ChemFOnt: Showing chemical card for Dihydroneocarveol (CFc000333330)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:18 UTC

Chemfont ID

CFc000333330

Molecule Identification

Common Name

Dihydroneocarveol

Definition

Dihydrocarveol, also known as 2-methyl-5-(1-methylethenyl)cyclohexanol or 6-methyl-3-isopropenylcyclohexanol, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Dihydrocarveol is a herbal, menthol, and minty tasting compound and can be found in a number of food items such as spearmint, dill, pot marjoram, and pepper (spice), which makes dihydrocarveol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,6-Dihydrocarveol	ChEBI
2-Methyl-5-(1-methylethenyl)cyclohexanol	ChEBI
2-Methyl-5-isopropenylcyclohexanol	ChEBI
5-Isopropenyl-2-methylcyclohexanol	ChEBI
6-Methyl-3-isopropenylcyclohexanol	ChEBI
8-p-Menthen-2-ol	ChEBI
Menth-8-en-2-ol	ChEBI
2-Methyl-5-(1-methylvinyl)cyclohexan-1-ol	MeSH
a Dihydrocarveol	ChEBI

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

IUPAC Name

2-methyl-5-(prop-1-en-2-yl)cyclohexan-1-ol

Traditional Name

dihydrocarveol

CAS Registry Number

619-01-2

SMILES

CC1CCC(CC1O)C(C)=C

InChI Identifier

InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)10(11)6-9/h8-11H,1,4-6H2,2-3H3

InChI Key

KRCZYMFUWVJCLI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexanol
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:50215 )
p-menthane monoterpenoid (CHEBI:50215 )
a dihydrocarveol (CPD-10034 )

Functional Ontology

Not Available

Exogenous (FooDB: )

Food

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.32 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.32	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	18.99	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.22 m³·mol⁻¹	ChemAxon
Polarizability	19.02 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon