Showing Compound Isopulegone (FDB014368)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:14 UTC

Update date

2019-11-26 03:09:55 UTC

Primary ID

FDB014368

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Isopulegone

Description

(-)-trans-isopulegone, also known as isopulegone or 1-methyl-4-isopropenyl-3-cyclohexanone, 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 (-)-trans-isopulegone is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (-)-trans-isopulegone can be found in fats and oils, which makes (-)-trans-isopulegone a potential biomarker for the consumption of this food product.

CAS Number

529-00-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Methyl-4-isopropenyl-3-cyclohexanone	ChEBI
Isopulegone	ChEBI
(+)-Isopulegone	HMDB
(-)-trans-P-Menth-8-en-3-one	HMDB
(2R-trans)-5-Methyl-2-(1-methylethenyl)-cyclohexanone	HMDB
Pulegone, (S)-isomer	MeSH, HMDB
Pulegone, (R)-isomer	MeSH, HMDB
Pulegone	MeSH, HMDB
cis-Isopulegone	MeSH, HMDB
2-Isopropenyl-5-methylcyclohexanone	db_source
5-Methyl-2-(1-methylethenyl)cyclohexanone	db_source
a-Pulegone	db_source
p-Menth-8-en-3-one	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.54 g/L	ALOGPS
logP	2.42	ALOGPS
logP	2.7	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	17.88	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	46.3 m³·mol⁻¹	ChemAxon
Polarizability	18.26 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

Chemical Formula

C10H16O

IUPAC name

5-methyl-2-(prop-1-en-2-yl)cyclohexan-1-one

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8-9H,1,4-6H2,2-3H3

InChI Key

RMIANEGNSBUGDJ-UHFFFAOYSA-N

Isomeric SMILES

CC1CCC(C(C)=C)C(=O)C1

Average Molecular Weight

152.2334

Monoisotopic Molecular Weight

152.120115134

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
Cyclic ketone
Ketone
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:37046 )
a monoterpenoid (CPD-4941 )

Ontology

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 78.90%; H 10.59%; O 10.51%	DFC
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
Predicted GC-MS	(+)-cis-Isopulegone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9200000000-f21ebfb4bb2675e3ee84	Spectrum
Predicted GC-MS	(+)-cis-Isopulegone, 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	splash10-0udi-0900000000-86c22d1bcbce97c1118d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-11or-7900000000-60e1710999312dfb0686	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0pvl-9100000000-eb59a6a329c31dd90fd9	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-a78fe6479a5d6949a074	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-006545b22bbfa3933fdb	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-06rx-9700000000-20b227005a182a539522	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-3900000000-8f6da06f8b0ab70ada65	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-015c-9200000000-d3bd3bc742e7ae79c7e9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-eddd98ab96727b2ed663	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-c373c9eea3cebf186f53	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-7c68a150979e2bd9e798	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-5900000000-6e9f773c05f9e65828bf	2021-09-22	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

JPW05-E:JPW05-E

EAFUS ID

1940

Dr. Duke ID

TRANS-ISOPULEGONE|ISOPULEGONE

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

rw1034221

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
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
pulmonotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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