You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
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, also known as fema 3763 or jasmone,dihydro, 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrojasmone is an aroma compound with the chemical formula C11H18O. Dihydrojasmone is a fresh, herbal, and jasmin tasting compound. Outside of the human body, Dihydrojasmone has been detected, but not quantified in, citrus. This could make dihydrojasmone a potential biomarker for the consumption of these foods. Dihydrojasmone belongs to the family of ketones. It has a fruity, jasmine odor with woody and herbal undertones. Perfumery uses include natural green, woody, lavender and bergamot.
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
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

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.77 g/LALOGPS
logP3.55ALOGPS
logP3.46ChemAxon
logS-2.3ALOGPS
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
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0iml-9400000000-a9ad6584e7f14ccde4f3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02hj-9700000000-fbe45b6deff4c436a788Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-7900000000-79a7d490f28c7bc92c64Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ikc-7900000000-c07ace9e4f88c96f29cfSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0iml-9400000000-a9ad6584e7f14ccde4f3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-02hj-9700000000-fbe45b6deff4c436a788Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-7900000000-79a7d490f28c7bc92c64Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ikc-7900000000-c07ace9e4f88c96f29cfSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9700000000-6b8a4052589c5f46caeeSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-7b2779bb29dca9d02c67Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-014i-0900000000-05d13aeec0ec1585b4faSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-092a-4900000000-9ecbc817bebd6b19e66dSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0btd-7900000000-7209912290de3f71d60cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4j-9700000000-f449a02b54e66ae75439Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1900000000-cfff3babc03fd4956266Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0lk9-9800000000-83285acb7cf1e3448707Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfu-9100000000-e64759fbf9737c9a2741Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-55dfd8185695db67befcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0900000000-e4378c3a759e06116abbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9800000000-776594568a877666eaf3Spectrum
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 IDNot Available
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
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Trost BM, Pinkerton AB: A three-component coupling approach to cyclopentanoids. J Org Chem. 2001 Nov 16;66(23):7714-22. [PubMed:11701026 ]
  2. Nakashita Y, Hesse M: Conversion of nitroheptane to dihydrojasmone. Planta Med. 1985 Aug;51(4):349-50. [PubMed:17340535 ]
  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.. .