EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

verbenone
pin-2-en-4-one

Sponsors

Flavor Demo Formulas
Name:4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
CAS Number: 80-57-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:201-292-4
Nikkaji Web:J99.983K
CoE Number:11186
XlogP3-AA:1.60 (est)
Molecular Weight:150.22078000
Formula:C10 H14 O
NMR Predictor:Predict (works with chrome or firefox)
EFSA/JECFA Comments:
Racemate (EFFA, 2012g). Mixture of (+/-)-verbenone.
Category:flavor and fragrance agents
 
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
JECFA Food Flavoring:1870 verbenone
FLAVIS Number:07.196 (Old)
DG SANTE Food Flavourings:07.196 pin-2-en-4-one
FEMA Number:4216 verbenone
FDA:No longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm: VERBENONE
 
Physical Properties:
Appearance:colorless to yellow clear viscous liquid (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Specific Gravity:0.97500 to 0.98100 @ 25.00 °C.
Pounds per Gallon - (est).: 8.113 to 8.163
Refractive Index:1.49200 to 1.49800 @ 20.00 °C.
Melting Point: 43.70 °C. @ 0.00 mm Hg
Boiling Point: 103.00 to 104.00 °C. @ 16.00 mm Hg
Boiling Point: 89.00 to 90.00 °C. @ 12.00 mm Hg
Vapor Pressure:0.077000 mm/Hg @ 25.00 °C. (est)
Flash Point: 185.00 °F. TCC ( 85.00 °C. )
logP (o/w): 2.139 (est)
Soluble in:
 alcohol
 water, 943.4 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor Type: camphoreous
Odor Strength:medium
camphoreous mentholic celery
Odor Description:at 100.00 %. camphor menthol celery
Odor and/or flavor descriptions from others (if found).
Bedoukian Research
VERBENONE ≥93.0% (sum of isomers), Special Order
Odor Description:A spicy, mint, camphor note with a hint of pine, safranal type aroma
Natural, resinous, fresh, spicy, herbal notes blend well with citrus and herbaceous compositions.
Taste Description:Dry, woody
Spicy, woody, dry note for flavors like cranberry, tea.
 
Cosmetic Information:
None found
 
Suppliers:
Bedoukian Research
VERBENONE
≥93.0% (sum of isomers), Special Order
Odor: A spicy, mint, camphor note with a hint of pine, safranal type aroma
Use: Natural, resinous, fresh, spicy, herbal notes blend well with citrus and herbaceous compositions.
Flavor: Dry, woody
Spicy, woody, dry note for flavors like cranberry, tea.
BOC Sciences
For experimental / research use only.
4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one
Synerzine
Verbenone
 
Safety Information:
European information :
Most important hazard(s):
Xn - Harmful.
R 22 - Harmful if swallowed.
R 43 - May cause sensitisation by skin contact.
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)
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
Recommendation for verbenone usage levels up to:
  8.0000 % in the fragrance concentrate.
 
Maximised Survey-derived Daily Intakes (MSDI-EU): 15.00 (μg/capita/day)
Modified Theoretical Added Maximum Daily Intake (mTAMDI): 1000 (μg/person/day)
Threshold of Concern:540 (μg/person/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: 22
 average usual ppmaverage maximum ppm
baked goods: 5.0000025.00000
beverages(nonalcoholic): --
beverages(alcoholic): --
breakfast cereal: 2.0000010.00000
cheese: 3.0000015.00000
chewing gum: --
condiments / relishes: 2.0000010.00000
confectionery froastings: 4.0000020.00000
egg products: --
fats / oils: 2.0000010.00000
fish products: 1.000005.00000
frozen dairy: 3.0000015.00000
fruit ices: 3.0000015.00000
gelatins / puddings: --
granulated sugar: --
gravies: --
hard candy: 5.0000025.00000
imitation dairy: 3.0000015.00000
instant coffee / tea: --
jams / jellies: --
meat products: 1.000005.00000
milk products: 3.0000015.00000
nut products: --
other grains: --
poultry: 1.000005.00000
processed fruits: 2.0000010.00000
processed vegetables: --
reconstituted vegetables: --
seasonings / flavors: 2.0000010.00000
snack foods: --
soft candy: 5.0000025.00000
soups: 2.0000010.00000
sugar substitutes: --
sweet sauces: 2.0000010.00000
 
Food categories according to Commission Regulation EC No. 1565/2000 (EC, 2000) in FGE.06 (EFSA, 2002a). According to the Industry the "normal" use is defined as the average of reported usages and "maximum use" is defined as the 95th percentile of reported usages (EFSA, 2002i).
Note: mg/kg = 0.001/1000 = 0.000001 = 1/1000000 = ppm.
 average usage mg/kgmaximum usage mg/kg
Dairy products, excluding products of category 02.0 (01.0): 3.0000015.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0): 2.0000010.00000
Edible ices, including sherbet and sorbet (03.0): 3.0000015.00000
Processed fruit (04.1): 2.0000010.00000
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2): --
Confectionery (05.0): 4.0000020.00000
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0): 2.0000010.00000
Bakery wares (07.0): 5.0000025.00000
Meat and meat products, including poultry and game (08.0): 1.000005.00000
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0): 1.000005.00000
Eggs and egg products (10.0): --
Sweeteners, including honey (11.0): --
Salts, spices, soups, sauces, salads, protein products, etc. (12.0): 2.0000010.00000
Foodstuffs intended for particular nutritional uses (13.0): 3.0000015.00000
Non-alcoholic ("soft") beverages, excl. dairy products (14.1): --
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2): 4.0000020.00000
Ready-to-eat savouries (15.0): 5.0000025.00000
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0): 2.0000010.00000
 
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 47, Revision 1 (FGE.47Rev1): Bi- and tricyclic secondary alcohols, ketones and related esters from chemical group 8
View page or View pdf

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

EPI System: View
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):80-57-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :29025
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
Chemidplus:0000080579
 
References:
 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:80-57-9
Pubchem (cid):29025
Pubchem (sid):134992208
Pherobase:View
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2009
(IUPAC):Atomic Weights of the Elements 2009 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Everything Added to Food in the United States (EAFUS):View
CHEBI:View
KEGG (GenomeNet):C09913
HMDB (The Human Metabolome Database):Search
FooDB:FDB010452
Typical G.C.
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
RSC Learn Chemistry:View
 
Potential Blenders and core components note
For Odor
No odor group found for these
fenchone
FL/FR
laurel leaf concrete
FR
laurel leaf absolute
FL/FR
2-
methyl-3-butanone
FL/FR
yarrow oil
FL/FR
amber
amber
angelica root oil
FL/FR
balsamic
dextro-
fenchone
FL/FR
camphoreous
3-
benzylidene-2-butanone
FL/FR
bornyl isobutyrate
FL/FR
butyrophenone
FL/FR
dextro-
camphor
FL/FR
(±)-
camphor
FL/FR
camphor tree bark oil
FL/FR
beta-homo
cyclocitral
FL/FR
cyclohexanol
FL/FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
herbal ethanone
FR
hinoki leaf oil
FR
caramellic
fenugreek absolute
FL/FR
floral
hexahydrofarnesyl acetone
FL/FR
(Z)-
jasmone
FL/FR
iso
jasmone
FL/FR
2-
pentadecanone
FL/FR
green
iso
butyl benzyl carbinol
FL/FR
herbal
apium graveolens seed oil india
FL/FR
3-
butyl phthalide
FL/FR
3-
butylidene phthalide
FL/FR
celery ketone
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery undecene
FR
dimethyl cyclormol (IFF)
FR
geranic oxide
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
spike
lavender absolute
FL/FR
spike
lavender oil
FL/FR
spike
lavender oil spain
FL/FR
levisticum officinale herb oil
FL/FR
levisticum officinale root absolute
FL/FR
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
niaouli oil
FR
alpha-
pinene
FL/FR
3-
propylidene phthalide
FL/FR
rosemary absolute
FL/FR
rosemary oil egypt
FL/FR
mentholic
(±)-iso
menthone
FL/FR
spicy
iso
butyl angelate
FL/FR
galangal root oil
FL/FR
laurus nobilis leaf oil
FL/FR
laurus nobilis leaf oil turkey
FL/FR
levisticum officinale root oil
FL/FR
sugandha kokila berry oil
FR
tonka
whiskey lactone
FL/FR
woody
amber dodecane
FR
For Flavor
No flavor group found for these
3-
benzylidene-2-butanone
FL/FR
bornyl isobutyrate
FL/FR
3-
butyl phthalide
FL/FR
butyrophenone
FL/FR
cyclohexanol
FL/FR
epoxyoxophorone
FL
fenchone
FL/FR
laurus nobilis leaf oil
FL/FR
laurus nobilis leaf oil turkey
FL/FR
melaleuca leucadendron var. cajuputi leaf oil
FL/FR
3-
methyl cyclohexanone
FL
2-
methyl-3-butanone
FL/FR
yarrow oil
FL/FR
laurel leaf absolute
FL/FR
alliaceous
alliaceous
cyclopentyl mercaptan
FL
amber
iso
butyl benzyl carbinol
FL/FR
camphoreous
(±)-
camphor
FL/FR
camphor tree bark oil
FL/FR
fenchol
FL/FR
laevo-
fenchone
FL/FR
geranic oxide
FL/FR
6-
hydroxydihydrotheaspirane (mixture of isomers)
FL/FR
caramellic
fenugreek absolute
FL/FR
celery
3-
butylidene phthalide
FL/FR
cooling
beta-homo
cyclocitral
FL/FR
dextro-
fenchone
FL/FR
spike
lavender oil
FL/FR
fatty
2-
pentadecanone
FL/FR
green
angelica root oil
FL/FR
iso
butyl angelate
FL/FR
celery ketone
FL/FR
hexahydrofarnesyl acetone
FL/FR
iso
jasmone
FL/FR
3-
propylidene phthalide
FL/FR
herbal
apium graveolens seed oil india
FL/FR
celery leaf oil
FL/FR
celery seed oil CO2 extract
FL/FR
celery seed oleoresin
FL
spike
lavender absolute
FL/FR
spike
lavender oil spain
FL/FR
rosemary absolute
FL/FR
rosemary oil egypt
FL/FR
medicinal
dextro-
camphor
FL/FR
minty
(±)-iso
menthone
FL/FR
spicy
galangal root oil
FL/FR
levisticum officinale herb oil
FL/FR
levisticum officinale oleoresin
FL
levisticum officinale root absolute
FL/FR
levisticum officinale root oil
FL/FR
woody
(Z)-
jasmone
FL/FR
alpha-
pinene
FL/FR
whiskey lactone
FL/FR
 
Potential Uses:
FRfrankincense
FRgreen
FRincense
FRjuniper
FRoriental
FRraspberry
 vervain
 
Occurrence (nature, food, other):note
 apricot fruit - 3.5 mg/kg
Search Trop Picture
 artemisia diffusa krasch. ex poljak oil iran @ 13.00%
Data GC Search Trop Picture
 cabbage shoot
Search Trop Picture
 cascarilla bark oil @ 0.11%
Data GC Search Trop Picture
 cistus oil @ 0.3%
Data GC Search Trop Picture
 citrus fruits - up to 500 mg/kg
Search PMC Picture
 cornmint oil india @ 0.03%
Data GC Search Trop Picture
 cypress cone oil egypt @ 0.9%
Data GC Search Trop Picture
 echinophora cinerea oil iran @ 0.10%
Data GC Search Trop Picture
 eucalyptus globulus pseudoglobulus oil @ 0.18%
Data GC Search Trop Picture
 hinoki leaf oil @ 0.89%
Data GC Search Trop Picture
 hinoki root oil @ 2.44%
Data GC Search Trop Picture
 hinoki wood oil @ 0.29%
Data GC Search Trop Picture
 labdanum leaf oil @ 0.30%
Data GC Search Trop Picture
 labdanum oil @ 0.19%
Data GC Search Trop Picture
 laurel leaf oil turkey @ <0.10%
Data GC Search Trop Picture
 lavender oil spike spain @ 0.12%
Data GC Search Trop Picture
 lime oil CO2 extract mexico @ 0.60%
Data GC Search Trop Picture
 mango fruit - 2.7 mg/kg
Search Trop Picture
 mangrove bark red oil cuba @ trace%
Data GC Search Trop Picture
 mastic oil @ 0.12%
Data GC Search Trop Picture
 nepeta racemosa lam. oil iran @ 0.30%
Data GC Search Trop Picture
 patchouli oil china @ 0.02%
Data GC Search Trop Picture
 rosemary
Search Trop Picture
 rosemary leaf
Search Trop Picture
 rosemary oil
Search Trop Picture
 rosemary oil CO2 extract @ 8.36%
Data GC Search Trop Picture
 rosemary oil corsica @ 10.70%
Data GC Search Trop Picture
 rosemary oil egypt @ 12.33%
Data GC Search Trop Picture
 rosemary oil france @ 1.03-5.08%
Data GC Search Trop Picture
 rosemary oil morocco @ 0.00-0.46%
Data GC Search Trop Picture
 rosemary oil spain @ 6.3%
Data GC Search Trop Picture
 rosemary plant
Search Trop Picture
 rosemary shoot
Search Trop Picture
 safflower flower
Search Trop Picture
 saffron
Search Trop Picture
 spearmint oil
Search Trop Picture
 sunflower flower
Search Trop Picture
 tagete oil CO2 extract @ 0.05%
Data GC Search Trop Picture
 turpentine oil
Search Picture
 verbena oil
Search Trop Picture
 wormwood oil cuba @ 2.47%
Data GC Search Trop Picture
 wormwood oil italy @ trace%
Data GC Search Trop Picture
 yarrow oil greece @ 0.20%
Data GC Search Trop Picture
 
Synonyms:
 bicyclo(3.1.1)hept-3-en-2-one, 4,6,6-trimethyl-
 bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-
 pin-2-en-4-one
2-pinen-4-one
4,6,6-trimethyl bicyclo(3.1.1)hept-3-en-2-one
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one
 

Articles:

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, antibacterial and cytotoxic activities of the essential oil from the flowers of Tunisian Convolvulus althaeoides L.
PubMed:Asymmetric total synthesis of onoseriolide, bolivianine, and isobolivianine.
PubMed:Non-host volatile blend optimization for forest protection against the European spruce bark beetle, Ips typographus.
PubMed:Enantiomeric distribution of major chiral volatile organic compounds in juniper-flavored distillates.
PubMed:Verbenone structural analogues isolated from Artemesia aucheri as natural acaricides against Dermatophagoides spp. and Tyrophagus putrescentiae.
PubMed:Phytochemical and physical-chemical analysis of Polish willow (Salix spp.) honey: identification of the marker compounds.
PubMed:Study on Gas Chromatography-Mass Spectrometry Fingerprint of Acanthopanax brachypus.
PubMed:Coffee berry borer joins bark beetles in coffee klatch.
PubMed:Identification and field evaluation of non-host volatiles disturbing host location by the tea geometrid, Ectropis obliqua.
PubMed:Discovery of novel (1S)-(-)-verbenone derivatives with anti-oxidant and anti-ischemic effects.
PubMed:Impact of geocoding methods on associations between long-term exposure to urban air pollution and lung function.
PubMed:Interruption of the semiochemical-based attraction of ambrosia beetles to ethanol-baited traps and ethanol-injected trap trees by verbenone.
PubMed:Attractant and disruptant semiochemicals for Dendroctonus jeffreyi (Coleoptera: Curculionidae: Scolytinae).
PubMed:Population densities and tree diameter effects associated with verbenone treatments to reduce mountain pine beetle-caused mortality of lodgepole pine.
PubMed:Monoterpene derivatives from the flowers of Ferulago campestris, (Apiaceae).
PubMed:Up-regulation of astroglial heme oxygenase-1 by a synthetic (S)-verbenone derivative LMT-335 ameliorates oxygen-glucose deprivation-evoked injury in cortical neurons.
PubMed:The push-pull tactic for mitigation of mountain pine beetle (Coleoptera: Curculionidae) damage in lodgepole and whitebark pines.
PubMed:Efficacy of "Verbenone Plus" for protecting ponderosa pine trees and stands from Dendroctonus brevicomis (Coleoptera: Curculionidae) attack in British Columbia and California.
PubMed:Guatemalan potato moth Tecia solanivora distinguish odour profiles from qualitatively different potatoes Solanum tuberosum L.
PubMed:Toxicity of Zanthoxylum piperitum and Zanthoxylum armatum oil constituents and related compounds to Stomoxys calcitrans (Diptera: Muscidae).
PubMed:Investigation of effects of terpene skin penetration enhancers on stability and biological activity of lysozyme.
PubMed:Mycobacterium avium and Mycobacterium abscessus complex target distinct cystic fibrosis patient subpopulations.
PubMed:Electrophysiological and behavioural responses of Pityophthorus pubescens (Coleoptera: Scolytinae) to (E,E)-α-farnesene, (R)-(+)-limonene and (S)-(-)-verbenone in Pinus radiata (Pinaceae) stands in northern Spain.
PubMed:Chemoenzymatic synthesis of the alarm pheromone (+)-verbenone from geranyl diphosphate.
PubMed:Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C.DC in rodents.
PubMed:Electrophysiological and behavioral responses of the bark beetle Dendroctonus rhizophagus to volatiles from host pines and conspecifics.
PubMed:Efficacy of traps, lures, and repellents for Xylosandrus compactus (Coleoptera: Curculionidae) and other ambrosia beetles on Coffea arabica plantations and Acacia koa nurseries in Hawaii.
PubMed:Responses of Dendroctonus brevicomis (Coleoptera: Curculionidae) in behavioral assays: implications to development of a semiochemical-based tool for tree protection.
PubMed:Semiochemical emission from individual galleries of the southern pine beetle, (Coleoptera: Curculionidae: Scolytinae), attacking standing trees.
PubMed:Volatile organic compounds from Centaurium erythraea Rafn (Croatia) and the antimicrobial potential of its essential oil.
PubMed:Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform.
PubMed:Myrtenal inhibits acetylcholinesterase, a known Alzheimer target.
PubMed:Acaricidal effect of essential oils from Lippia graveolens (Lamiales: Verbenaceae), Rosmarinus officinalis (Lamiales: Lamiaceae), and Allium sativum (Liliales: Liliaceae) against Rhipicephalus (Boophilus) microplus (Acari: Ixodidae).
PubMed:Chromatographic methods for metabolite profiling of virus- and phytoplasma-infected plants of Echinacea purpurea.
PubMed:Survival advantages conferred to colon cancer cells by E-selectin-induced activation of the PI3K-NFκB survival axis downstream of Death receptor-3.
PubMed:Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: syntheses and applications.
PubMed:Chemotaxonomic significance of the essential oils of 18 Ferula species (Apiaceae) from Iran.
PubMed:Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves.
PubMed:Test of nonhost angiosperm volatiles and verbenone to protect trap trees for Sirex noctilio (Hymenoptera: Siricidae) from attacks by bark beetles (Coleoptera: Scolytidae) in the northeastern United States.
PubMed:Biotransformation of progesterone by cultured cells of Marchantia polymorpha.
PubMed:Antibacterial activity of the essential oil from Rosmarinus officinalis and its major components against oral pathogens.
PubMed:Control of enantioselectivity with flexible biaryl axes: terpene-based alkylzinc catalysts in enantioselective dialkylzinc additions.
PubMed:Raman optical activity: a powerful technique to investigate essential oil components.
PubMed:Rotational strength sign and normal modes description: A theoretical and experimental comparative study in bicyclic terpenes.
PubMed:Pheromone production in bark beetles.
PubMed:Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s.
PubMed:Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells.
PubMed:Efficacy of verbenone for protecting ponderosa pine stands from western pine beetle (Coleoptera: Curculionidae: Scolytinae) attack in California.
PubMed:Autoxidation versus biotransformation of alpha-pinene to flavors with Pleurotus sapidus: regioselective hydroperoxidation of alpha-pinene and stereoselective dehydrogenation of verbenol.
PubMed:Deregulation of hepatic insulin sensitivity induced by central lipid infusion in rats is mediated by nitric oxide.
PubMed:Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.
PubMed:A new family of receptor tyrosine kinases with a venus flytrap binding domain in insects and other invertebrates activated by aminoacids.
PubMed:Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.
PubMed:Improved monoterpene biotransformation with Penicillium sp. by use of a closed gas loop bioreactor.
PubMed:Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.
PubMed:Control of asymmetric biaryl conformations with terpenol moieties: syntheses, structures and energetics of new enantiopure C2-symmetric diols.
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:Tick repellent substances in the essential oil of Tanacetum vulgare.
PubMed:An enone reductase from Nicotiana tabacum: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant proteins.
PubMed:Quantitative association of bark beetles with pitch canker fungus and effects of verbenone on their semiochemical communication in Monterey pine forests in Northern Spain.
PubMed:Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.
PubMed:Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus Brevicomis LeConte (Coleoptera: Scolytidae).
PubMed:A novel porphyrin-based photocatalytic system for terpenoids production from (R)-(+)-limonene.
PubMed:Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.
PubMed:Stratified epithelium in prostatic adenocarcinoma: a mimic of high-grade prostatic intraepithelial neoplasia.
PubMed:Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).
PubMed:Nonhost angiosperm volatiles and verbenone disrupt response of western pine beetle, Dendroctonus brevicomis (Coleoptera: Scolytidae), to attractant-baited traps.
PubMed:Time-dependent density functional calculations of optical rotatory dispersion including resonance wavelengths as a potentially useful tool for determining absolute configurations of chiral molecules.
PubMed:Characterization of organic compounds in aerosol particles from a coniferous forest by GC-MS.
PubMed:A test of high-dose verbenone for stand-level protection of lodgepole and whitebark pine from mountain pine beetle (Coleoptera: Curculionidae: Scolytinae) attacks.
PubMed:Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae).
PubMed:Chemical composition and antibacterial activity of the essential oil and the gum of Pistacia lentiscus Var. chia.
PubMed:Feeding response to host and nonhost compounds by males and females of the spruce bark beetle Ips typographus in a tunneling microassay.
PubMed:Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GCxGC-TOFMS.
PubMed:Chemical composition and antimicrobial activity of Rosmarinus officinalis L. essential oil obtained via supercritical fluid extraction.
PubMed:Enhancement of attraction and trap catches of the old-house borer, Hylotrupes bajulus (Coleoptera: Cerambycidae), by combination of male sex pheromone and monoterpenes.
PubMed:Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilised Picea abies cells.
PubMed:Reconstruction of defects following bone tumor resections by distraction osteogenesis.
PubMed:Effects of 5 alpha reductase inhibitors on androgen-dependent human prostatic carcinoma cells.
PubMed:An extended use of the sentinel node in head and neck squamous cell carcinoma: results of a prospective study of 100 patients.
PubMed:Stereoselective Rh-catalyzed hydrogenation of cyclobutyl chiral enamides: double stereodifferentiation vs catalyst-controlled diastereoselection.
PubMed:The effect of selected monoterpenoids on the cellular slime mold, Dictyostelium discoideum NC4.
PubMed:chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.
PubMed:Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test.
PubMed:Synthesis of the female sex pheromone of the citrus mealybug, Planococcus citri.
PubMed:Vulgarone B, the antifungal constituent in the steam-distilled fraction of Artemisia douglasiana.
PubMed:Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography.
PubMed:High-performance liquid chromatographic method for the determination of (-)-verbenone 10-hydroxylation catalyzed by rat liver microsomes.
PubMed:Roles of human CYP2A6 and 2B6 and rat CYP2C11 and 2B1 in the 10-hydroxylation of (-)-verbenone by liver microsomes.
PubMed:[Chemical constituents in volatile oil from the flos of Dendranthema indicum var. aromaticum var. nov].
PubMed:Transformation of alpha-pinene using Picea abies suspension culture.
PubMed:Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam.
PubMed:Biotransformation of (-)-verbenone by human liver microsomes.
PubMed:Biotransformation of (-)-a-pinene by Botrytis cinerea.
PubMed:Reaction between N-alkylhydroxylamines and chiral enoate esters: more experimental evidence for a cycloaddition-like process, a rationale based on DFT theoretical calculations, and stereoselective synthesis of new enantiopure beta-amino acids.
PubMed:Preparation of Optically Active Apoverbenone and Verbenone from Nopinone by Use of the Sulfenylation-Dehydrosulfenylation Method. Stability and Reactivity Attributable to Absolute Configuration at the Sulfur Atom in Sulfoxides.
PubMed:Olfactory responses of Ips duplicatus from inner Mongolia, China to nonhost leaf and bark volatiles.
PubMed:B-cell autoepitopes on the acetylcholinesterase-homologous region of human thyroglobulin: association with Graves' disease and thyroid eye disease.
PubMed:Kairomonal response by four Monochamus species (Coleoptera: Cerambycidae) to bark beetle pheromones.
PubMed:Preparative chiral liquid chromatography for enantiomeric separation of pheromones.
PubMed:Expression of cyclooxygenase-1 and cyclooxygenase-2 in the human prostate.
PubMed:Volatile chemicals identified in extracts from leaves of Japanese mugwort (Artemisia princeps pamp.).
PubMed:Volatile components of green walnut husks.
PubMed:Divergent routes to chiral cyclobutane synthons from (-)-alpha-pinene and their use in the stereoselective synthesis of dehydro amino acids.
PubMed:Comparison of headspace techniques for sampling volatile natural products in a dynamic system.
PubMed:Bioconversion of alpha pinene to verbenone by resting cells of Aspergillus niger.
PubMed:The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems.
PubMed:The catalytic triad in Drosophila alcohol dehydrogenase: pH, temperature and molecular modelling studies.
PubMed:Influence of drug lipophilicity on terpenes as transdermal penetration enhancers.
PubMed:Strain improvement of Aspergillus sp. and Penicillium sp. by induced mutation for biotransformation of alpha-pinene to verbenol.
PubMed:Green leaf volatiles as antiaggregants for the mountain pine beetle,Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae).
PubMed:[Modification of the pharmacokinetics of some antibiotics by oral administration with an L-(-)verbenone beta-cyclodextrin complex].
PubMed:Pheromones in white pine cone beetle,Conophthorus coniperda (schwarz) (Coleoptera: Scolytidae).
PubMed:Response ofDendroctonus brevicomis Le Conte (Coleoptera: Scolytidae) to different release rates and ratios of aggregation semiochemicals and the inhibitors verbenone and ipsdienol.
PubMed:Insecticidal properties of several monoterpenoids to the house fly (Diptera: Muscidae), red flour beetle (Coleoptera: Tenebrionidae), and southern corn rootworm (Coleoptera: Chrysomelidae).
PubMed:Influence of aggregation inhibitors (verbenone and ipsidenol) on landing and attack behavior ofDendroctonus brevicomis (Coleoptera: Scolytidae).
PubMed:Repellent properties of the host compound 4-allylanisole to the southern pine beetle.
PubMed:Photoisomerization of antiaggregation pheromone verbenone: Biological and practical implications with respect to the mountain pine beetle,Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae).
PubMed:Olfactory receptor cell responses ofIps grandicollis (eichhoff) (Coleoptera: Scolytidae) to intra- and interspecific behavioral chemicals.
PubMed:Attraction of bark beetles,Tomicus piniperda,Hylurgops palliatus, andTrypodendron domesticum and other insects to short-chain alcohols and monoterpenes.
PubMed:The response of mountain pine beetle (Dendroctonus ponderosae) to lodgepole pine trees baited with verbenone and exo-brevicomin.
PubMed:The N-terminal amino acid sequence is essential for foot-and-mouth disease virus replicase activity.
PubMed:Response ofDendroctonus brevicomis andIps paraconfusus (Coleoptera: Scolytidae) to combinations of synthetic pheromone attractants and inhibitors verbenone and ipsdienol.
PubMed:Volatile compounds in the larval frass ofDendroctonus valens andDendroctonus micans (Coleoptera: Scolytidae) in relation to oviposition by the predator,Rhizophagus grandis (Coleoptera: Rhizophagidae).
PubMed:Present and future use of semiochemicals in pest management of bark beetles.
PubMed:Conversion of verbenols to verbenone by yeasts isolated fromDendroctonus ponderosae (Coleoptera: Scolytidae).
PubMed:Volatiles released from individual spruce bark beetle entrance holes Quantitative variations during the first week of attack.
PubMed:Inhibition of attraction to aggregation pheromone by verbenone and ipsenol : Density regulation mechanisms in bark beetleIps typographus.
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:Terpene alcohol pheromone production byDendroctonus ponderosae andIps paraconfusus (Coleoptera: Scolytidae) in the absence of readily culturable microorganisms.
PubMed:Antennal olfactory responsiveness of three sympatricIps species [Ips avulsus (Eichhoff),Ips calligraphus (Germar),Ips grandicollis (Eichhoff)], to intra- and interspecific behavioral chemicals.
PubMed:Oxygenated monoterpenes produced by yeasts, isolated fromIps typographus (Coleoptera: Scolytidae) and grown in phloem medium.
PubMed:Effect of verbenone on response ofDendroctonus brevicomis toexo-Brevicomin, frontalin, and myrcene.
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:[The effect of verbenone on prostaglandin production in vivo].
PubMed:[Bradykinin bronchospasm in guinea pigs: effects of indomethacin and verbenone].
PubMed:[Platelet aggregation induced by arachidonic acid, ADP, thrombin. Study of the antiaggregation effects of verbenone and indomethacin].
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:Enzymatic adaptation in ligaments during immobilization.
PubMed:Single cell responses of the Douglas-fir beetle,Dendroctonus pseudotsugae hopkins (Coleoptera: Scolytidae), to pheromones and host odors.
PubMed:Response of the clerid predatorThanasimus dubius (F.) to bark beetle pheromones and tree volatiles in a wind tunnel.
PubMed:Antennal olfactory responsiveness of Douglas-fir beetle,Dendroctonus pseudotsugae Hopkins (Coleoptera: Scolytidae) to pheromones and host odors.
PubMed:Sensitivity of antennae of male and femaleIps paraconfusus (Coleoptera: Scolytidae) to its pheromone and other behavior-modifying chemicals.
PubMed:Drosophila melanogaster alcohol dehydrogenase: an electrophoretic study of the AdhS, AdhF, and AdhUF alleloenzymes.
PubMed:Interruption of response ofDendroctonus brevicomis to its attractive pheromone by components of the pheromone.
PubMed:Interspecific effects of pheromones on the attraction of the bark beetles,Dendroctonus brevicomis andIps paraconfusus in the laboratory.
PubMed:[Biogenetic relations between verbenone and alpha-pinene in Rosmarinus officinalis L].
PubMed:Microbiological Transformation of Terpenes: II. Transformation of alpha-Pinene.
 
Notes:
platelet aggregation inhibitor.
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