Showing Compound (-)-Isopulegol acetate (FDB019941)

Record Information

Version

1.0

Creation date

2010-04-08 22:14:41 UTC

Update date

2019-11-26 03:18:08 UTC

Primary ID

FDB019941

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(-)-Isopulegol acetate

Description

Isopulegol acetate 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. Based on a literature review a small amount of articles have been published on Isopulegol acetate.

CAS Number

89-49-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
Isopulegol acetic acid	Generator
1-Methyl-4-isopropenylcyclohexan-3-yl acetate	HMDB
2-Isopropenyl-5-methylcyclohexyl acetate	HMDB
5-Methyl-2-(1-methylethenyl)cyclohexanol acetate	HMDB
Cyclohexanol, 5-methyl-2-(1-methylethenyl), acetate	HMDB
FEMA 2965	HMDB
Isopropenylcyclohexan-3-ol acetate	HMDB
Isopulegolacetate	HMDB
Isopulegyl acetate	HMDB
P-Menth-8-en-3-yl acetate	HMDB
(1R,2S,5R)-5-Methyl-2-(prop-1-en-2-yl)cyclohexyl acetic acid	Generator
(-)-Isopulegol acetic acid	Generator
(-)-Isopulegol acetate	manual
(1R,3R,4S)-(-)-p-Menth-8-en-3-ol acetate	manual
Isopulegol acetate	db_source
p-Menth-8-en-3-yl acetate	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.49	ALOGPS
logP	2.76	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	56.37 m³·mol⁻¹	ChemAxon
Polarizability	22.98 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

(1R,2S,5R)-5-methyl-2-(prop-1-en-2-yl)cyclohexyl acetate

InChI Identifier

InChI=1S/C12H20O2/c1-8(2)11-6-5-9(3)7-12(11)14-10(4)13/h9,11-12H,1,5-7H2,2-4H3/t9-,11+,12-/m1/s1

InChI Key

HLHIVJRLODSUCI-ADEWGFFLSA-N

Isomeric SMILES

C[C@@H]1CC[C@H]([C@@H](C1)OC(C)=O)C(C)=C

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

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Cell and elements:

Extracellular

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 73.43%; H 10.27%; O 16.30%	DFC
Melting Point	Not Available
Boiling Point	Bp8 112-114°	DFC
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	(-)-Isopulegol acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9300000000-cba940c1d1f1aaf19f8e	Spectrum
GC-MS	(-)-Isopulegol acetate, non-derivatized, GC-MS Spectrum	splash10-000f-9700000000-2ac8659513735c5f1608	Spectrum
GC-MS	(-)-Isopulegol acetate, non-derivatized, GC-MS Spectrum	splash10-0006-9300000000-cba940c1d1f1aaf19f8e	Spectrum
GC-MS	(-)-Isopulegol acetate, non-derivatized, GC-MS Spectrum	splash10-000f-9700000000-2ac8659513735c5f1608	Spectrum
Predicted GC-MS	(-)-Isopulegol acetate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4l-9400000000-782001fc756db8f2ed3e	Spectrum
Predicted GC-MS	(-)-Isopulegol 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	splash10-0002-0900000000-c310b45afbf8bebec140	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-5900000000-74e3c99e5e97bce0a7aa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aor-9100000000-7b358df4198c2d161d6c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f6t-0900000000-a51ca72efa8995b84a7d	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-2900000000-5a26b25a09d1449267f5	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0m53-5900000000-6e0fbbcee54aa6be4254	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-9500000000-93096a7d46cef7b4b612	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001m-9400000000-3834eca8ad8d46f748bc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-16c4be2637c6fc12fd2c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-9500000000-01f5d7361d665b4a2f29	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-9200000000-c7e76a2ea7308d0c72da	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-4be60751d3ccfe7fd79a	2021-09-24	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

85346

ChEMBL ID

CHEMBL3120645

KEGG Compound ID

Not Available

Pubchem Compound ID

94579

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB40227

CRC / DFC (Dictionary of Food Compounds) ID

JXJ74-P:MGX91-C

EAFUS ID

1941

Dr. Duke ID

ISOPULEGOL-ACETATE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

89-49-6

GoodScent ID

rw1014371

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

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
mint	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
leaf	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
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
peppermint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
tropical	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.