AFCDB: alpha-Terpinyl acetate (FDB003994)

Record Information

Version

1.0

Creation date

2010-04-08 22:06:02 UTC

Update date

2019-11-26 02:59:43 UTC

Primary ID

FDB003994

Secondary Accession Numbers

FDB008756

Chemical Information

FooDB Name

alpha-Terpinyl acetate

Description

(±)-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 hyssop, rosemary, sweet bay, and roselle, which makes (±)-alpha-terpinyl acetate a potential biomarker for the consumption of these food products (±)-alpha-terpinyl acetate can be found primarily in saliva.

CAS Number

8007-35-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Not Available	Not Available

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

Chemical Formula

C12H20O2

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

196.286

Monoisotopic Molecular Weight

196.146329884

Classification

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Biological role:

Industrial application:

Food and nutrition:

Flavoring agent

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	alpha-Terpinyl acetate, non-derivatized, GC-MS Spectrum	splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8	Spectrum
GC-MS	alpha-Terpinyl acetate, non-derivatized, GC-MS Spectrum	splash10-006x-9500000000-ffe7aaa2d3a38a8ed5b8	Spectrum
Predicted GC-MS	alpha-Terpinyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9200000000-b8293aa3446037e3fc50	Spectrum
Predicted GC-MS	alpha-Terpinyl acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-1900000000-3882c1dcf928825bf3ba	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052k-6900000000-b4a6d18cb758c8c91aa1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-1010-9300000000-257ef5e703a03c85b0b1	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1900000000-5359896272e433550068	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-3900000000-5a9af9efd8065cc02e7a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-7900000000-143c587d14b196b024ab	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-6900000000-6c4255f51fb20737cf52	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001u-9300000000-406d5fb45faab3d92142	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9100000000-04361680a71103d6a965	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-1900000000-94fa9d6a65fb7d565891	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052r-3900000000-37fb80ce31389d8421e1	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9500000000-5a05b8a2e1912b54660b	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

TERPINEOL-ACETATE|TERPENYL-ACETATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1375491

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
pesticide	25944	Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
herbal	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bergamot	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
pine	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
wax	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

alpha-Terpinyl acetate (FDB003994)

Structure for FDB003994 (alpha-Terpinyl acetate)