18 O2
CAS Number 1365-19-1
Deleted CAS Number 11063-76-6
FEMA Number 3746
ECHA Number 215-723-9
FDA UNII 4UJJ55KMCS
Nikkaji Number J354.663B
COE Number 11876
xLogP3-AA 1.80 (est)
NMR Predictor External link
JECFA Food Flavoring 1454 cis- and trans-linalool oxide
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
Synonyms
  • linalool 3,7-oxide
  • linalool dihydroepoxide
  • cis- and trans- linalool oxide
  • linalool oxide (5-ring)
  • linalool oxide natural
  • linalool, epoxydihydro-
  • linalool, oxide
  • (Z,E)-2-methyl-2-vinyl-5-(2-hydroxy-2-propyl) tetrahydrofuran
  • cis,trans-2-methyl-2-vinyl-5-(2-hydroxy-2-propyl) tetrahydrofuran
  • 2-(5-methyl-5-vinyltetrahydro-2-furanyl)-2-propanol
  • a- methyl-a-[4-methyl-3-pentenyl]oxiranemethanol
  • 2-oxiranemethanol, a-methyl-a-(4-methyl-3-penten-1-yl)-
  • (Z,E)-2-vinyl-2-methyl-5-(1-hydroxy-1-methyl ethyl) tetrahydrofuran
  • cis,trans-2-vinyl-2-methyl-5-(1-hydroxy-1-methyl ethyl) tetrahydrofuran
  • (Z,E)-2-vinyl-2-methyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuran
  • cis,trans-2-vinyl-2-methyl-5-(1-hydroxy-1-methylethyl)tetrahydrofuran
  • 2-(5-methyl-5-vinyltetrahydro-2-furanyl)-2-propanol
  • Epoxylinalool

US / EU / FDA / JECFA / FEMA / Scholar / Patents

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Literature & References

2-(5-methyl-5-vinyltetrahydro-2-furanyl)-2-propanol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:1365-19-1
Pubchem (cid):102611
Pubchem (sid):135059203
Flavornet:1365-19-1
Publications by PubMed
Anxiolytic-like effects of inhaled linalool oxide in experimental mouse anxiety models.
The enantiomeric composition of linalool and linalool oxide in the flowers of kiwifruit (Actinidia) species.
Development and assessment of plant-based synthetic odor baits for surveillance and control of malaria vectors.
Effects of volatile compounds emitted by Protea species (proteaceae) on antennal electrophysiological responses and attraction of cetoniine beetles.
Anodic coupling reactions: probing the stereochemistry of tetrahydrofuran formation. A short, convenient synthesis of linalool oxide.
Enantiomeric distribution of major chiral volatile organic compounds in juniper-flavored distillates.
Chemical composition of volatiles from Opuntia littoralis, Opuntia ficus-indica, and Opuntia prolifera growing on Catalina Island, California.
Degradation of terpenes and terpenoids from Mediterranean rangelands by mixed rumen bacteria in vitro.
Compositions of the volatile oils of Citrus macroptera and C. maxima.
Prediction of Muscat aroma in table grape by analysis of rose oxide.
Behavioural and electroantennogram responses of the stable fly (Stomoxys calcitrans L.) to plant essential oils and their mixtures with attractants.
Relationship of sensory and instrumental aroma measurements of dark chocolate as influenced by fermentation method, roasting and conching conditions.
Bioorganic diversity of rare Coriandrum sativum L. honey: unusual chromatographic profiles containing derivatives of linalool/oxygenated methoxybenzene.
Characterization of volatile components of tea flowers (Camellia sinensis) growing in Kangra by GC/MS.
Jasmonate-Mediated Induced Volatiles in the American Cranberry, Vaccinium macrocarpon: From Gene Expression to Organismal Interactions.
Evaluation of volatiles from Ampelopsis brevipedunculata var. heterophylla using GC-olfactometry, GC-MS and GC-pulsed flame photometric detector.
Comparison of chemical composition and antibacterial activity of lavender varieties from Poland.
Integrated bioprocess for the stereospecific production of linalool oxides from linalool with Corynespora cassiicola DSM 62475.
Characterization of aroma compounds in Chinese bayberry (Myrica rubra Sieb. et Zucc.) by gas chromatography mass spectrometry (GC-MS) and olfactometry (GC-O).
The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia.
Composition of a monoterpenoid-rich essential oil from the rhizome of Zingiber officinale from north western Himalayas.
Volatile fraction of lavender and bitter fennel infusion extracts.
Identification and field evaluation of grape shoot volatiles attractive to female grape berry moth (Paralobesia viteana).
Characterization of two distinct glycosyl hydrolase family 78 alpha-L-rhamnosidases from Pediococcus acidilactici.
Cereal crop volatile organic compound induction after mechanical injury, beetle herbivory (Oulema spp.), or fungal infection (Fusarium spp.).
Effectiveness of different solid-phase microextraction fibres for differentiation of selected Madeira island fruits based on their volatile metabolite profile--identification of novel compounds.
Essential oil composition and variability of Hypericum perforatum from wild populations of northern Turkey.
Volatiles from a rare Acer spp. honey sample from Croatia.
Bound volatile precursors in genotypes in the pedigree of 'Marion' blackberry (Rubus sp.).
Lemongrass effects on IL-1beta and IL-6 production by macrophages.
Evaluating the use of male-produced pheromone components and plant volatiles in two trap designs to monitor Anoplophora glabripennis.
Floral scent of Canada thistle and its potential as a generic insect attractant.
Fungal biotransformation of (+/-)-linalool.
Simultaneous Distillation Extraction of Some Volatile Flavor Components from Pu-erh Tea Samples-Comparison with Steam Distillation-Liquid/Liquid Extraction and Soxhlet Extraction.
[Study on chemical constituents and antimicrobial activity of the essential oil from Acanthopanax brachypus].
Floral odors of Silene otites: their variability and attractiveness to mosquitoes.
Biotransformation of (S)-(+)-linalool by Aspergillus niger: an investigation of the culture conditions.
Biotransformation of linalool to furanoid and pyranoid linalool oxides by Aspergillus niger.
Study on the cytochrome P450-mediated oxidative metabolism of the terpene alcohol linalool: indication of biological epoxidation.
Application of HS-SPME and GC-MS to characterization of volatile compounds emitted from Osmanthus flowers.
Variation of major volatile constituents in various green teas from Southeast Asia.
Antifungal activities of major tea leaf volatile constituents toward Colletorichum camelliae Massea.
Grapefruit gland oil composition is affected by wax application, storage temperature, and storage time.
Screening of volatile composition from Portuguese multifloral honeys using headspace solid-phase microextraction-gas chromatography-quadrupole mass spectrometry.
Quantitation of free and glycosidically bound volatiles in and effect of glycosidase addition on three tomato varieties (Solanum lycopersicum L.).
Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae).
Volatile emissions from Aesculus hippocastanum induced by mining of larval stages of Cameraria ohridella influence oviposition by conspecific females.
Rapid determination of volatile compounds emitted from Chimonanthus praecox flowers by HS-SPME-GC-MS.
Antennal responses to floral scents in the butterfly Heliconius melpomene.
Investigation of bound aroma constituents of yellow-fleshed nectarines (Prunus persica L. Cv. Springbright). changes in bound aroma profile during maturation.
Investigation of the skin sensitizing activity of linalool.
Oxidative cyclization based on reversing the polarity of enol ethers and ketene dithioacetals. Construction of a tetrahydrofuran ring and application to the synthesis of (+)-nemorensic Acid.
Volatile compounds emitted by sclerotia of Sclerotinia minor, Sclerotinia sclerotiorum, and Sclerotium rolfsii.
Electroantennogram responses ofHyles lineata (Sphingidae: Lepidoptera) to volatile compounds fromClarkia breweri (Onagraceae) and other moth-pollinated flowers.
Metabolism of monoterpene alcohol, linalool, by a soil pseudomonad.
Manipulating volatile emission in tobacco leaves by expressing Aspergillus nigerbeta-glucosidase in different subcellular compartments.
[Studies on the chemical constituents of the volatiles of Clerodendron bungei].
Chemical composition of anther volatiles in Ranunculaceae: genera-specific profiles in Anemone, Aquilegia, Caltha, Pulsatilla, Ranunculus, and Trollius species.
Fragrances in oolong tea that enhance the response of GABAA receptors.
Semiochemicals from the predatory stink bug Eocanthecona furcellata (Wolff): components of metathoracic gland, dorsal abdominal gland, and sternal gland secretions.
Volatiles from Ficus hispida and their attractiveness to fig wasps.
(Z)-3-hexenyl and trans-linalool 3,7-oxide beta-primeverosides isolated as aroma precursors from leaves of a green tea cultivar.
Similarities in the aroma chemistry of Gewürztraminer variety wines and lychee (Litchi chinesis sonn.) fruit.

Other Information

(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB35365
FooDB:FDB021839
Export Tariff Code:2932.19.0000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
EFSA Update of results on the monitoring of furan levels in food:Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:Read Report

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 170.25186157227
Specific gravity @ 25 °C
Pounds per Gallon 7.755 to 7.838
Refractive Index 1.451 to 1.456 @ 20 °C
Vapor Pressure 0.002 mmHg @ 25 °C
Flash Point TCC Value 62.78 °C TCC
logP (o/w) 1.375 est
Shelf life 24 months (or longer if stored properly.)
Storage notes Store in cool, dry place in tightly sealed containers, protected from heat and light.
Solubility
alcohol Yes
water, 1669 mg/L @ 25 °C (est) Yes
water No
Stability
detergent Unspecified
soap Unspecified

Organoleptic Properties

Odor Type: Floral
floral, herbal, earthy, green, woody, cooling, terpenic
Odor strength medium
Substantivity 12 hour(s) at 100.00 %
Luebke, William tgsc, (2003) At 100.00 %. floral herbal earthy green
Mosciano, Gerard P&F 22, No. 3, 47, (1997) Woody, floral, cooling, terpy and slightly green
Flavor Type: Green
green, floral, fatty, woody, fermented, herbal, fruity, berry
Mosciano, Gerard P&F 22, No. 3, 47, (1997) At 50.00 ppm. Green, floral, fatty, woody, fermented, herbal, fruity and berry
General comment Floreal, fruity

Occurrences

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 36/38 - Irritating to skin and eyes.
S 02 - Keep out of the reach of children.
S 20/21 - When using do not eat, drink or smoke.
S 24/25 - Avoid contact with skin and eyes.
S 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S 37/39 - Wear suitable gloves and eye/face protection.
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
Acute toxicity, Oral (Category 4), H302
GHS Label elements, including precautionary statements
Pictogramexclamation-mark.jpg
Signal word Warning
Hazard statement(s)
H302 - Harmful if swallowed
H313 - May be harmful in contact with skin
H314 - Causes severe skin burns and eye damage
Precautionary statement(s)
P264 - Wash skin thouroughly after handling.
P270 - Do not eat, drink or smoke when using this product.
P280 - Wear protective gloves/protective clothing/eye protection/face protection.
P301 + P312 - IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305 + P351 + P338 - IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P310 - Immediately call a POISON CENTER or doctor/physician.
P330 - Rinse mouth.
P501 - Dispose of contents/ container to an approved waste disposal plant.
Oral/Parenteral Toxicity:
oral-rat LD50 1150 mg/kg
(Moreno, 1977acr)

oral-rat LD50 [sex: M,F] 2210 mg/kg
(Colaianni, 1967)

Dermal Toxicity:
skin-rabbit LD50 2500 mg/kg
(Reagan & Becci, 1984j)

Inhalation Toxicity:
Not determined

Safety in use information

Category:
flavor and fragrance agents
RIFM Fragrance Material Safety Assessment: Search
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
Recommendation for linalool oxide usage levels up to:
5.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 72.50 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 14.00 (μg/capita/day)
Structure Class: II
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: 14
Click here to view publication 14
average usual ppmaverage maximum ppm
baked goods: -11.25000
beverages(nonalcoholic): -3.86000
beverages(alcoholic): -6.75000
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -7.00000
fruit ices: --
gelatins / puddings: -4.61000
granulated sugar: --
gravies: --
hard candy: --
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: -10.17800
soups: --
sugar substitutes: --
sweet sauces: --

Safety references

European Food Safety Athority(EFSA):Flavor usage levels; Subacute, Subchronic, Chronic and Carcinogenicity Studies; Developmental / Reproductive Toxicity Studies; Genotoxicity Studies...

European Food Safety Authority (EFSA) reference(s):

Flavouring Group Evaluation 33 (FGE.33)[1] - Six Tetrahydrofuran Derivatives from Chemical Groups 13, 14, 16 and 26 - Scientific Opinion of the Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food
View page or View pdf

Flavouring Group Evaluation 75 (FGE.75)[1] - Consideration of tetrahydrofuran derivatives and a furanone derivative evaluated by JECFA (63rd meeting) structurally related to tetrahydrofuran derivatives evaluated by EFSA in FGE.33 (2008)
View page or View pdf

Scientific Opinion on the safety and efficacy of furanones and tetrahydrofurfuryl derivatives: 4-hydroxy-2,5-dimethylfuran-3(2H)-one, 4,5-dihydro-2-methylfuran-3(2H)-one, 4-acetoxy-2,5-dimethylfuran-3(2H)-one and linalool oxide (chemical group 13) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on the safety and efficacy of furanones and tetrahydrofurfuryl derivatives: 5-ethyl-3-hydroxy-4-methylfuran-2(5H)-one and 3-hydroxy-4,5-dimethylfuran-2(5H)-one (chemical group 13) when used as flavourings for all animal species
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 75, Revision 1 (FGE.75Rev1): Consideration of tetrahydrofuran derivatives evaluated by JECFA (63rd meeting) structurally related to tetrahydrofuran derivatives evaluated by EFSA in FGE.33 (2008)
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):1365-19-1
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :102611
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
2-(5-methyl-5-vinyltetrahydro-2-furanyl)-2-propanol
Chemidplus:0001365191
RTECS:OI7782000 for cas# 1365-19-1