ChemFOnt: Showing chemical card for (+)-Verbenone (CFc000334757)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:26:51 UTC

Chemfont ID

CFc000334757

Molecule Identification

Common Name

(+)-Verbenone

Definition

Verbenone, 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 .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Verbenone, (1S)-isomer	MeSH
Verbenone, (1R)-isomer	MeSH
Verbenone, (+-)-isomer	MeSH

Chemical Formula

C₁₀H₁₄O

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

IUPAC Name

4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one

Traditional Name

verbenone

CAS Registry Number

18309-32-5

SMILES

CC1=CC(=O)C2CC1C2(C)C

InChI Identifier

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

InChI Key

DCSCXTJOXBUFGB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Bicyclic monoterpenoid
Cyclohexenone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

cyclic ketone (CHEBI:78315 )
enone (CHEBI:78315 )
carbobicyclic compound (CHEBI:78315 )
Cyclic monoterpenes (C09913 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Herb and spice

Herb

Common verbena (FooDB: FOOD00196)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.84 g/L	ALOGPS
logP	2.3	ALOGPS
logP	2.24	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	19.84	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	45.37 m³·mol⁻¹	ChemAxon
Polarizability	17.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon