VERBENONE, (+)-

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H14O
Molecular Weight	150.2176
Optical Activity	( + )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC(=O)[C@@H]2C[C@H]1C2(C)C

InChI

InChIKey=DCSCXTJOXBUFGB-SFYZADRCSA-N

InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3/t7-,8+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C10H14O
Molecular Weight	150.2176
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Biotransformation of progesterone by cultured cells of Marchantia polymorpha.	2010-12-09	21138062
Antibacterial activity of the essential oil from Rosmarinus officinalis and its major components against oral pathogens.	2010-12-09	21138060
Control of enantioselectivity with flexible biaryl axes: terpene-based alkylzinc catalysts in enantioselective dialkylzinc additions.	2010-12-03	20927784
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.	2010-12	21309230
Measurement of secondary products during oxidation reactions of terpenes and ozone based on the PTR-MS analysis: effects of coexistent carbonyl compounds.	2010-11	21139865
Genetics, phosphorus availability, and herbivore-derived induction as sources of phenotypic variation of leaf volatile terpenes in a pine species.	2010-10	20952630
Pheromone production in bark beetles.	2010-10	20727970
Raman optical activity: a powerful technique to investigate essential oil components.	2010-09	20923000
Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal.	2010-06-10	20548795
Quantitative variation and biosynthesis of hindgut volatiles associated with the red turpentine beetle, Dendroctonus valens LeConte, at different attack phases.	2010-06	19671207
Activated glutathione metabolism participates in protective effects of carnosic acid against oxidative stress in neuronal HT22 cells.	2010-05	19941258
Investigation of the volatile fraction of rosemary infusion extracts.	2010-04-29	21179360
Constituents of the essential oil of Suregada zanzibariensis leaves are repellent to the mosquito, Anopheles gambiae s.s.	2010	20569134
Autoxidation versus biotransformation of alpha-pinene to flavors with Pleurotus sapidus: regioselective hydroperoxidation of alpha-pinene and stereoselective dehydrogenation of verbenol.	2009-11-11	19817425
Efficacy of verbenone for protecting ponderosa pine stands from western pine beetle (Coleoptera: Curculionidae: Scolytinae) attack in California.	2009-10	19886449
Improved monoterpene biotransformation with Penicillium sp. by use of a closed gas loop bioreactor.	2009-06	19322596
Specificity and redundancy in the olfactory system of the bark beetle Ips typographus: single-cell responses to ecologically relevant odors.	2009-06	19233334
Aggregation pheromone of the Qinghai spruce bark beetle, Ips nitidus eggers.	2009-05	19408044
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.	2008-02	18348798
An enone reductase from Nicotiana tabacum: cDNA cloning, expression in Escherichia coli, and reduction of enones with the recombinant proteins.	2008-02	17945329
Tick repellent substances in the essential oil of Tanacetum vulgare.	2008-01	18283947
2-[(1S,3S)-3-Acetyl-2,2-dimethyl-cyclo-butyl]-N-(m-tol-yl)acetamide.	2007-12-18	21200856
Cross-attraction between an exotic and a native pine bark beetle: a novel invasion mechanism?	2007-12-12	18074026
Quantitative association of bark beetles with pitch canker fungus and effects of verbenone on their semiochemical communication in Monterey pine forests in Northern Spain.	2007-08	17716465
Electrophysiological and behavioral responses of Ips duplicatus to aggregation pheromone in Inner Mongolia, China: amitinol as a potential pheromone component.	2007-07	17558535
Acetophenone as an anti-attractant for the western pine beetle, Dendroctonus Brevicomis LeConte (Coleoptera: Scolytidae).	2007-04	17318432
Electrophysiological and behavioral responses of Ips subelongatus to semiochemicals from its hosts, non-hosts, and conspecifics in China.	2007-02	17216361
Characterization of organic compounds in aerosol particles from a coniferous forest by GC-MS.	2006-08	16434076
Acaricidal activities of paeonol and benzoic acid from Paeonia suffruticosa root bark and monoterpenoids against Tyrophagus putrescentiae (Acari: Acaridae).	2006-06	16602084
Time-dependent density functional calculations of optical rotatory dispersion including resonance wavelengths as a potentially useful tool for determining absolute configurations of chiral molecules.	2006-02-23	16480306
Nonhost angiosperm volatiles and verbenone disrupt response of western pine beetle, Dendroctonus brevicomis (Coleoptera: Scolytidae), to attractant-baited traps.	2005-12	16539131
Vapor phase toxicity of marjoram oil compounds and their related monoterpenoids to Blattella germanica (Orthoptera: Blattellidae).	2005-10-05	16190647
Chemical composition and antibacterial activity of the essential oil and the gum of Pistacia lentiscus Var. chia.	2005-10-05	16190616
A test of high-dose verbenone for stand-level protection of lodgepole and whitebark pine from mountain pine beetle (Coleoptera: Curculionidae: Scolytinae) attacks.	2005-10	16334331
Enhancement of attraction and trap catches of the old-house borer, Hylotrupes bajulus (Coleoptera: Cerambycidae), by combination of male sex pheromone and monoterpenes.	2005-07	15776406
Analysis of volatile components from Ziziphora taurica subsp. taurica by steam distillation, superheated-water extraction, and direct thermal desorption with GCxGC-TOFMS.	2005-05	15900460
Feeding response to host and nonhost compounds by males and females of the spruce bark beetle Ips typographus in a tunneling microassay.	2005-04	16124249
Chemical composition and antimicrobial activity of Rosmarinus officinalis L. essential oil obtained via supercritical fluid extraction.	2005-04	15830672
Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilised Picea abies cells.	2005-02	15725657
Stereoselective Rh-catalyzed hydrogenation of cyclobutyl chiral enamides: double stereodifferentiation vs catalyst-controlled diastereoselection.	2004-11-12	15527278
chemical composition, plant genetic differences, antimicrobial and antifungal activity investigation of the essential oil of Rosmarinus officinalis L.	2004-06-02	15161226
Antinociceptive effects of the essential oil of Dracocephalum kotschyi in the mouse writhing test.	2004-04-20	15144738
High-performance liquid chromatographic method for the determination of (-)-verbenone 10-hydroxylation catalyzed by rat liver microsomes.	2003-08-15	12906903
Vulgarone B, the antifungal constituent in the steam-distilled fraction of Artemisia douglasiana.	2003-08	12956506
Roles of human CYP2A6 and 2B6 and rat CYP2C11 and 2B1 in the 10-hydroxylation of (-)-verbenone by liver microsomes.	2003-08	12867494
Assessing the separation of neutral plant secondary metabolites by micellar electrokinetic chromatography.	2003-07-04	12929969
Transformation of alpha-pinene using Picea abies suspension culture.	2003-03	12662089
Molecular recognition in (+)-alpha-pinene oxidation by cytochrome P450cam.	2003-01-22	12526670
Biotransformation of (-)-verbenone by human liver microsomes.	2002-11	12506987
[Chemical constituents in volatile oil from the flos of Dendranthema indicum var. aromaticum var. nov].	2002-08	12776497

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:35:48 GMT 2025` Edited by `admin` on `Mon Mar 31 19:35:48 GMT 2025`
Record UNII	99S17893UW
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VERBENONE, (+)-

Common Name

English

(+)-.ALPHA.-VERBENONE

Preferred Name

English

NSC-36846

Code

English

D-VERBENONE [MI]

Common Name

English

2-PINEN-4-ONE, (1R,5R)-(+)-

Common Name

English

(1R,5R)-VERBENONE

Common Name

English

BICYCLO(3.1.1)HEPT-3-EN-2-ONE, 4,6,6-TRIMETHYL-, (1R)-

Systematic Name

English

(+)-VERBENONE

Common Name

English

(R)-(+)-VERBENONE

Common Name

English

BICYCLO(3.1.1)HEPT-3-EN-2-ONE, 4,6,6-TRIMETHYL-, (1R,5R)-

Systematic Name

English

(1R)-(+)-VERBENONE

Common Name

English

(R)-(+)-.ALPHA.-VERBENONE

Common Name

English

Classification Tree Code System Code

EPA PESTICIDE CODE

128986