AFCDB: (R)-p-Menth-4(8)-en-3-one (FDB014298)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:11 UTC

Update date

2019-11-26 03:09:48 UTC

Primary ID

FDB014298

Secondary Accession Numbers

FDB014299

Chemical Information

FooDB Name

(R)-p-Menth-4(8)-en-3-one

Description

(R)-p-Menth-4(8)-en-3-one, also known as (+-)-pulegone or isopulegone, 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 (R)-p-Menth-4(8)-en-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

CAS Number

89-82-7

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	2.29 g/L	ALOGPS
logP	2.36	ALOGPS
logP	2.86	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Basic)	-4.4	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	0	ChemAxon
Refractivity	47.13 m³·mol⁻¹	ChemAxon
Polarizability	18.34 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-(propan-2-ylidene)cyclohexan-1-one

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h8H,4-6H2,1-3H3

InChI Key

NZGWDASTMWDZIW-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

enone (CHEBI:26381 )
p-menthane monoterpenoid (CHEBI:26381 )
a monoterpenoid (CPD-4942 )

Ontology

No ontology term

Physico-Chemical Properties

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	< 25 oC
Boiling Point	Bp 224°	DFC
Experimental Water Solubility	Not Available
Experimental logP	3.08	GRIFFIN,S ET AL. (1999)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D +23 (c, 5 in EtOH)	DFC
Spectroscopic UV Data	Not Available
Density	d204 0.94	DFC
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	(R)-p-Menth-4(8)-en-3-one, non-derivatized, GC-MS Spectrum	splash10-0f89-9200000000-103da19d7e73140f53a7	Spectrum
Predicted GC-MS	(R)-p-Menth-4(8)-en-3-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0btm-9600000000-2638fe5c4d411ceee0dc	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-50f4b6a38ec680e83d0c	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-114i-6900000000-7e29b900e574c214c8cb	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldi-9100000000-cb8b1a6e7185079672ba	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-cd90c558f842f253efd3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-011197e33d9b4420c257	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-6900000000-723bf6d0a35d2e10aafd	2015-05-27	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

6722

ChEMBL ID

Not Available

KEGG Compound ID

C09893

Pubchem Compound ID

6988

Pubchem Substance ID

Not Available

ChEBI ID

35596

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35604

CRC / DFC (Dictionary of Food Compounds) ID

JPJ96-T:JPJ72-J

EAFUS ID

3254

Dr. Duke ID

PULEGONE

BIGG ID

Not Available

KNApSAcK ID

C00000827

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1006501

SuperScent ID

442495

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
acetylcholinesterase inhibitor	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE
anti acetylcholinesterase	38462	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.	DUKE
anti Alzheimeran	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cholinesterase	37733	An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8).	DUKE
anti histaminic	37956	Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.	DUKE
anti pyretic	35493	A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.	DUKE
avifuge	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
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
candidicide			DUKE
cerebrotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
encephalopathic			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
glutathionalytic			DUKE
hallucinogenic			DUKE
hepatotoxic	50908	A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.	DUKE
herbicide	24527	A substance used to destroy plant pests.	DUKE
insecticide	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
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
nephrotoxic	50909	A role played by a chemical compound exihibiting itself through the ability to induce damage to the kidney in animals.	DUKE
neurotoxic	50910	A poison that interferes with the functions of the nervous system.	DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	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
pulifuge	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
pulmonotoxic	52209	A role played by the molecular entity or part thereof which causes the development of a pathological process.	DUKE
sedative	35717	A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Flavor	Citations
lime	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
peppermint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
camphor	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.
buchu	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

(R)-p-Menth-4(8)-en-3-one (FDB014298)

Structure for FDB014298 ((R)-p-Menth-4(8)-en-3-one)