Showing Compound Piperitenone (FDB015974)

Record Information

Version

1.0

Creation date

2010-04-08 22:12:10 UTC

Update date

2020-09-17 15:30:28 UTC

Primary ID

FDB015974

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Piperitenone

Description

Piperitenone belongs to the class of organic compounds known as menthane 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, piperitenone is an isoprenoid lipid molecule. It is very hydrophobic, almost insoluble in water, and relatively neutral. Piperitenone is a minty, phenolic, and sharp-taste ( http://www.thegoodscentscompany.com/data/rw1031141.html). Piperitenone is found in highest concentrations in spearmints and rosemaries. It was detected in peppermints, herbs and spices, orange mints, citrus, and mentha (mint). This could make piperitenone a potential biomarker for the consumption of these foods.

CAS Number

491-09-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one	HMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ci	HMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-one	HMDB
3-Terpinolenone	HMDB
6-Isopropylidene-3-methyl-2-cyclohexenone	HMDB
FEMA 3560	HMDB
Pulespenone	HMDB
2-Cyclohexen-1-one, 3-methyl-6-(1-methylethylidene)-	biospider
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9CI	db_source
3-methyl-6-propan-2-ylidenecyclohex-2-en-1-one	biospider
Piperitenone	db_source

Predicted Properties

Property	Value	Source
Water Solubility	2.05 g/L	ALOGPS
logP	2.39	ALOGPS
logP	2.81	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	18.6	ChemAxon
pKa (Strongest Basic)	-3.9	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	47.96 m³·mol⁻¹	ChemAxon
Polarizability	17.77 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

C10H14O

IUPAC name

3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one

InChI Identifier

InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3

InChI Key

HKZQJZIFODOLFR-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

150.2176

Monoisotopic Molecular Weight

150.10446507

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
Quinomethane
O-quinomethane
Cyclohexenone
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-menthadien-3-one (CHEBI:17304 )
Menthane monoterpenoids (C01951 )
Cyclic monoterpenes (C01951 )
Menthane monoterpenoids (LMPR0102090056 )
a small molecule (CPD-278 )

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 79.96%; H 9.39%; O 10.65%	DFC
Melting Point	Not Available
Boiling Point	Bp14 120-122°	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
Predicted GC-MS	Piperitenone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f7c-8900000000-f5b1034f0ad5612f0f1e	Spectrum
Predicted GC-MS	Piperitenone, 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-c4031753132982c55fab	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-7900000000-9a0d9372d2684846d39b	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9100000000-82fba962be7e9686c517	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-b7c0004066c195aa4089	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-49abeb92134d82dda90e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053s-2900000000-fba0f16e8603dd89ee04	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-7be39bdd81d4a83f56ee	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-b6529814b27363caeb9a	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-51ccd861c84166dd6b2c	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-22917433edc8ad9dbc2e	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-0900000000-cfb5c45cee930f53ee1b	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0159-9100000000-afc2d70a9cbeb08c1230	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17304

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36999

CRC / DFC (Dictionary of Food Compounds) ID

KLQ60-W:KLQ60-W

EAFUS ID

3055

Dr. Duke ID

(+)-PIPERITENONE|PIPERITENONE

BIGG ID

Not Available

KNApSAcK ID

C00010889

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1031141

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
Anti acetylcholinesterase	38462	An agent that inhibits acetylcholinesterase, increasing acetylcholine levels. It enhances cholinergic transmission, used therapeutically to treat Alzheimer's disease, myasthenia gravis, and glaucoma, improving cognitive function, muscle strength, and reducing intraocular pressure.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Toxic	52209	A substance that can harm or poison living organisms. Biologically, it can disrupt cellular functions and cause damage. Therapeutically, toxins are used in small, controlled doses for applications such as cancer treatment and immunosuppression. Key medical uses include chemotherapy and immunotherapy, where toxins are used to target and destroy diseased cells.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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