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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:44:05 UTC
Update Date2019-07-23 06:09:01 UTC
HMDB IDHMDB0031565
Secondary Accession Numbers
  • HMDB31565
Metabolite Identification
Common NameDihydrojasmone
DescriptionDihydrojasmone 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. Dihydrojasmone is a fresh, herbal, and jasmin tasting compound. Dihydrojasmone has been detected, but not quantified in, citrus. This could make dihydrojasmone a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on Dihydrojasmone.
Structure
Data?1563862141
Synonyms
ValueSource
2-Amyl-3-methyl-2-cyclopenten-1-oneHMDB
2-N-Pentyl-3-methyl-2-cyclopenten-1-oneHMDB
2-Pentyl-3-methyl-2-cyclopenten-1-oneHMDB
3-Methyl-2-(N-pentanyl)-2-cyclopenten-1-oneHMDB, MeSH
3-Methyl-2-pentyl-2-cyclopenten-1-oneHMDB
3-Methyl-2-pentyl-cyclopent-2-enoneHMDB
3-Methyl-2-pentylcyclopent-2-en-1-oneHMDB
3-Methyl-2-pentylcyclopent-2-enoneHMDB
dihydro-JasmoneHMDB
FEMA 3763HMDB
Jasmone,dihydroHMDB
TetrahydropyrethroneHMDB
Chemical FormulaC11H18O
Average Molecular Weight166.26
Monoisotopic Molecular Weight166.135765198
IUPAC Name3-methyl-2-pentylcyclopent-2-en-1-one
Traditional Name3-methyl-2-pentylcyclopent-2-en-1-one
CAS Registry Number1128-08-1
SMILES
CCCCCC1=C(C)CCC1=O
InChI Identifier
InChI=1S/C11H18O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h3-8H2,1-2H3
InChI KeyYCIXWYOBMVNGTB-UHFFFAOYSA-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 DescriptorsNot Available
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP10(3.55) g/LALOGPS
logP10(3.46) g/LChemAxon
logS10(-2.3) g/LALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity51.78 m³·mol⁻¹ChemAxon
Polarizability20.66 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]+141.75131661259
DarkChem[M-H]-136.70631661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DihydrojasmoneCCCCCC1=C(C)CCC1=O1894.2Standard polar33892256
DihydrojasmoneCCCCCC1=C(C)CCC1=O1370.8Standard non polar33892256
DihydrojasmoneCCCCCC1=C(C)CCC1=O1356.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Dihydrojasmone,1TMS,isomer #1CCCCCC1=C(C)CC=C1O[Si](C)(C)C1508.4Semi standard non polar33892256
Dihydrojasmone,1TMS,isomer #1CCCCCC1=C(C)CC=C1O[Si](C)(C)C1529.7Standard non polar33892256
Dihydrojasmone,1TBDMS,isomer #1CCCCCC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C1724.6Semi standard non polar33892256
Dihydrojasmone,1TBDMS,isomer #1CCCCCC1=C(C)CC=C1O[Si](C)(C)C(C)(C)C1678.0Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0iml-9400000000-a9ad6584e7f14ccde4f32017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-02hj-9700000000-fbe45b6deff4c436a7882017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0ik9-7900000000-79a7d490f28c7bc92c642017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0ikc-7900000000-c07ace9e4f88c96f29cf2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0iml-9400000000-a9ad6584e7f14ccde4f32018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-02hj-9700000000-fbe45b6deff4c436a7882018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0ik9-7900000000-79a7d490f28c7bc92c642018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Dihydrojasmone EI-B (Non-derivatized)splash10-0ikc-7900000000-c07ace9e4f88c96f29cf2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrojasmone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9700000000-6b8a4052589c5f46caee2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Dihydrojasmone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-7b2779bb29dca9d02c672017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone LC-ESI-QTOF , positive-QTOFsplash10-014i-0900000000-05d13aeec0ec1585b4fa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone LC-ESI-QTOF , positive-QTOFsplash10-092a-4900000000-9ecbc817bebd6b19e66d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone LC-ESI-QTOF , positive-QTOFsplash10-0btd-7900000000-7209912290de3f71d60c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone LC-ESI-QTOF , positive-QTOFsplash10-0a4j-9700000000-f449a02b54e66ae754392017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 20V, Positive-QTOFsplash10-014i-0900000000-bc8358eb2ab225dea4902021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 50V, Positive-QTOFsplash10-0a4j-9700000000-f449a02b54e66ae754392021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 40V, Positive-QTOFsplash10-0btd-7900000000-7209912290de3f71d60c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 30V, Positive-QTOFsplash10-092a-4900000000-9ecbc817bebd6b19e66d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 10V, Positive-QTOFsplash10-014i-0900000000-7b2779bb29dca9d02c672021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Dihydrojasmone 20V, Positive-QTOFsplash10-014i-0900000000-05d13aeec0ec1585b4fa2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 10V, Positive-QTOFsplash10-014i-1900000000-cfff3babc03fd49562662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 20V, Positive-QTOFsplash10-0lk9-9800000000-83285acb7cf1e34487072016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 40V, Positive-QTOFsplash10-0zfu-9100000000-e64759fbf9737c9a27412016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 10V, Negative-QTOFsplash10-014i-0900000000-55dfd8185695db67befc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 20V, Negative-QTOFsplash10-014i-0900000000-e4378c3a759e06116abb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 40V, Negative-QTOFsplash10-0007-9800000000-776594568a877666eaf32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 10V, Negative-QTOFsplash10-014i-0900000000-05af9fd30de6fd63473b2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 20V, Negative-QTOFsplash10-014i-0900000000-b8664fb1978ed375317f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 40V, Negative-QTOFsplash10-0904-5900000000-27e60aa0dd222c4436352021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 10V, Positive-QTOFsplash10-096u-8900000000-8efb9f0e908dc9d97b822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 20V, Positive-QTOFsplash10-052f-9200000000-515a2a4da1b28748c2ac2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Dihydrojasmone 40V, Positive-QTOFsplash10-0536-9100000000-93cd3d88fe8a012ace902021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB008180
KNApSAcK IDC00055303
Chemspider ID56166
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydrojasmone
METLIN IDNot Available
PubChem Compound62378
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakashita Y, Hesse M: Conversion of nitroheptane to dihydrojasmone. Planta Med. 1985 Aug;51(4):349-50. [PubMed:17340535 ]
  2. Trost BM, Pinkerton AB: A three-component coupling approach to cyclopentanoids. J Org Chem. 2001 Nov 16;66(23):7714-22. [PubMed:11701026 ]
  3. Katsure J, Matsui M: Synthetic studies on cyclopentane derivatives. Pt. 1. Alternative routes to dl-prostaglandin-B1 and dihydrojasmone. Agric Biol Chem. 1969;33(7):1078-86. [PubMed:12262299 ]
  4. Bakuzis P, Bakuzis ML: Synthesis of 2-alkylcyclopentenones. Jasmone, dihydrojasmone, and a prostaglandin precursor. J Org Chem. 1977 Jul 8;42(14):2362-5. [PubMed:874613 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .