Page last updated: 2024-12-06

verbenol

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Verbenol is a monoterpene alcohol found in the essential oils of various plants, including pine trees and conifers. It is a natural insect repellent and attractant, depending on the species and concentration. Verbenol is synthesized from alpha-pinene, a major component of turpentine, via a multi-step process involving oxidation and reduction. Its effects include acting as a pheromone for some insect species, influencing their behavior, and attracting or repelling them. Verbenol is studied for its potential applications in pest management and ecological research. It is a valuable tool for understanding insect communication and developing environmentally friendly methods to control pest populations.'

verbenol: RN given refers to cpd with unspecified isomeric designation; structure [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	61126
CHEBI ID	167399
SCHEMBL ID	247526
MeSH ID	M0055073

Synonyms (51)

Synonym
CHEBI:167399
473-67-6
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol
nsc6833
nsc-6833
5416-53-5
pinen-4-ol
bicyclo[3.1.1]hept-3-en-2-ol, 4,6,6-trimethyl-
d-verbenol
nsc-44159
NSC44159 ,
pinen-4-o1
NCIOPEN2_000769
(e)-verbenol
nsc-74539
nsc74539
nsc-408848
nsc408848
4,6,6-trimethylbicyclo(3.1.1)hept-3-en-2-ol
fema no. 3594
verbenol
2-pinen-4-ol
4-hydroxy-2,6,6-trimethylbicyclo(3.1.1)hept-2-ene
berbenol
bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl-
einecs 207-470-8
FT-0694070
unii-g0f32f922s
g0f32f922s ,
FT-0637761
4,7,7-trimethylbicyclo[3.1.1]hept-3-en-2-ol
SCHEMBL247526
DTXSID2042511
AKOS024365333
(1s)-(+)-cis-verbenol
J-525158
verbenzol,(1s)-(+)-cis(rg)
FT-0699814
FT-0699813
2-pinen-4-ol (8ci)
4,6,6-trimethyl-bicyclo(3.1.1)hept-3-en-2-ol
4,6,6-trimethyl-bicyclo[3.1.1]hept-3-en-2-ol
bicyclo(3.1.1)hept-3-en-2-ol, 4,6,6-trimethyl- (9ci)
4,6,6-trimethyl-bicyclo[3,1,1]hept-3-en-2-ol
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-ol, 9ci
fema 3594
(+)-verbenol
verbenols
Q2514085
mfcd00001340
F76316

Research Excerpts

Overview

Verbenol is a bicyclicbicycle secondary allylic alcohol, with pronounced camphor and mint flavor notes. It is mainly used as food flavoring.

Excerpt	Reference	Relevance
"Verbenol is a bicyclicbicycle secondary allylic alcohol, with pronounced camphor and mint flavor notes, mainly used as food flavoring. "	( Microbial oxidation of (-)-α-pinene to verbenol production by newly isolated strains. Antunes, OA; Cansian, RL; Cortina, PF; de Oliveira, D; Oestreicher, EG; Rottava, I; Toniazzo, G; Treichel, H; Zanella, CA, 2010)	2.07

Dosage Studied

Excerpt	Relevance	Reference
" Dose-response of the beetle was first examined in a trapping experiment in August 1999."	( Dose-dependent response and preliminary observations on attraction range of Ips typographus to pheromones at low release rates. Franklin, AJ; Grégoir, JC, 2001)	0.31
"3, 3, and 30 mg/d), the data suggested a positive dose-response trend."	( Southern Pine Beetle (Coleoptera: Curculionidae: Scolytinae) Pheromone Component trans-Verbenol: Enantiomeric Specificity and Potential as a Lure Adjuvant. Shepherd, WP; Sullivan, BT, 2019)	0.74

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
monoterpenoid	Any terpenoid derived from a monoterpene. The term includes compounds in which the C10 skeleton of the parent monoterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (48)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.08)	18.7374
1990's	5 (10.42)	18.2507
2000's	12 (25.00)	29.6817
2010's	23 (47.92)	24.3611
2020's	7 (14.58)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 34.82

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	34.82 (24.57)
Research Supply Index	3.89 (2.92)
Research Growth Index	5.35 (4.65)
Search Engine Demand Index	43.31 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (34.82)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.08%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	47 (97.92%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
gamma-aminobutyric acid gamma-Aminobutyric Acid: The most common inhibitory neurotransmitter in the central nervous system.. gamma-aminobutyric acid : A gamma-amino acid that is butanoic acid with the amino substituent located at C-4.	2.13	1	amino acid zwitterion; gamma-amino acid; monocarboxylic acid	human metabolite; neurotransmitter; Saccharomyces cerevisiae metabolite; signalling molecule
pyrazole 1H-pyrazole : The 1H-tautomer of pyrazole.	2	1	pyrazole
menthol Menthol: A monoterpene cyclohexanol produced from mint oils.	1.98	1	p-menthane monoterpenoid; secondary alcohol	volatile oil component
4-cresol 4-cresol: RN given refers to parent cpd. p-cresol : A cresol that consists of toluene substituted by a hydroxy group at position 4. It is a metabolite of aromatic amino acid metabolism produced by intestinal microflora in humans and animals.	2.08	1	cresol	Escherichia coli metabolite; human metabolite; uremic toxin
n-pentanol n-pentanol: RN given refers to parent cpd. pentan-1-ol : A short-chain primary fatty alcohol that is pentane in which a hydrogen of one of the methyl groups is substituted by a hydroxy group. It has been isolated from Melicope ptelefolia.	2.43	2	pentanol; short-chain primary fatty alcohol	human metabolite; plant metabolite
phencyclidine Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.	2.01	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
linalool linalool: RN given refers to parent cpd without isomeric designation; structure. linalool : A monoterpenoid that is octa-1,6-diene substituted by methyl groups at positions 3 and 7 and a hydroxy group at position 3. It has been isolated from plants like Ocimum canum.	2.47	2	monoterpenoid; tertiary alcohol	antimicrobial agent; fragrance; plant metabolite; volatile oil component
camphene camphene : A monoterpene with a bicyclic skeleton that is bicyclo[2.2.1]heptane substituted by geminal methyl groups at position 2 and a methylidene group at position 3. It is a widespread natural product found in many essential oils.	2.06	1	carbobicyclic compound; monoterpene	fragrance; plant metabolite
alpha-pinene [no description available]	5.51	20	pinene	plant metabolite
methyl benzoate methyl benzoate : A benzoate ester obtained by condensation of benzoic acid and methanol.	2.02	1	benzoate ester; methyl ester	insect attractant; metabolite
3-hydroxy-3-methylbutene 3-hydroxy-3-methylbutene: narcotic, sleep-producing principle from hops; RN given refers to parent cpd. 3-hydroxy-3-methylbut-1-ene : A tertiary alcohol that is 3-methylbut-1-ene carrying a hydroxy substituent at position 3.	2.43	2	olefinic compound; tertiary alcohol	animal metabolite; fragrance; pheromone; plant metabolite
citronellol citronellol: alcohol form of citronellal; found in rose oil; RN given refers to parent cpd without isomeric designation; structure. citronellol : A monoterpenoid that is oct-6-ene substituted by a hydroxy group at position 1 and methyl groups at positions 3 and 7.. insect repellent : An insecticide that acts as a repellent to insects.	1.98	1	monoterpenoid	plant metabolite
carvacrol carvacrol : A phenol that is a natural monoterpene derivative of cymene. An inhibitor of bacterial growth, it is used as a food additive. Potent activator of the human ion channels transient receptor potential V3 (TRPV3) and A1 (TRPA1).	1.98	1	botanical anti-fungal agent; p-menthane monoterpenoid; phenols	agrochemical; antimicrobial agent; flavouring agent; TRPA1 channel agonist; volatile oil component
myrtenol myrtenol: fragrance ingredient; structure in first source	3.51	7
beta-pinene beta-pinene: alpha-pinene is also available. beta-pinene : An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants.	2.41	2	pinene	plant metabolite
sabinene sabinene: RN given refers to cpd without isomeric designation. sabinene : A thujene that is a bicyclic monoterpene isolated from the essential oils of various plant species.	2.31	1	thujene	plant metabolite
3-carene 3-carene: RN given refers to cpd without isomeric designation	2.74	3	monoterpene
verbenone verbenone: platelet aggregation inhibitor; RN given refers to cpd without isomeric designation. 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one : A carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4.. (S)-(-)-verbenone : A 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one in which both chiral centres have S configuration.	8.77	10	carbobicyclic compound; cyclic ketone; enone
myrcene myrcene: structure in first source. beta-myrcene : A monoterpene that is octa-1,6-diene bearing methylene and methyl substituents at positions 3 and 7 respectively.	2.31	1	monoterpene	anabolic agent; anti-inflammatory agent; flavouring agent; fragrance; plant metabolite; volatile oil component
myrtenal myrtenal: RN refers to cpd without isomeric designation; structure given in first source	2.77	3
ipsdienol ipsdienol: isolated from Ips pini	7.77	3
ipsenol ipsenol: structure in first source	8.64	2
phytol [no description available]	2.11	1
brevicomin brevicomin: RN given refers to (1R-exo)-isomer; structure	2.75	3
pulegone pulegone: component of peppermint oil; RN given refers to cpd without isomeric designation; structure in Merck. (+)-pulegone : The (5R)-enantiomer of p-menth-4(8)-en-3-one.	1.98	1	p-menth-4(8)-en-3-one
spathulenol spathulenol: sesquiterpene alcohol isolated from essential oils of Artemisia vulgaris L. & Artemisia dracunculus L.. spathulenol : A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7.	2.06	1
citral citral: Xref geranial: geraniol is also available; Xref neral: nerol is also available; vitamin A antagonist; oxygenated monoterpene; inhibits cytosolic dehydrogenases; structure. citral : An enal that consists of octa-2,6-dienal bearing methyl substituents at positions 3 and 7. A mixture of the two geometric isomers geranial and neral, it is the major constituent (75-85%) of oil of lemon grass, the volatile oil of Cymbopogon citratus, or of C. flexuosus. It also occurs in oils of verbena, lemon, and orange.	1.98	1	enal; monoterpenoid; polyprenal	plant metabolite; volatile oil component
sesquiterpenes [no description available]	3	4
caryophyllene oxide caryophyllene oxide: has butyrylcholinesterase inhibitory activity; structure in first source. epoxide : Any cyclic ether in which the oxygen atom forms part of a 3-membered ring.	2.17	1	epoxide	metabolite
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.06	1
humulene humulene: structure given in first source. (1E,4E,8E)-alpha-humulene : The (1E,4E,8E)-isomer of alpha-humulene.	2.17	1	alpha-humulene
bisabolol bisabolol: monocyclic sesquiterpene alcohol with strong bacteriocidal effects, especilly against M. Tuberc.; isolated from seed plant Populus tacamacaha; RN given refers to cpd without isomeric desigation	2.06	1
jaeschkeanadiol jaeschkeanadiol: structure in first source	2.06	1	sesquiterpenoid
frontalin [no description available]	2.45	2
nad NAD(1-) : An anionic form of nicotinamide adenine dinucleotide arising from deprotonation of the two OH groups of the diphosphate moiety.	2	1	organophosphate oxoanion	cofactor; human metabolite; hydrogen acceptor; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
Arthritis, Degenerative [description not available]	2.1	1
Osteoarthritis A progressive, degenerative joint disease, the most common form of arthritis, especially in older persons. The disease is thought to result not from the aging process but from biochemical changes and biomechanical stresses affecting articular cartilage. In the foreign literature it is often called osteoarthrosis deformans.	2.1	1
Cerebral Ischemia [description not available]	2.05	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.05	1

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