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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:36:37 UTC
Update Date2022-03-07 02:54:34 UTC
HMDB IDHMDB0035601
Secondary Accession Numbers
  • HMDB35601
Metabolite Identification
Common Name(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one
Description(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one is found in citrus. (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one occurs in peppermint oil, green tea and bergamot oranges (Citrus bergamia).Jasmone is a natural organic compound extracted from the volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid that has the odor of jasmine. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture containing both forms, with the cis form predominating. Both forms have similar odors and chemical properties. (Wikipedia
Structure
Data?1563862743
Synonyms
ValueSource
cis-JasmoneKegg
(Z)-JasmoneHMDB, MeSH
2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)- (8ci)HMDB
2-Cyclopenten-1-one, 3-methyl-2-(2Z)-2-pentenyl- (9ci)HMDB
3-Methyl-2-[(2Z)-2-pentenyl]-2-cyclopenten-1-oneHMDB
cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneHMDB
JasmoneMeSH, HMDB
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneMeSH
Chemical FormulaC11H16O
Average Molecular Weight164.2441
Monoisotopic Molecular Weight164.120115134
IUPAC Name3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Traditional Namejasmone
CAS Registry Number488-10-8
SMILES
CC\C=C/CC1=C(C)CCC1=O
InChI Identifier
InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4-
InChI KeyXMLSXPIVAXONDL-PLNGDYQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclic ketones
Alternative Parents
Substituents
  • Cyclic ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point134.00 to 135.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility1514 mg/L @ 20 °C (exp)The Good Scents Company Information System
LogP2.905 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.7 g/LALOGPS
logP3.32ALOGPS
logP3.1ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity52.9 m³·mol⁻¹ChemAxon
Polarizability19.79 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.18531661259
DarkChem[M-H]-135.1831661259
DeepCCS[M+H]+143.77430932474
DeepCCS[M-H]-139.94630932474
DeepCCS[M-2H]-177.05130932474
DeepCCS[M+Na]+152.62730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneCC\C=C/CC1=C(C)CCC1=O1952.4Standard polar33892256
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneCC\C=C/CC1=C(C)CCC1=O1366.8Standard non polar33892256
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-oneCC\C=C/CC1=C(C)CCC1=O1372.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one,1TMS,isomer #1CC/C=C\CC1=C(C)CC=C1O[Si](C)(C)C1520.0Semi standard non polar33892256
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one,1TMS,isomer #1CC/C=C\CC1=C(C)CC=C1O[Si](C)(C)C1519.6Standard non polar33892256
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one,1TBDMS,isomer #1CC/C=C\CC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C1748.1Semi standard non polar33892256
(Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one,1TBDMS,isomer #1CC/C=C\CC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C1685.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one EI-B (Non-derivatized)splash10-03dl-9700000000-626f6beb94dae241c8a72018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one EI-B (Non-derivatized)splash10-01r6-9600000000-b7842817d55e1ef34cd52018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4u-6900000000-4ec9a03205a62c5db5712017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 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 - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-014i-1900000000-b3455ba1815cd60172a32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-066r-7900000000-df4da4ed2a42175313612016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-0uxu-9100000000-1ad974119b61c19d8fcb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-03di-0900000000-54214296816474e678192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-03di-0900000000-9e2bcdc11fb8c55163ab2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-0006-9800000000-3aa25aca2cc0986b4e112016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 10V, Positive-QTOFsplash10-0900-5900000000-150eb84c8131eaddd8062021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 20V, Positive-QTOFsplash10-052f-9300000000-4c74719ab790c3d97cb72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 40V, Positive-QTOFsplash10-0536-9000000000-eac87e59851b2c86a2102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 10V, Negative-QTOFsplash10-03di-0900000000-defd12a7f890bc9459182021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 20V, Negative-QTOFsplash10-03di-0900000000-7005ce6951d5a76167cd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (Z)-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one 40V, Negative-QTOFsplash10-066r-4900000000-524d8ff912c0d662ad372021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB014294
KNApSAcK IDC00001313
Chemspider ID1266012
KEGG Compound IDC08490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1549018
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016891
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .