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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:14:31 UTC
Update Date2023-02-21 17:25:32 UTC
HMDB IDHMDB0036999
Secondary Accession Numbers
  • HMDB36999
Metabolite Identification
Common NamePiperitenone
DescriptionPiperitenone 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. Thus, piperitenone is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Piperitenone.
Structure
Data?1677000332
Synonyms
ValueSource
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-oneHMDB
3-Methyl-6-(1-methylethylidene)-2-cyclohexen-1-one, 9ciHMDB
3-Methyl-6-propan-2-ylidenecyclohex-2-en-1-oneHMDB
3-TerpinolenoneHMDB
6-Isopropylidene-3-methyl-2-cyclohexenoneHMDB
FEMA 3560HMDB
PulespenoneHMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name3-methyl-6-(propan-2-ylidene)cyclohex-2-en-1-one
Traditional Namepiperitenone
CAS Registry Number491-09-8
SMILES
CC(C)=C1CCC(C)=CC1=O
InChI Identifier
InChI=1S/C10H14O/c1-7(2)9-5-4-8(3)6-10(9)11/h6H,4-5H2,1-3H3
InChI KeyHKZQJZIFODOLFR-UHFFFAOYSA-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
  • Quinomethane
  • O-quinomethane
  • 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
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point106.00 to 107.00 °C. @ 10.00 mm HgThe Good Scents Company Information System
Water Solubility164.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.766 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility2.05 g/LALOGPS
logP2.39ALOGPS
logP2.81ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)18.6ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.96 m³·mol⁻¹ChemAxon
Polarizability17.77 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]+136.01331661259
DarkChem[M-H]-132.76431661259
DeepCCS[M+H]+134.38430932474
DeepCCS[M-H]-130.62630932474
DeepCCS[M-2H]-168.03430932474
DeepCCS[M+Na]+143.3730932474
AllCCS[M+H]+130.632859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+134.932859911
AllCCS[M+Na]+136.132859911
AllCCS[M-H]-134.432859911
AllCCS[M+Na-2H]-135.932859911
AllCCS[M+HCOO]-137.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PiperitenoneCC(C)=C1CCC(C)=CC1=O1843.2Standard polar33892256
PiperitenoneCC(C)=C1CCC(C)=CC1=O1290.2Standard non polar33892256
PiperitenoneCC(C)=C1CCC(C)=CC1=O1314.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Piperitenone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f7c-8900000000-f5b1034f0ad5612f0f1e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Piperitenone 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 - Piperitenone 10V, Positive-QTOFsplash10-0udi-0900000000-c4031753132982c55fab2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 20V, Positive-QTOFsplash10-0pb9-7900000000-9a0d9372d2684846d39b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 40V, Positive-QTOFsplash10-0gb9-9100000000-82fba962be7e9686c5172017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 10V, Negative-QTOFsplash10-0002-0900000000-b7c0004066c195aa40892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 20V, Negative-QTOFsplash10-0002-0900000000-49abeb92134d82dda90e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 40V, Negative-QTOFsplash10-053s-2900000000-fba0f16e8603dd89ee042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 10V, Positive-QTOFsplash10-0udi-1900000000-7be39bdd81d4a83f56ee2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 20V, Positive-QTOFsplash10-00kf-9300000000-b6529814b27363caeb9a2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 40V, Positive-QTOFsplash10-0006-9000000000-51ccd861c84166dd6b2c2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 10V, Negative-QTOFsplash10-0002-0900000000-22917433edc8ad9dbc2e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 20V, Negative-QTOFsplash10-0002-0900000000-cfb5c45cee930f53ee1b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Piperitenone 40V, Negative-QTOFsplash10-0159-9100000000-afc2d70a9cbeb08c12302021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB015974
KNApSAcK IDC00010889
Chemspider ID337757
KEGG Compound IDC01951
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound381152
PDB IDNot Available
ChEBI ID17304
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1031141
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Romagnoli C, Bruni R, Andreotti E, Rai MK, Vicentini CB, Mares D: Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L. Protoplasma. 2005 Apr;225(1-2):57-65. Epub 2005 May 4. [PubMed:15868213 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.