Record Information
Version1.0
Creation date2010-04-08 22:07:37 UTC
Update date2019-11-26 03:01:39 UTC
Primary IDFDB007471
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name(+)-Verbenone
DescriptionVerbenone, also known as verbenone, (1r)-isomer, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Verbenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Verbenone is a camphor, celery, and menthol tasting compound and can be found in a number of food items such as sunflower, cabbage, spearmint, and safflower, which makes verbenone a potential biomarker for the consumption of these food products. Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle .
CAS Number18309-32-5
Structure
Thumb
Synonyms
SynonymSource
(-)-verbenonebiospider
(1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-onebiospider
(1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-ene-2-onebiospider
(1R-cis)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-ene-2-onebiospider
(1R)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-en-2-onebiospider
(1S,5S)-2-Pinen-4-onebiospider
(1S,5S)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-onebiospider
(1S)-(-)-Verbenonebiospider
(r)-(+)-verbenonebiospider
2-Pinen-4-one, (1R,5R)-(+)-biospider
4,6,6-Trimethyl-(1R)-bicyclohept-3-en-2-onebiospider
Bicyclo(3.1.1)hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-biospider
Bicyclo(3.1.1)hept-3-en-2-one, 4,6,6-trimethyl-, (1R,5R)-biospider
Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-biospider
Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-biospider
Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-biospider
Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-biospider
D-verbenonebiospider
DL-verbenonebiospider
L-verbenonebiospider
Verbenone (d,l-)biospider
Verbenone (van)biospider
Verbenone, (+)-biospider
Verbenone,(d)biospider
Verbenone,(DL)biospider
Verbenone,(l)biospider
Verbinonebiospider
Predicted PropertiesNot Available
Chemical FormulaC10H14O
IUPAC name
InChI IdentifierInChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3
InChI KeyDCSCXTJOXBUFGB-UHFFFAOYSA-N
Isomeric SMILESCC1=CC(=O)C2CC1C2(C)C
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
Classification
ClassificationNot classified
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointBoiling Pt : 227.5 oC
Experimental Water SolubilityNot Available
Experimental logP2.23GRIFFIN,S ET AL. (1999)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID29025
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke ID(+)-VERBENONE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).