| Common Name |
(R)-Piperitone
| Description |
(R)-Piperitone is found in cornmint. (R)-Piperitone is a constituent of Mentha species 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. (Wikipedia).(R)-Piperitone belongs to the family of Monocyclic Monoterpenes. These are monoterpenes containing 1 ring in the isoprene chain.
| Structure |
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Structure for HMDB35737 ((R)-Piperitone)
| Synonyms |
| Value |
Source |
(S)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneChEBI
(S)-PiperitoneChEBI
alpha-PiperitoneChEBI
D-PiperitoneChEBI
a-PiperitoneGenerator
α-piperitoneGenerator
(-)-PiperitoneHMDB
(6R)-3-Methyl-6-(1-methylethyl)-2-cyclohexen-1-oneHMDB
(6R)-3-Methyl-6-(propan-2-yl)cyclohex-2-en-1-oneHMDB
(6R)-6-Isopropyl-3-methylcyclohex-2-en-1-oneHMDB
L-PiperitoneHMDB
| Chemical Formlia |
C10H16O
| Average Molecliar Weight |
152.2334
| Monoisotopic Molecliar Weight |
152.120115134
| IUPAC Name |
(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
| Traditional Name |
α-piperitone
| CAS Registry Number |
4573-50-6
| SMILES |
CC(C)[C@@H]1CCC(C)=CC1=O
| 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
| Chemical Taxonomy |
| Description |
This compound belongs to the class of chemical entities 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 |
Chemical entities
| Super Class |
Organic compounds
| Class |
Lipids and lipid-like moleclies
| Sub Class |
Prenol lipids
| Direct Parent |
Menthane monoterpenoids
| Alternative Parents |
Monocyclic monoterpenoids
Cyclohexenones
Organic oxides
Hydrocarbon derivatives
| Substituents |
P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound
| Molecliar Framework |
Aliphatic homomonocyclic compounds
| External Descriptors |
piperitone (CHEBI:41 )
Menthane monoterpenoids (C09885 )
Cyclic monoterpenes (C09885 )
Menthane monoterpenoids (LMPR0102090024 )
| Ontology |
| Status |
Expected but not Quantified
| Origin |
Endogenous
Food
| Biofunction |
Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability
Nutrient
| Application |
Nutrient
Stabilizers
Surfactants and Emlisifiers
| Cellliar locations |
Cytoplasm
Extracellliar
Membrane
| Physical Properties |
| State |
Not Available
| Experimental Properties |
| Property |
Value |
Reference |
Melting Point-29 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
| Predicted Properties |
| Property |
Value |
Source |
Water Solubility1.36 mg/mLALOGPS
logP2.47ALOGPS
logP3ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.35 m3·mol-1ChemAxon
Polarizability18.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rlie of FiveYesChemAxon
Ghose FilterYesChemAxon
Vebers RlieYesChemAxon
MDDR-like RlieYesChemAxon
| Spectra |
| Spectra |
| Spectrum Type |
Description |
Splash Key |
|
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available
| Predicted LC-MS/MS |
Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available
| Biological Properties |
| Cellliar Locations |
Cytoplasm
Extracellliar
Membrane
| Biofluid Locations |
Not Available
| Tissue Location |
Not Available
| Pathways |
Not Available
| Normal Concentrations |
| Not Available |
| Abnormal Concentrations |
|
Not Available
| Associated Disorders and Diseases |
| Disease References |
None
| Associated OMIM IDs |
None
| External Links |
| DrugBank ID |
Not Available
| DrugBank Metabolite ID |
Not Available
| Phenol Explorer Compound ID |
Not Available
| Phenol Explorer Metabolite ID |
Not Available
| FoodDB ID |
FDB014466
| KNApSAcK ID |
C00010941
| Chemspider ID |
96775
| KEGG Compound ID |
Not Available
| BioCyc ID |
Not Available
| BiGG ID |
Not Available
| Wikipedia Link |
Piperitone
| NuGOwiki Link |
HMDB35737
| Metagene Link |
HMDB35737
| METLIN ID |
Not Available
| PubChem Compound |
107561
| PDB ID |
Not Available
| ChEBI ID |
48934
Product: MKC3947
References |
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| General References |
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
|
PMID: 24027332
