ChemFOnt: Showing chemical card for cis-2-Carveol (CFc000333605)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:51 UTC

Chemfont ID

CFc000333605

Molecule Identification

Common Name

cis-2-Carveol

Definition

(-)-cis-carveol, also known as cis-P-mentha-6,8-dien-2-ol, 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. Thus, (-)-cis-carveol is considered to be an isoprenoid lipid molecule (-)-cis-carveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-cis-carveol is a spearmint tasting compound found in citrus, which makes (-)-cis-carveol a potential biomarker for the consumption of this food product.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(-)-(4R,6R)-cis-Carveol	ChEBI
(-)-cis-P-Mentha-1,8-dien-6-ol	HMDB
(1R)-cis-Carveol	HMDB
(1R,5R)-(-)-cis-Carveol	HMDB
(1R-cis)-2-Methyl-5-(1-methylvinyl)cyclohex-2-en-1-ol	HMDB
(1R-cis)-2-Methyl-5-isopropenyl-2-cyclohexen-1-ol	HMDB
(4R,6R)-P-Mentha-1,8-dien-6-ol	HMDB
2-Methyl-5-(1-methylethenyl)-(1R,5R)-2-cyclohexen-1-ol	HMDB
2-Methyl-5-(1-methylethenyl)-(1R-cis)-2-cyclohexen-1-ol	HMDB
cis-(-)-Carveol	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

IUPAC Name

(1R,5R)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-en-1-ol

Traditional Name

(-)-cis-carveol

CAS Registry Number

2102-59-2

SMILES

CC(=C)[C@@H]1CC=C(C)[C@H](O)C1

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)10(11)6-9/h4,9-11H,1,5-6H2,2-3H3/t9-,10-/m1/s1

InChI Key

BAVONGHXFVOKBV-NXEZZACHSA-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
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

carveol (CHEBI:227 )
Menthane monoterpenoids (C11395 )
Cyclic monoterpenes (C11395 )
Menthane monoterpenoids (LMPR0102090030 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036082)

Source

Endogenous

Endogenous (HMDB: HMDB0036082)

Plant

Plant (HMDB: HMDB0036082)

Animal

Animal (HMDB: HMDB0036082)

Exogenous

Food

Food (HMDB: HMDB0036082)

Herb and spice

Spice

Caraway (FooDB: FOOD00043)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036082)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036082)

Lipid metabolism pathway (HMDB: HMDB0036082)

Cellular process

Cell signaling (HMDB: HMDB0036082)

Biochemical process

Lipid transport (HMDB: HMDB0036082)

Role

Biological role

Energy source (HMDB: HMDB0036082)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036082)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0036082)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.82 g/L	ALOGPS
logP	2.41	ALOGPS
logP	1.99	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	18.21	ChemAxon
pKa (Strongest Basic)	-1.4	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	48 m³·mol⁻¹	ChemAxon
Polarizability	18.39 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