Showing Compound (R)-Piperitone (FDB014466)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:17 UTC

Update date

2019-11-26 03:10:06 UTC

Primary ID

FDB014466

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-Piperitone

Description

Constituent of Mentha subspecies and Zanthoxylum piperitum (Japanese pepper tree) oil Piperitone is a natural monoterpene ketone which is a component of some essential oils. Both stereoisomers, the D-form and the L-form, are known. The D-form has a peppermint-like aroma and has been isolated from the oils of plants from the genera Cymbopogon, Andropogon, and Mentha. The L-form has been isolated from Sitka spruce. (R)-Piperitone is found in cornmint, spearmint, and herbs and spices.

CAS Number

4573-50-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one	ChEBI
(S)-Piperitone	ChEBI
alpha-Piperitone	ChEBI
D-Piperitone	ChEBI
a-Piperitone	Generator
Α-piperitone	Generator
(-)-Piperitone	HMDB
(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-one	HMDB
(6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-one	HMDB
(6R)-6-Isopropyl-3-methylcyclohex-2-en-1-one	HMDB
L-Piperitone	HMDB
(R)-6-(Isopropyl)-3-methylcyclohex-2-en-1-one	ChEBI

Predicted Properties

Property	Value	Source
Water Solubility	1.36 g/L	ALOGPS
logP	2.47	ALOGPS
logP	3	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	18.87	ChemAxon
pKa (Strongest Basic)	-4.6	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	47.35 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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

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

InChI Identifier

InChI=1S/C10H16O/c1-7(2)9-5-4-8(3)6-10(9)11/h6-7,9H,4-5H2,1-3H3/t9-/m0/s1

InChI Key

YSTPAHQEHQSRJD-VIFPVBQESA-N

Isomeric SMILES

CC(C)[C@@H]1CCC(C)=CC1=O

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
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

piperitone (CHEBI:41 )
Menthane monoterpenoids (C09885 )
Cyclic monoterpenes (C09885 )
Menthane monoterpenoids (LMPR0102090024 )

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:

Biological role:

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	Mp -29°	DFC
Boiling Point	Bp15 110.5°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]20D -51.53	DFC
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	(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00kf-9300000000-e3bec6231e4993e3d578	Spectrum
Predicted GC-MS	(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-Piperitone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	(R)-Piperitone, 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-0900000000-0f2176d975b2f9bfe7fd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-7900000000-bc07a247759df113c943	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-6e8d2587c3fab7a87b03	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-83fb585962f6ed48b378	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0900000000-a2b215f78ea2edceb56c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4u-8900000000-058070ac2054c97f9a30	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0w29-1900000000-cf5ff8ec6a34a5b6435b	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0gb9-9200000000-ddaec970d54edc7cbf79	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-4c75828fad35f0eec374	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-0900000000-3f9a24ef7ca3da32a522	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9400000000-172af5b361384699caf7	2021-09-22	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

96775

ChEMBL ID

CHEMBL2229207

KEGG Compound ID

Not Available

Pubchem Compound ID

107561

Pubchem Substance ID

Not Available

ChEBI ID

48934

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB35737

CRC / DFC (Dictionary of Food Compounds) ID

JFJ29-J:JQZ89-C

EAFUS ID

3058

Dr. Duke ID

(-)-PIPERITONE

BIGG ID

Not Available

KNApSAcK ID

C00010941

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1389401

SuperScent ID

Not Available

Wikipedia ID

Piperitone

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 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

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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