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verbenol

Chemical Structure

General Material Information

Preferred name verbenol
Trivial Name Verbenol
Short Description pin-2-en-4-ol
Formula C10 H16 O
CAS Number 473-67-6
FEMA Number 3594
Flavis Number 2.101
ECHA Number 207-470-8
FDA UNII G0F32F922S
Nikkaji Number J5.958G
COE Number 10304
xLogP3-AA 1.60 (est)
Bio Activity Summary External link
NMR Predictor External link
JECFA Food Flavoring 1404 verbenol
FDA Patent No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm 473-67-6 ; VERBENOL
Synonyms
  • bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-
  • bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-
  • 4-hydroxy-2,6,6-trimethyl bicyclo(3.1.1)hept-2-ene
  • 4-hydroxy-2,6,6-trimethylbicyclo(3.1.1)hept-2-ene
  • pin-2-en-4-ol
  • 2-pinen-4-ol
  • trimethyl bicyclo-3-hepten-2-ol
  • 4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-ol
  • trimethylbicyclo-3-hepten-2-ol
  • 4,6,6-trimethylbicyclo(3.1.1)hept-3-en-2-ol
  • 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
  • D- verbenol
  • dextro- verbenol
  • 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
  • 2-Pinen-4-ol
  • NSC 408848
  • 2,6,6-Trimethylbicyclo[3.1.1]hept-2-en-4-ol

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

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Literature & References

4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:473-67-6
Pubchem (cid):61126
Pubchem (sid):135017717
Publications by PubMed
Electrophysiological and behavioural responses of the tea geometrid Ectropis obliqua (Lepidoptera: Geometridae) to volatiles from a non-host plant, rosemary, Rosmarinus officinalis (Lamiaceae).
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.
Anti-inflammatory and chondroprotective activity of (+)-α-pinene: structural and enantiomeric selectivity.
Chemical similarity between historical and novel host plants promotes range and host expansion of the mountain pine beetle in a naïve host ecosystem.
GABA(A) receptor modulation by terpenoids from Sideritis extracts.
Behavioral and toxicological responses of Rhodnius prolixus and Triatoma infestans (Hemiptera: Reduviidae) to 10 monoterpene alcohols.
Identification and field evaluation of non-host volatiles disturbing host location by the tea geometrid, Ectropis obliqua.
Volatile oil of Artemisia santolina decreased morphine withdrawal jumping in mice.
Faecal chemical cues in water buffalo that facilitate estrus detection.
Insecticide activity of essential oils of Mentha longifolia, Pulicaria gnaphalodes and Achillea wilhelmsii against two stored product pests, the flour beetle, Tribolium castaneum, and the cowpea weevil, Callosobruchus maculatus.
Bioactivities of volatile components from Nepalese Artemisia species.
Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
Role of ipsdienol, ipsenol, and cis-verbenol in chemical ecology of Ips avulsus, Ips calligraphus, and Ips grandicollis (Coleoptera: Curculionidae: Scolytinae).
Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
Semiochemical emission from individual galleries of the southern pine beetle, (Coleoptera: Curculionidae: Scolytinae), attacking standing trees.
Chemical composition and antioxidant activity of the essential oil of Juniperus phoenicea L. berries.
Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea.
Mutual interactions between an invasive bark beetle and its associated fungi.
Attraction modulated by spacing of pheromone components and anti-attractants in a bark beetle and a moth.
Host resistance elicited by methyl jasmonate reduces emission of aggregation pheromones by the spruce bark beetle, Ips typographus.
Composition and antifungal activity of the essential oil from the rhizome and roots of Ferula hermonis.
Peripheral modulation of pheromone response by inhibitory host compound in a beetle.
Pheromone production in bark beetles.
Autoxidation of alpha-pinene at high oxygen pressure.
Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.
Microbial oxidation of (-)-α-pinene to verbenol production by newly isolated strains.
Functional genomics of mountain pine beetle (Dendroctonus ponderosae) midguts and fat bodies.
Anti-ischemic and anti-inflammatory activity of (S)-cis-verbenol.
Autoxidation versus biotransformation of alpha-pinene to flavors with Pleurotus sapidus: regioselective hydroperoxidation of alpha-pinene and stereoselective dehydrogenation of verbenol.
Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
Electrophysiological and behavioral responses of Dendroctonus valens (Coleoptera: Curculionidae: Scolytinae) to four bark beetle pheromones.
P450(BM-3)-catalyzed whole-cell biotransformation of alpha-pinene with recombinant Escherichia coli in an aqueous-organic two-phase system.
Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
Sensitive determination of monoterpene alcohols in urine by HPLC-FLD combined with ESI-MS detection after online-solid phase extraction of the monoterpene-coumarincarbamate derivates.
Synergistic blends of monoterpenes for aggregation pheromones of the mountain pine beetle (Coleoptera: Curculionidae).
Anchoring effects in a wide binding pocket: the molecular basis of regioselectivity in engineered cytochrome P450 monooxygenase from B. megaterium.
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.
Tick repellent substances in the essential oil of Tanacetum vulgare.
Improvement of P450(BM-3) whole-cell biocatalysis by integrating heterologous cofactor regeneration combining glucose facilitator and dehydrogenase in E. coli.
High individual variation in pheromone production by tree-killing bark beetles (Coleoptera: Curculionidae: Scolytinae).
Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
Chemical composition and antifungal activity of the essential oils of three species of Artemisia on some soil-borne phytopathogens.
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.
Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics.
Analysis of the essential oil composition of eight Anthemis species from Greece.
Olfactory receptor neurons in two Heliothine moth species responding selectively to aliphatic green leaf volatiles, aromatic compounds, monoterpenes and sesquiterpenes of plant origin.
Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilised Picea abies cells.
Repellency of essential oils of some Kenyan plants against Anopheles gambiae.
Chemical composition and antimicrobial activity of the essential oils from the gum of Turkish pistachio (Pistacia vera L.).
Exposure assessment of monoterpenes and styrene: a comparison of air sampling and biomonitoring.
Electroantennogram responses of Douglas-fir seed chalcids to plant volatiles.
Production of verbenol, a high valued food flavourant from a fusant strain of Aspergillus niger.
Common herbs, essential oils, and monoterpenes potently modulate bone metabolism.
Transformation of alpha-pinene using Picea abies suspension culture.
Enhanced production of verbenol, a highly valued food flavourant, by an intergeneric fusant strain of Aspergillus niger and Penicillium digitatum.
Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam.
Sensitive biomonitoring of monoterpene exposure by gas chromatographic-mass spectrometric measurement of hydroxy terpenes in urine.
[Study on chemical constituents of Dendranthema morifolium by GC-MS].
Dose-dependent response and preliminary observations on attraction range of Ips typographus to pheromones at low release rates.
Monoterpene and wood dust exposures: work-related symptoms among Finnish sawmill workers.
Composition and antimicrobial activity of the essential oils of Micromeria cristata subsp. phrygia and the enantiomeric distribution of borneol.
Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
Strategies of a bark beetle, Pityogenes bidentatus, in an olfactory landscape.
Chiral recognition between a substituted cyclooctatetraene dianion and a half crown ether substituted with ibuprofen.
Volatile components of green walnut husks.
Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
cis-Verbenol.
The catalytic triad in Drosophila alcohol dehydrogenase: pH, temperature and molecular modelling studies.
Strain improvement of Aspergillus sp. and Penicillium sp. by induced mutation for biotransformation of alpha-pinene to verbenol.
Pheromones in white pine cone beetle,Conophthorus coniperda (schwarz) (Coleoptera: Scolytidae).
Insecticidal properties of several monoterpenoids to the house fly (Diptera: Muscidae), red flour beetle (Coleoptera: Tenebrionidae), and southern corn rootworm (Coleoptera: Chrysomelidae).
Orientation of bark beetlesPityogenes chalcographus andIps typographus to pheromonebaited puddle traps placed in grids: A new trap for control of scolytids.
Role of chirality in olfactory-directed behavior: Aggregation of pine engraver beetles in the genusIps (Coleoptera: Scolytidae).
Interactions between components of the aggregation pheromone during chemotaxis by the bark beetleIps paraconfusus.
Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
Floral volatiles ofTanacetum vulgare L. attractive toLobesia botrana den. et schiff. females.
Renal elimination of verbenols in man following experimental alpha-pinene inhalation exposure.
Ipsenol: an aggregation pheromone forIps latidens (Leconte) (Coleoptera: Scolytidae).
In vivo metabolism of the ethyl homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse.
Conversion of verbenols to verbenone by yeasts isolated fromDendroctonus ponderosae (Coleoptera: Scolytidae).
Identification of cis- and trans-verbenol in human urine after occupational exposure to terpenes.
Volatiles released from individual spruce bark beetle entrance holes Quantitative variations during the first week of attack.
Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus.
Electroantennograms by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected chiral semiochemicals.
Secondary attraction and field activity of beetle-produced volatiles inDendroctonus terebrans.
Variation of enantiomeric composition of α-pinene in norway spruce,Picea abies, and its influence on production of verbenol isomers byIps typographus in the field.
Olfactory orientation responses by walking femaleIps paraconfusus bark beetles I. Chemotaxis assay.
Individual variation in aggregation pheromone content of the bark beetle,Ips typographus.
Metabolism of n-hexyl-homologues of delta-8-tetrahydrocannabinol and delta-9-tetrahydrocannabinol in the mouse.
Sites of production and occurrence of volatiles in Douglas-fir beetle,Dendroctonus pseudotsugae hopkins.
Antennal olfactory responsiveness of three sympatricIps species [Ips avulsus (Eichhoff),Ips calligraphus (Germar),Ips grandicollis (Eichhoff)], to intra- and interspecific behavioral chemicals.
In vivo metabolism of the n-butyl-homologues of delta 9-tetrahydrocannabinol and delta 8-tetrahydrocannabinol by the mouse.
In vivo metabolism of the n-propyl homologues of delta-8- and delta-9-tetrahydrocannabinol in the mouse.
In vivo metabolism of the methyl homologues of delta-8-tetrahydrocannabinol, delta-9-tetrahydrocannabinol and abn-delta-8-tetrahydrocannabinol in the mouse.
Partial inhibition of pheromone production inDendroctonus ponderosae (Coleoptera: Scolytidae) by polysubstrate monooxygenase inhibitors.
Oxygenated monoterpenes produced by yeasts, isolated fromIps typographus (Coleoptera: Scolytidae) and grown in phloem medium.
Response of mountain pine beetle,Dendroctonus ponderosae Hopkins, and pine engraver,Ips pint (SAY), to ipsdienol in southwestern British Columbia.
Metabolism of (+)-trans-delta 8-tetrahydrocannabinol in the mouse in vitro and in vivo.
Attraction to pheromone sources of different quantity, quality, and spacing: Density-regulation mechanisms in bark beetleIps typographus.
Differences in attraction to semiochemicals present in sympatric pine shoot beetles,Tomicus minor andT. piniperda.
Semiochemicals produced by western balsam bark beetle,Dryocoetes confusus Swaine (Coleoptera: Scolytidae).
Field response of spruce bark beetle,Ips typographus, to aggregation pheromone candidates.
Electroantennogram responses by mountain pine beetles,Dendroctonus ponderosae Hopkins, exposed to selected semiochemicals.
Interconversion of verbenols and verbenone by identified yeasts isolated from the spruce bark beetleIps typographus.
Quantitative variation of pheromone components in the spruce bark beetleIps typographus from different attack phases.
Attractive and inhibitory pheromones produced in the bark beetle,Dendroctonus brevicomis, during host colonization: Regulation of inter- and intraspecific competition.
Single cell responses of the Douglas-fir beetle,Dendroctonus pseudotsugae hopkins (Coleoptera: Scolytidae), to pheromones and host odors.
Pheromone production by axenically rearedDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae).
Response of the clerid predatorThanasimus dubius (F.) to bark beetle pheromones and tree volatiles in a wind tunnel.
Antennal olfactory responsiveness of Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae) to pheromones and host odors.
Bark beetle conversion of a plant compound to a sex-specific inhibitor of pheromone attraction.
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to their natural aggregation pheromone and its enantiomeric components.
Sex-specific responses to aggregation pheromone Regulation of colonization density in the bark beetleIps paraconfusus.
Frontalin in the male mountain pine beetle.
Alcohol dehydrogenase from the fruitfly Drosophila melanogaster. Substrate specificity of the alleloenzymes AdhS and AdhUF.
Field bioassay ofexo- andendo-brevicomin withDendroctonus ponderosae in lodgepole pine.
Seasonal variation in laboratory response to behavioral chemicals of the southern pine beetle.
Effect of mating on terminating aggregation during host colonization in the bark beetle,Ips paraconfusus.
Antibiotic-induced inhibition of pheromone synthesis in a bark beetle.
Terpenoids biotransformation in mammals III: Biotransformation of alpha-pinene, beta-pinene, pinane, 3-carene, carane, myrcene, and p-cymene in rabbits.
Kairomone response inThanasimus predators to pheromone components ofIps typographus.
Interspecific effects of pheromones on the attraction of the bark beetles,Dendroctonus brevicomis andIps paraconfusus in the laboratory.
Metabolism of alpha- and beta-pinene, p-cymene and 1,8-cineole in the brushtail possum, Trichosurus vulpecula.
Selective production of cis- and trans-verbenol from (-)-and (+)-alpha by a bark beetle.
Production of verbenol pheromone by a bacterium isolated from bark beetles.
Sound production in scolytidae:chemostimulus of sonic signal by the douglas-fir beetle.
Microbiological Transformation of Terpenes: II. Transformation of alpha-Pinene.

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
FDA Substances Added to Food (formerly EAFUS):View
HMDB (The Human Metabolome Database):HMDB36129
FooDB:FDB014977
Export Tariff Code:2906.19.5000
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

PhysChem Properties

Material listed in food chemical codex No
Molecular weight 152.23672485352
Melting Point 63 to 67°C @ 760 mm Hg
Boiling Point 214 to 215°C @ 760 mm Hg
Acid Value 1 max KOH/g
Vapor Pressure 0.033 mmHg @ 25 °C
Flash Point TCC Value 85 °C TCC
logP (o/w) 2.554 est
Solubility
alcohol Yes
water, very slightly Yes
water, 480.4 mg/L @ 25 °C (est) Yes
water No

Organoleptic Properties

Odor Type: Balsamic
fresh, pine, ozone, herbal
Odor strength medium
Substantivity > 168 hour(s) at 100.00 %
General comment At 100.00 %. fresh pine ozone
Flavor Type: Herbal
herbal, pine
General comment Herbal pine
For an herbaceous pine note in flavor blends. Herbal

Occurrences

Potential Uses

Applications
Odor purposes Herbal , Incense , Lavender spike lavender , Pine , Rosemary
Flavoring purposes Lavender spike lavender
Other purposes Ozone
Cosmetic purposes Perfuming agents

Safety Information

Safety information

Preferred SDS: View
European information :
Most important hazard(s):
Xi - Irritant
R 38 - Irritating to skin.
S 02 - Keep out of the reach of children.
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)
None found.
GHS Label elements, including precautionary statements
Pictogram
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
intraperitoneal-mouse LDLo 125 mg/kg
"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 7, Pg. 794, 1955.

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
Recommendation for verbenol usage levels up to:
3.0000 % in the fragrance concentrate.
Maximised Survey-derived Daily Intakes (MSDI-EU): 0.012 (μg/capita/day)
Maximised Survey-derived Daily Intakes (MSDI-USA): 0.20 (μg/capita/day)
Threshold of Concern:1800 (μg/person/day)
Structure Class: I
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: 11
Click here to view publication 11
average usual ppmaverage maximum ppm
baked goods: -1.00000
beverages(nonalcoholic): -1.00000
beverages(alcoholic): --
breakfast cereal: --
cheese: --
chewing gum: --
condiments / relishes: --
confectionery froastings: --
egg products: --
fats / oils: --
fish products: --
frozen dairy: -1.00000
fruit ices: --
gelatins / puddings: -1.00000
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: -1.00000
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 212: alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 212 Revision 1 (FGE.212Rev1): alpha,beta-Unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19.
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87 Revision 1 (FGE.87Rev1): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 87, Revision 2 (FGE.87Rev2): Consideration of bicyclic secondary alcohols, ketones and related esters evaluated by JECFA (63rd meeting) structurally related to bicyclic secondary alcohols, ketones and related esters evaluated by EFSA in FGE.47Rev1 (2008)
View page or View pdf

Scientific Opinion on Flavouring Group Evaluation 212 Revision 3 (FGE.212Rev3): a,ß-unsaturated alicyclic ketones and precursors from chemical subgroup 2.6 of FGE.19
View page or View pdf

EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):473-67-6
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :61126
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:2
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
Chemidplus:0000473676