ChemFOnt: Showing chemical card for (S)-alpha-Terpinyl acetate (CFc000336884)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:30:17 UTC

Chemfont ID

CFc000336884

Molecule Identification

Common Name

(S)-alpha-Terpinyl acetate

Definition

(±)-alpha-terpinyl acetate, also known as P-menth-1-en-8-yl acetate or (±)-α-terpinyl acetic acid, 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, (±)-alpha-terpinyl acetate is considered to be an isoprenoid lipid molecule (±)-alpha-terpinyl acetate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). (±)-alpha-terpinyl acetate is a bergamot, citrus, and herbal tasting compound and can be found in a number of food items such as sweet basil, roselle, cardamom, and mandarin orange (clementine, tangerine), which makes (±)-alpha-terpinyl acetate a potential biomarker for the consumption of these food products (±)-alpha-terpinyl acetate can be found primarily in saliva (±)-alpha-terpinyl acetate exists in all eukaryotes, ranging from yeast to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
p-Menth-1-en-8-yl acetate	Kegg
p-Menth-1-en-8-yl acetic acid	Generator
a-Terpineol acetate	Generator
a-Terpineol acetic acid	Generator
alpha-Terpineol acetic acid	Generator
Α-terpineol acetate	Generator
Α-terpineol acetic acid	Generator
FEMA 3047	HMDB
a-Terpinyl acetate	Generator
a-Terpinyl acetic acid	Generator
alpha-Terpinyl acetic acid	Generator
Α-terpinyl acetate	Generator
Α-terpinyl acetic acid	Generator

Chemical Formula

C₁₂H₂₀O₂

Average Molecular Weight

196.286

Monoisotopic Molecular Weight

196.146329884

IUPAC Name

2-(4-methylcyclohex-3-en-1-yl)propan-2-yl acetate

Traditional Name

α-terpinyl acetate

CAS Registry Number

58206-95-4

SMILES

CC(=O)OC(C)(C)C1CCC(C)=CC1

InChI Identifier

InChI=1S/C12H20O2/c1-9-5-7-11(8-6-9)12(3,4)14-10(2)13/h5,11H,6-8H2,1-4H3

InChI Key

IGODOXYLBBXFDW-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
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

p-menthane monoterpenoid (CHEBI:32320 )
Menthane monoterpenoids (C12300 )
Cyclic monoterpenes (C12300 )
Menthane monoterpenoids (LMPR0102090045 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0032051)

Food

Herb and spice

Spice

Cardamom (FooDB: FOOD00074)

Vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	4.32	ALOGPS
logP	2.62	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.61 m³·mol⁻¹	ChemAxon
Polarizability	23.05 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0032051

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

111037

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for (S)-alpha-Terpinyl acetate (CFc000336884)

MOL for CFc000336884 ((S)-alpha-Terpinyl acetate)

3D MOL for CFc000336884 ((S)-alpha-Terpinyl acetate)

3D SDF for CFc000336884 ((S)-alpha-Terpinyl acetate)

3D-SDF for CFc000336884 ((S)-alpha-Terpinyl acetate)

PDB for CFc000336884 ((S)-alpha-Terpinyl acetate)

3D PDB for CFc000336884 ((S)-alpha-Terpinyl acetate)

SMILES for CFc000336884 ((S)-alpha-Terpinyl acetate)

INCHI for CFc000336884 ((S)-alpha-Terpinyl acetate)

Structure for CFc000336884 ((S)-alpha-Terpinyl acetate)

3D Structure for CFc000336884 ((S)-alpha-Terpinyl acetate)