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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:50:07 UTC
Update Date2023-02-21 17:22:16 UTC
HMDB IDHMDB0032498
Secondary Accession Numbers
  • HMDB32498
Metabolite Identification
Common NamePseudoionone
DescriptionPseudoionone (CAS: 141-10-6), also known as citrylideneacetone or psi-ionone, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Pseudoionone is an extremely weak basic (essentially neutral) compound (based on its pKa). Pseudoionone is a sweet, balsamic, and citrus tasting compound. Outside of the human body, pseudoionone has been detected, but not quantified in, a few different foods, such as cherry tomato and garden tomato. This could make pseudoionone a potential biomarker for the consumption of these foods. Pseudoionone is used as a food additive (EAFUS: Everything Added to Food in the United States).
Structure
Data?1677000136
Synonyms
ValueSource
(3E,5E)-6,10-Dimethylundeca-3,5,9-trien-2-oneChEBI
2,6-Dimethylundeca-2,6,8-triene-10-oneChEBI
6,10-Dimethyl-3,5,9-undecatrien-2-oneChEBI
6,10-Dimethyl-3,5,9-undecatriene-2-oneChEBI
CitrylideneacetoneChEBI
(3E,5E)-6,10-Dimethyl-3,5,9-undecatrien-2-oneHMDB
.psi.-iononeHMDB
2,6-Dimethyl hendeca-2,6,8-trien-10-oneHMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #1HMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #2HMDB
3,5,9-Undecatrien-2-one, 6,10-dimethyl, #3HMDB
6,10-Dimethyl-(e,e)-3,5,9-undecatrien-2-oneHMDB
6,10-Dimethylundeca-3,5,9-trien-2-oneHMDB
8-[N-aziridylethylamino]-2,6-Dimethyloctene-2HMDB
laquo psiraquo -IononeHMDB
N-[2-(1-Aziridinyl)ethyl]-3,7-dimethyl-6-octen-1-amineHMDB
PseudoiononesHMDB
psi-IononeHMDB
trans-.psi.-iononeHMDB
(E,E)-6,10-Dimethyl-3,5,9-undecatrien-2-oneHMDB
(E,E)-PseudoiononeHMDB
(all-E)-psi-IononeHMDB
(all-E)-ψ-IononeHMDB
2,6-Dimethyl-2,6,8-undecatrien-10-oneHMDB
2,6-Dimethylhendeca-2,6,8-trien-10-oneHMDB
2-PseudoiononeHMDB
2-PseudojononHMDB
3E,5E-PseudoiononeHMDB
PseudoiononeHMDB
phi-IononeHMDB
trans,trans-PseudoiononeHMDB
trans-psi-IononeHMDB
trans-ψ-IononeHMDB
φ-IononeHMDB
ψ-IononeHMDB
Chemical FormulaC13H20O
Average Molecular Weight192.2973
Monoisotopic Molecular Weight192.151415262
IUPAC Name(3E,5E)-6,10-dimethylundeca-3,5,9-trien-2-one
Traditional Namepseudoionone
CAS Registry Number3548-78-5
SMILES
CC(C)=CCC\C(C)=C\C=C\C(C)=O
InChI Identifier
InChI=1S/C13H20O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h6-7,9-10H,5,8H2,1-4H3/b10-6+,12-9+
InChI KeyJXJIQCXXJGRKRJ-KOOBJXAQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.079 g/LALOGPS
logP4.57ALOGPS
logP3.68ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)19.73ChemAxon
pKa (Strongest Basic)-4.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.92 m³·mol⁻¹ChemAxon
Polarizability24.22 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+150.53930932474
DeepCCS[M-H]-147.88430932474
DeepCCS[M-2H]-183.80430932474
DeepCCS[M+Na]+159.39630932474
AllCCS[M+H]+147.932859911
AllCCS[M+H-H2O]+144.032859911
AllCCS[M+NH4]+151.532859911
AllCCS[M+Na]+152.532859911
AllCCS[M-H]-148.032859911
AllCCS[M+Na-2H]-149.232859911
AllCCS[M+HCOO]-150.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
PseudoiononeCC(C)=CCC\C(C)=C\C=C\C(C)=O1976.7Standard polar33892256
PseudoiononeCC(C)=CCC\C(C)=C\C=C\C(C)=O1524.2Standard non polar33892256
PseudoiononeCC(C)=CCC\C(C)=C\C=C\C(C)=O1577.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Pseudoionone,1TMS,isomer #1C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C1688.7Semi standard non polar33892256
Pseudoionone,1TMS,isomer #1C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C1668.2Standard non polar33892256
Pseudoionone,1TBDMS,isomer #1C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C1917.0Semi standard non polar33892256
Pseudoionone,1TBDMS,isomer #1C=C(/C=C/C=C(\C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C1883.4Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoionone GC-MS (Non-derivatized) - 70eV, Positivesplash10-05mo-9500000000-88a840082ecbb350c6a62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Pseudoionone 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 - Pseudoionone 10V, Positive-QTOFsplash10-002f-0900000000-2db17f4b4c990b9823412016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 20V, Positive-QTOFsplash10-00pu-4900000000-52ad299b7419d9c485192016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 40V, Positive-QTOFsplash10-0gb9-9200000000-2d38b7ef565b063e02a12016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 10V, Negative-QTOFsplash10-0006-0900000000-32871f26fdd2d0019cb52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 20V, Negative-QTOFsplash10-0006-0900000000-575b176dca9d2bf2b4cb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 40V, Negative-QTOFsplash10-0a6u-4900000000-19449ebc8c2cc7ea297d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 10V, Negative-QTOFsplash10-0006-0900000000-982b69b98355bf67bf412021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 20V, Negative-QTOFsplash10-0a4l-4900000000-715808bcaeeaf260c1812021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 40V, Negative-QTOFsplash10-0aor-5900000000-7fc4257f2401238154ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 10V, Positive-QTOFsplash10-00l6-9800000000-0f5de46efabff5d3d2ff2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 20V, Positive-QTOFsplash10-05qc-9200000000-8a02cf4811e6304593e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Pseudoionone 40V, Positive-QTOFsplash10-0006-9200000000-a6eda7fe87b35637f77c2021-09-24Wishart 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
  • 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 IDFDB010156
KNApSAcK IDNot Available
Chemspider ID1387980
KEGG Compound IDNot Available
BioCyc IDCPD-13371
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound1757003
PDB IDNot Available
ChEBI ID67207
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. 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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.