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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:45:13 UTC
Update Date2021-10-13 06:51:04 UTC
HMDB IDHMDB0035737
Secondary Accession Numbers
  • HMDB35737
Metabolite Identification
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)
Structure
Data?1563862764
Synonyms
ValueSource
(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 FormulaC10H16O
Average Molecular Weight152.2334
Monoisotopic Molecular Weight152.120115134
IUPAC Name(6S)-3-methyl-6-(propan-2-yl)cyclohex-2-en-1-one
Traditional Nameα-piperitone
CAS Registry Number4573-50-6
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 KeyYSTPAHQEHQSRJD-VIFPVBQESA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane 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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-29 °CNot Available
Boiling Point233.00 to 235.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility273.1 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.004 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP10(2.47) g/LALOGPS
logP10(3) g/LChemAxon
logS10(-2) g/LALOGPS
pKa (Strongest Acidic)18.87ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.35 m³·mol⁻¹ChemAxon
Polarizability18.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.30931661259
DarkChem[M-H]-135.36931661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-PiperitoneCC(C)[C@@H]1CCC(C)=CC1=O1690.2Standard polar33892256
(R)-PiperitoneCC(C)[C@@H]1CCC(C)=CC1=O1195.7Standard non polar33892256
(R)-PiperitoneCC(C)[C@@H]1CCC(C)=CC1=O1230.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Piperitone,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC11391.6Semi standard non polar33892256
(R)-Piperitone,1TMS,isomer #1CC1=CC(O[Si](C)(C)C)=C(C(C)C)CC11333.6Standard non polar33892256
(R)-Piperitone,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC11626.1Semi standard non polar33892256
(R)-Piperitone,1TBDMS,isomer #1CC1=CC(O[Si](C)(C)C(C)(C)C)=C(C(C)C)CC11540.8Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Piperitone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-9300000000-e3bec6231e4993e3d5782017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Piperitone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Piperitone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Piperitone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 10V, Positive-QTOFsplash10-0udi-0900000000-0f2176d975b2f9bfe7fd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 20V, Positive-QTOFsplash10-0w29-7900000000-bc07a247759df113c9432016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 40V, Positive-QTOFsplash10-0a4l-9000000000-6e8d2587c3fab7a87b032016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 10V, Negative-QTOFsplash10-0udi-0900000000-83fb585962f6ed48b3782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 20V, Negative-QTOFsplash10-0udi-0900000000-a2b215f78ea2edceb56c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 40V, Negative-QTOFsplash10-0a4u-8900000000-058070ac2054c97f9a302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 10V, Positive-QTOFsplash10-0w29-1900000000-cf5ff8ec6a34a5b6435b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 20V, Positive-QTOFsplash10-0gb9-9200000000-ddaec970d54edc7cbf792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 40V, Positive-QTOFsplash10-00kf-9000000000-4c75828fad35f0eec3742021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 10V, Negative-QTOFsplash10-0udi-0900000000-c373c9eea3cebf186f532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 20V, Negative-QTOFsplash10-0udi-0900000000-3f9a24ef7ca3da32a5222021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Piperitone 40V, Negative-QTOFsplash10-014i-9400000000-172af5b361384699caf72021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014467
KNApSAcK IDC00003054
Chemspider ID55294
KEGG Compound IDC09885
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107561
PDB IDNot Available
ChEBI ID41
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1002881
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.