ChemFOnt: Showing chemical card for Dihydroisocarveol (CFc000281778)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-14 03:33:30 UTC

Chemfont ID

CFc000281778

Molecule Identification

Common Name

Dihydroisocarveol

Definition

(-)-dihydrocarveol, also known as (1r,2r,5r)-5-isopropenyl-2-methylcyclohexanol or (1r,2r,4r)-P-menth-8-en-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, (-)-dihydrocarveol is considered to be an isoprenoid lipid molecule (-)-dihydrocarveol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-dihydrocarveol can be found in fats and oils and herbs and spices, which makes (-)-dihydrocarveol a potential biomarker for the consumption of these food products.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(1R,2R,4R)-Dihydrocarveol	ChEBI
(1R,2R,5R)-5-Isopropenyl-2-methylcyclohexanol	ChEBI
(-)-Dihydrocarveol	KEGG

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.2493

Monoisotopic Molecular Weight

154.135765198

IUPAC Name

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

Traditional Name

(-)-dihydrocarveol

CAS Registry Number

20549-47-7

SMILES

C[C@@H]1CC[C@H](C[C@H]1O)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/t8-,9-,10-/m1/s1

InChI Key

KRCZYMFUWVJCLI-OPRDCNLKSA-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

dihydrocarveol (CHEBI:149 )
Menthane monoterpenoids (C11396 )
Cyclic monoterpenes (C11396 )
Menthane monoterpenoids (LMPR0102090031 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0302262)

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 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