ChemFOnt: Showing chemical card for alpha-Terpinene (CFc000017931)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:08:09 UTC

Chemfont ID

CFc000017931

Molecule Identification

Common Name

alpha-Terpinene

Definition

Alpha-Terpinene is one of four isomers of terpinene (the other three being beta terpinene, gamma terpenine, and delta terpinine or terpimolene) that differ in the position of carbon-carbon double bonds. Alpha-Terpinene belongs to the class of organic compounds known as menthane monoterpenes. These are monoterpenes 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. alpha-Terpinene is a naturally occurring monoterpene found in allspice, cardamom, and marjoram. alpha-Terpinene is a constituent of many essential oils with oil from Litsea ceylanica being is a major source (20%) of it. alpha-Terpinene has been found in Citrus, Eucalyptus and Juniperus species, and cannabis plants (PMID:6991645 ). ±-Terpinene is a flavouring agent and is produced industrially by acid-catalyzed rearrangement of ±-pinene. It has perfume and flavoring properties but is mainly used to confer a pleasant odor to industrial fluids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Isopropyl-4-methyl-1,3-cyclohexadiene	ChEBI
1-Methyl-4-(1-methylethyl)-1,3-cyclohexadiene	ChEBI
p-Mentha-1,3-diene	ChEBI
Terpilene	ChEBI
a-Terpinene	Generator
Α-terpinene	Generator
1-Isopropyl-4-methyl-cyclohexa-1,3-diene	HMDB
1-Isopropyl-4-methylcyclohexa-1,3-diene	HMDB
1-Methyl-4-(propan-2-yl)cyclohexa-1,3-diene	HMDB
1-Methyl-4-isopropyl-1,3-cyclohexadiene	HMDB
1-Methyl-4-isopropylcyclohexadiene-1,3	HMDB
alpha -Terpinene	HMDB
FEMA 3558	HMDB
1,4-p-Menthadiene	HMDB
beta-Terpinene	HMDB
gamma-Terpinene	HMDB
4-Isopropyl-1-methyl-1,3-cyclohexadiene	PhytoBank
alpha-Terpinen	PhytoBank
α-Terpinen	PhytoBank
alpha-Terpinene	PhytoBank

Chemical Formula

C₁₀H₁₆

Average Molecular Weight

136.238

Monoisotopic Molecular Weight

136.125200515

IUPAC Name

1-methyl-4-(propan-2-yl)cyclohexa-1,3-diene

Traditional Name

terpinene

CAS Registry Number

99-86-5

SMILES

CC(C)C1=CC=C(C)CC1

InChI Identifier

InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8H,5,7H2,1-3H3

InChI Key

YHQGMYUVUMAZJR-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
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

monoterpene (CHEBI:10334 )
Menthane monoterpenoids (C09898 )
Cyclic monoterpenes (C09898 )
Menthane monoterpenoids (LMPR0102090026 )
a monoterpenoid (CPD-8735 )

Functional Ontology

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 24421258)

Cellular substructure

Extracellular (HMDB: HMDB0036995)
Membrane (HMDB: HMDB0036995)

Source

Exogenous

Exogenous (HMDB: HMDB0036995)

White cabbage (FooDB: FOOD00887)
Cabbage (FooDB: FOOD00851)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Sunflower (FooDB: FOOD00086)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)
Citrus (FooDB: FOOD00859)

Tropical fruit

Papaya (FooDB: FOOD00041)

Endogenous

Endogenous (HMDB: HMDB0036995)

Not Available

EC 3.4.15.1 (peptidyl-dipeptidase A) inhibitor (HMDB: HMDB0036995)
EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0036995)
EC 3.1.1.7 (acetylcholinesterase) inhibitor (HMDB: HMDB0036995)
P450 inhibitor (HMDB: HMDB0036995)

Enzyme inhibitor

Angiotensin converting enzyme inhibitor (HMDB: HMDB0036995)

Industrial application

Agriculture

Pesticide

Acaricide (HMDB: HMDB0036995)
Insecticide (HMDB: HMDB0036995)

Pesticide (HMDB: HMDB0036995)

Food and nutrition

Food additive

Flavoring agent

Flavor (HMDB: HMDB0036995)

Fragrance (HMDB: HMDB0036995)

Pharmaceutical industry

Spasmogenic (HMDB: HMDB0036995)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.5 g/L	ALOGPS
logP	4.51	ALOGPS
logP	3.16	ChemAxon
logS	-2.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	47.55 m³·mol⁻¹	ChemAxon
Polarizability	17.59 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