(E)-verbenol
bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2S,5R)-
 
Notes:
None found
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CAS Number: 1820-09-3Picture of molecule3D/inchi
Other(deleted CASRN): 5416-53-5
ECHA EINECS - REACH Pre-Reg: 217-335-5
FDA UNII: 5E8197JSI1
Nikkaji Web: J259.681D
MDL: MFCD00798105
XlogP3-AA: 1.60 (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
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Perfumer and Flavorist: Search
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PubMed: Search
NCBI: Search
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Physical Properties:
Appearance: white to colorless solid to liquid (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 22.00 to  24.00 °C. @ 760.00 mm Hg
Boiling Point: 214.00 to  215.00 °C. @ 760.00 mm Hg
Boiling Point: 22.00 to  23.00 °C. @ 10.00 mm Hg
Vapor Pressure: 0.033000 mmHg @ 25.00 °C. (est)
Flash Point: 184.00 °F. TCC ( 84.44 °C. )
logP (o/w): 2.554 (est)
Soluble in:
 alcohol
 water, 480.4 mg/L @ 25 °C (est)
Insoluble in:
 water
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: flavor and fragrance agents
IFRA Code of Practice Notification of the 49th Amendment to the IFRA Code of Practice
 
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA Substance Registry Services (TSCA): 1820-09-3
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 89664
National Institute of Allergy and Infectious Diseases: Data
 (1S,2R,5S)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
Chemidplus: 0001820093
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References:
 (1S,2R,5S)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 89664
Pubchem (sid): 135046296
Pherobase: View
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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): Search
Typical G.C.
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 ferula cupularis flower oil @ 0.09%
Data  GC  Search Trop  Picture
 layana oil kenya @ 1.07%
Data  GC  Search Trop  Picture
 nepeta betonicifolia c.a. meyer oil turkey @ 0.10%
Data  GC  Search Trop  Picture
 nepeta denudata benth. oil iran @ 3.40%
Data  GC  Search Trop  Picture
 patchouli oil china @ 0.03%
Data  GC  Search Trop  Picture
 wormseed oil spain @ 1.21%
Data  GC  Search Trop  Picture
 wormwood oil italy @ trace%
Data  GC  Search Trop  Picture
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Synonyms:
 bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2S,5R)-rel-
 bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, trans-(+)-
 bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2S,5R)-
(1alpha,2alpha,5alpha)-4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-ol
(1R,2S,5R)-4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-ol
(1R-(1a,2a,5a))-4,6,6-trimethylbicyclo(3.1.1)hept-3-en-2-ol
(1R,2S,5R)-4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
(1S,2R,5S)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
trans-verbenol
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Articles:
PubMed: Reproductive Isolation of Ips nitidus and I. shangrila in Mountain Forests of Western China: Responses to Chiral and Achiral Candidate Pheromone Components.
PubMed: Pheromone Production by an Invasive Bark Beetle Varies with Monoterpene Composition of its Naïve Host.
PubMed: Chemical similarity between historical and novel host plants promotes range and host expansion of the mountain pine beetle in a naïve host ecosystem.
PubMed: Volatile oil of Artemisia santolina decreased morphine withdrawal jumping in mice.
PubMed: Faecal chemical cues in water buffalo that facilitate estrus detection.
PubMed: Bioactivities of volatile components from Nepalese Artemisia species.
PubMed: Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
PubMed: Semiochemical emission from individual galleries of the southern pine beetle, (Coleoptera: Curculionidae: Scolytinae), attacking standing trees.
PubMed: Chemical composition and antioxidant activity of the essential oil of Juniperus phoenicea L. berries.
PubMed: Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.
PubMed: Functional genomics of mountain pine beetle (Dendroctonus ponderosae) midguts and fat bodies.
PubMed: Autoxidation versus biotransformation of alpha-pinene to flavors with Pleurotus sapidus: regioselective hydroperoxidation of alpha-pinene and stereoselective dehydrogenation of verbenol.
PubMed: Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.
PubMed: Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
PubMed: Electrophysiological and behavioral responses of Dendroctonus valens (Coleoptera: Curculionidae: Scolytinae) to four bark beetle pheromones.
PubMed: Synergistic blends of monoterpenes for aggregation pheromones of the mountain pine beetle (Coleoptera: Curculionidae).
PubMed: Attraction of the southern pine beetle, Dendroctonus frontalis, to pheromone components of the western pine beetle, Dendroctonus brevicomis (Coleoptera: Curculionidae: Scolytinae), in an allopatric zone.
PubMed: Analysis by gas chromatography-mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss gathered in Nevakoh and Shahoo, Zagross mountain, West of Iran.
PubMed: Analysis of the essential oil composition of eight Anthemis species from Greece.
PubMed: Olfactory receptor neurons in two Heliothine moth species responding selectively to aliphatic green leaf volatiles, aromatic compounds, monoterpenes and sesquiterpenes of plant origin.
PubMed: Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilised Picea abies cells.
PubMed: Chemical composition and antimicrobial activity of the essential oils from the gum of Turkish pistachio (Pistacia vera L.).
PubMed: Transformation of alpha-pinene using Picea abies suspension culture.
PubMed: Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol.
PubMed: Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
PubMed: Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
PubMed: Renal elimination of verbenols in man following experimental alpha-pinene inhalation exposure.
PubMed: Conversion of verbenols to verbenone by yeasts isolated fromDendroctonus ponderosae (Coleoptera: Scolytidae).
PubMed: Identification of cis- and trans-verbenol in human urine after occupational exposure to terpenes.
PubMed: Secondary attraction and field activity of beetle-produced volatiles inDendroctonus terebrans.
PubMed: Oxygenated monoterpenes produced by yeasts, isolated fromIps typographus (Coleoptera: Scolytidae) and grown in phloem medium.
PubMed: Response of mountain pine beetle,Dendroctonus ponderosae Hopkins, and pine engraver,Ips pint (SAY), to ipsdienol in southwestern British Columbia.
PubMed: Differences in attraction to semiochemicals present in sympatric pine shoot beetles,Tomicus minor andT. piniperda.
PubMed: Semiochemicals produced by western balsam bark beetle,Dryocoetes confusus Swaine (Coleoptera: Scolytidae).
PubMed: Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
PubMed: Electroantennogram responses by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected semiochemicals.
PubMed: Interconversion of verbenols and verbenone by identified yeasts isolated from the spruce bark beetleIps typographus.
PubMed: Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.
PubMed: Attractive and inhibitory pheromones produced in the bark beetle,Dendroctonus brevicomis, during host colonization: Regulation of inter- and intraspecific competition.
PubMed: Single cell responses of the Douglas-fir beetle,Dendroctonus pseudotsugae hopkins (Coleoptera: Scolytidae), to pheromones and host odors.
PubMed: Pheromone production by axenically rearedDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae).
PubMed: Antennal olfactory responsiveness of Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae) to pheromones and host odors.
PubMed: Bark beetle conversion of a plant compound to a sex-specific inhibitor of pheromone attraction.
PubMed: Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
PubMed: Seasonal variation in laboratory response to behavioral chemicals of the southern pine beetle.
PubMed: Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits.
PubMed: Metabolism of alpha- and beta-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula.
PubMed: Selective production of cis- and trans-verbenol from (-)-and (+)-alpha by a bark beetle.
PubMed: Sound production in scolytidae:chemostimulus of sonic signal by the douglas-fir beetle.
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