ChemFOnt: Showing chemical card for 1,4-Terpinenol (CFc000333289)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:14 UTC

Chemfont ID

CFc000333289

Molecule Identification

Common Name

1,4-Terpinenol

Definition

Terpinen-4-ol, also known as (+-)-P-menth-1-en-4-ol or terpinenol-4, 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. Terpinen-4-ol is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Terpinen-4-ol is a sweet, earth, and musty tasting compound and can be found in a number of food items such as rosemary, saffron, sweet basil, and chinese cinnamon, which makes terpinen-4-ol a potential biomarker for the consumption of these food products. Terpinen-4-ol can be found primarily in feces. Terpinen-4-ol exists in all eukaryotes, ranging from yeast to humans. Terpinen-4-ol occurs in Juniperus communis and is thought to be the reason this wood is highly resistant to rot. Norwegian farmers used to exploit this by making fence poles out of juniper. The concentration is higher in the alpine subspecies of juniper, but occurs in both subspecies .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-p-Menth-1-en-4-ol	ChEBI
1-Isopropyl-4-methylcyclohex-3-en-1-ol	ChEBI
1-Menthene-4-ol	ChEBI
1-Methyl-4-isopropyl-1-cyclohexen-4-ol	ChEBI
1-p-Menthen-4-ol	ChEBI
1-Para-menthen-4-ol	ChEBI
1-Terpinen-4-ol	ChEBI
4-Carvomenthenol	ChEBI
4-Methyl-1-(1-methylethyl)-3-cyclohexen-1-ol	ChEBI
4-Methyl-1-isopropyl-3-cyclohexen-1-ol	ChEBI
alpha-Terpinen-4-ol	ChEBI
Terpene-4-ol	ChEBI
Terpin-4-en-1-ol	ChEBI
Terpinen-4-ol	ChEBI
Terpinene-4-ol	ChEBI
Terpinenol-4	ChEBI
Terpineol-4	ChEBI
a-Terpinen-4-ol	Generator
Α-terpinen-4-ol	Generator
1-Isopropyl-4-methyl-3-cyclohexen-1-ol	HMDB
4-Terpineol	HMDB
alpha -Terpinen-4-ol	HMDB
FEMA 2248	HMDB
Origanol	HMDB
p-Menth-1-en-4-ol	ChEBI
(R)-1-Isopropyl-4-methyl-3-cyclohexen-1-ol	MeSH

Chemical Formula

C₁₀H₁₈O

Average Molecular Weight

154.253

Monoisotopic Molecular Weight

154.1357652

IUPAC Name

4-methyl-1-(propan-2-yl)cyclohex-3-en-1-ol

Traditional Name

terpinen-4-ol

CAS Registry Number

562-74-3

SMILES

CC(C)C1(O)CCC(C)=CC1

InChI Identifier

InChI=1S/C10H18O/c1-8(2)10(11)6-4-9(3)5-7-10/h4,8,11H,5-7H2,1-3H3

InChI Key

WRYLYDPHFGVWKC-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
Tertiary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

tertiary alcohol (CHEBI:78884 )
terpineol (CHEBI:78884 )
Menthane monoterpenoids (C17073 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0035833)

Food

Herb and spice

Herb

Dill (FooDB: FOOD00013)
Sweet marjoram (FooDB: FOOD00122)

Fruit

Berry

Grape (FooDB: FOOD00369)

Citrus

Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Beverage

Fermented beverage

Grape wine (FooDB: FOOD00612)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	2.5 g/L	ALOGPS
logP	2.81	ALOGPS
logP	2.33	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	20	ChemAxon
pKa (Strongest Basic)	-0.61	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	48.31 m³·mol⁻¹	ChemAxon
Polarizability	18.7 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