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(E)-verbenol

flavor and fragrance agents
2D:
3D:
CAS Number: 1820-09-3
ECHA EC Number: 217-335-5
FDA UNII: 5E8197JSI1
Category: flavor and fragrance agents
IUPAC Name: (E)-verbenol
InChI : InChI=1/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9+/m1/s1
Std.InChI: InChI=1S/C10H16O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-9,11H,5H2,1-3H3/t7-,8+,9+/m1/s1
InChIKey : WONIGEXYPVIKFS-VGMNWLOBBJ
Std.InChIKey: WONIGEXYPVIKFS-VGMNWLOBSA-N
SMILES : CC1=C[C@@H]([C@@H]2C[C@H]1C2(C)C)O
MDL: MFCD00798105
Molar Refractivity : 45.55 ± 0.3 cm3 (est)
Parachor : 362.5 ± 6.0 cm3 (est)
Index of Refraction : 1.511 ± 0.02 (est)
Surface Tension : 32.4 ± 3.0 dyne/cm (est)
Density : 1.002 ± 0.06 g/cm3 (est)
Polarizability : 18.05 ± 0.5 10-24cm3 (est)

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

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

Cosmetic Information:

None found

Suppliers:

None found

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

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

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

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

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

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

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

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

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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