(Z)-verbenol
bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2R,5R)-
 
Notes:
None found
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CAS Number: 1845-30-3Picture of molecule3D/inchi
FDA UNII: T0QZZ8E09C
Nikkaji Web: J317.773D
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:
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Physical Properties:
Appearance: white crystals (est)
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Melting Point: 70.00 to  72.00 °C. @ 760.00 mm Hg
Boiling Point: 214.00 to  215.00 °C. @ 760.00 mm Hg
Boiling Point: 89.00 to  91.00 °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
Chemical Carcinogenesis Research Information System: Search
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 164888
National Institute of Allergy and Infectious Diseases: Data
 (1R,2R,5R)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
Chemidplus: 001845303
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References:
 (1R,2R,5R)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 164888
Pubchem (sid): 135120777
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
 boldo leaf oil italy @ trace%
Data  GC  Search Trop  Picture
 boldus leaf oil chile @ 9.90%
Data  GC  Search Trop  Picture
 ferula cupularis flower oil @ 0.70%
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 ferula cupularis stem oil @ 0.30%
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 layana oil kenya @ trace%
Data  GC  Search Trop  Picture
 marjoram oil spain @ 0.10%
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 sage oil england @ 0.70%
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Synonyms:
 bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2R,5R)-rel-
 bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-, (1R,2R,5R)-
(1alpha,2beta,5alpha)-4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-ol
(1R,2R,5R)-rel-4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-ol
(1R,2R,5R)-4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
cis-verbenol
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Articles:
PubMed: Smoke, pheromone and kairomone olfactory receptor neurons in males and females of the pine sawyer Monochamus galloprovincialis (Olivier) (Coleoptera: Cerambycidae).
PubMed: Reproductive Isolation of Ips nitidus and I. shangrila in Mountain Forests of Western China: Responses to Chiral and Achiral Candidate Pheromone Components.
PubMed: Gut-Associated Bacteria of Dendroctonus valens and their Involvement in Verbenone Production.
PubMed: Chemical composition and anti-inflammatory activities of the essential oils from Acacia mearnsii de Wild.
PubMed: Electrophysiological and behavioural responses of the tea geometrid Ectropis obliqua (Lepidoptera: Geometridae) to volatiles from a non-host plant, rosemary, Rosmarinus officinalis (Lamiaceae).
PubMed: Chemical composition and general toxicity of essential oils extracted from the aerial parts of Artemisia armeniaca Lam. and A. incana (L.) Druce growing in Iran.
PubMed: Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity.
PubMed: Behavioral and toxicological responses of Rhodnius prolixus and Triatoma infestans (Hemiptera: Reduviidae) to 10 monoterpene alcohols.
PubMed: Identification and field evaluation of non-host volatiles disturbing host location by the tea geometrid, Ectropis obliqua.
PubMed: Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
PubMed: Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae).
PubMed: Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
PubMed: Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea.
PubMed: Attraction modulated by spacing of pheromone components and anti-attractants in a bark beetle and a moth.
PubMed: Host resistance elicited by methyl jasmonate reduces emission of aggregation pheromones by the spruce bark beetle, Ips typographus.
PubMed: Peripheral modulation of pheromone response by inhibitory host compound in a beetle.
PubMed: Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.
PubMed: Anti-ischemic and anti-inflammatory activity of (S)-cis-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: Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
PubMed: Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
PubMed: Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
PubMed: Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics.
PubMed: Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
PubMed: Common herbs, essential oils, and monoterpenes potently modulate bone metabolism.
PubMed: Transformation of alpha-pinene using Picea abies suspension culture.
PubMed: Enhanced production of verbenol, a highly valued food flavourant, by an intergeneric fusant strain of Aspergillus niger and Penicillium digitatum.
PubMed: Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam.
PubMed: Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.
PubMed: Dose-dependent response and preliminary observations on attraction range of Ips typographus to pheromones at low release rates.
PubMed: Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
PubMed: Strategies of a bark beetle, Pityogenes bidentatus, in an olfactory landscape.
PubMed: Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
PubMed: cis-Verbenol.
PubMed: Orientation of bark beetlesPityogenes chalcographus andIps typographus to pheromonebaited puddle traps placed in grids: A new trap for control of scolytids.
PubMed: Interactions between components of the aggregation pheromone during chemotaxis by the bark beetleIps paraconfusus.
PubMed: Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
PubMed: Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
PubMed: Ipsenol: an aggregation pheromone forIps latidens (Leconte) (Coleoptera: Scolytidae).
PubMed: In vivo metabolism of the ethyl homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse.
PubMed: Identification of cis- and trans-verbenol in human urine after occupational exposure to terpenes.
PubMed: Electroantennograms by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected chiral semiochemicals.
PubMed: Secondary attraction and field activity of beetle-produced volatiles inDendroctonus terebrans.
PubMed: Olfactory orientation responses by walking femaleIps paraconfusus bark beetles I. Chemotaxis assay.
PubMed: Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse.
PubMed: Sites of production and occurrence of volatiles in Douglas-fir beetle,Dendroctonus pseudotsugae hopkins.
PubMed: In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse.
PubMed: In vivo metabolism of the n-propyl homologues of delta-8- and delta-9-tetrahydrocannabinol in the mouse.
PubMed: In vivo metabolism of the methyl homologues of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol and abn-delta-8-tetrahydrocannabinol in the mouse.
PubMed: Metabolism of (+)-trans-delta 8-tetrahydrocannabinol in the mouse in vitro and in vivo.
PubMed: Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
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: Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
PubMed: Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to their natural aggregation pheromone and its enantiomeric components.
PubMed: Sex-specific responses to aggregation pheromone Regulation of colonization density in the bark beetleIps paraconfusus.
PubMed: Alcohol dehydrogenase from the fruitfly Drosophila melanogaster. Substrate specificity of the alleloenzymes AdhS and AdhUF.
PubMed: Effect of mating on terminating aggregation during host colonization in the bark beetle,Ips paraconfusus.
PubMed: Antibiotic-induced inhibition of pheromone synthesis in a bark beetle.
PubMed: Kairomone response inThanasimus predators to pheromone components ofIps typographus.
PubMed: Interspecific effects of pheromones on the attraction of the bark beetles,Dendroctonus brevicomis andIps paraconfusus in the laboratory.
PubMed: Selective production of cis- and trans-verbenol from (-)-and (+)-alpha by a bark beetle.
PubMed: Microbiological Transformation of Terpenes: II. Transformation of alpha-Pinene.
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