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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:59:50 UTC
Update Date2021-09-14 14:57:11 UTC
HMDB IDHMDB0036821
Secondary Accession Numbers
  • HMDB36821
Metabolite Identification
Common Name3-Hydroxy-beta-ionone
Description3-Hydroxy-beta-ionone (CAS: 116296-75-4), also known as apo-9-zeaxanthinone (CAS: 50281-38-4), belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-Hydroxy-beta-ionone has been detected, but not quantified in, several different foods, such as green bell peppers, red bell peppers, pepper (C. annuum), Italian sweet red peppers, and orange bell peppers. This could make 3-hydroxy-beta-ionone a potential biomarker for the consumption of these foods. 3-Hydroxy-beta-ionone is found in pulses. 3-Hydroxy-beta-ionone is isolated from Phaseolus vulgaris (kidney bean).
Structure
Data?1594137272
Synonyms
ValueSource
3-Hydroxy-b-iononeGenerator
3-Hydroxy-β-iononeGenerator
(3E)-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-oneHMDB
(3E)-4-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-oneHMDB
(3R)-3-Hydroxy-beta-iononeHMDB
(3R)-3-Hydroxy-β-iononeHMDB
(R)-(-)-3-Hydroxy-beta-iononeHMDB
(R)-(-)-3-Hydroxy-β-iononeHMDB
(R)-3-Hydroxy-beta-iononeHMDB
(R)-3-Hydroxy-β-iononeHMDB
3beta-Hydroxymegastigma-5,7-dien-9-oneHMDB
3Β-hydroxymegastigma-5,7-dien-9-oneHMDB
Apo-9-zeaxanthinoneHMDB
3-Hydroxy-beta-iononeHMDB
Chemical FormulaC13H20O2
Average Molecular Weight208.2967
Monoisotopic Molecular Weight208.146329884
IUPAC Name(3E)-4-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]but-3-en-2-one
Traditional Name(3R)-hydroxy-β-ionone
CAS Registry Number50281-38-4
SMILES
CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C
InChI Identifier
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1
InChI KeyHFRZSVYKDDZRQY-MVIFTORASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Megastigmane sesquiterpenoid
  • Cyclofarsesane sesquiterpenoid
  • Ionone derivative
  • Acryloyl-group
  • Enone
  • Alpha,beta-unsaturated ketone
  • Secondary alcohol
  • Ketone
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

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 Solubility0.73 g/LALOGPS
logP10(2.1) g/LALOGPS
logP10(1.89) g/LChemAxon
logS10(-2.5) g/LALOGPS
pKa (Strongest Acidic)18.91ChemAxon
pKa (Strongest Basic)-1.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity63.49 m³·mol⁻¹ChemAxon
Polarizability24.05 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
DeepCCS[M+H]+158.57130932474
DeepCCS[M-H]-156.17630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-beta-iononeCC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C2570.5Standard polar33892256
3-Hydroxy-beta-iononeCC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C1621.0Standard non polar33892256
3-Hydroxy-beta-iononeCC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C1683.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-beta-ionone,1TMS,isomer #1CC(=O)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C1773.8Semi standard non polar33892256
3-Hydroxy-beta-ionone,1TMS,isomer #2C=C(/C=C/C1=C(C)C[C@@H](O)CC1(C)C)O[Si](C)(C)C1824.9Semi standard non polar33892256
3-Hydroxy-beta-ionone,2TMS,isomer #1C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C1846.5Semi standard non polar33892256
3-Hydroxy-beta-ionone,2TMS,isomer #1C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C1942.2Standard non polar33892256
3-Hydroxy-beta-ionone,1TBDMS,isomer #1CC(=O)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C2000.0Semi standard non polar33892256
3-Hydroxy-beta-ionone,1TBDMS,isomer #2C=C(/C=C/C1=C(C)C[C@@H](O)CC1(C)C)O[Si](C)(C)C(C)(C)C2065.8Semi standard non polar33892256
3-Hydroxy-beta-ionone,2TBDMS,isomer #1C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C2313.1Semi standard non polar33892256
3-Hydroxy-beta-ionone,2TBDMS,isomer #1C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C2438.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-beta-ionone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-beta-ionone 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 - 3-Hydroxy-beta-ionone 10V, Negative-QTOFsplash10-0a4i-0390000000-4dfd440e0b9531f8a7572016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Negative-QTOFsplash10-0a4r-1960000000-fd1b133f482bc7573abe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Negative-QTOFsplash10-01ox-2900000000-04eff6259412f3590daf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Negative-QTOFsplash10-0a4i-0090000000-43a9bdbf7663e467c30d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Negative-QTOFsplash10-0a4s-0940000000-e8333249a633e6a768b92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Negative-QTOFsplash10-0002-1900000000-31fb706dd6e842a6860a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Positive-QTOFsplash10-052f-0920000000-ca4bc2d8536a477454bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Positive-QTOFsplash10-006x-1910000000-0800f9d35f89acbe67842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Positive-QTOFsplash10-0kft-6900000000-561c8ee7b8326d943c552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Positive-QTOFsplash10-0a4r-1930000000-362c8ff12dca214674b52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Positive-QTOFsplash10-0abc-4900000000-3c361104d4dd0ac028bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Positive-QTOFsplash10-0006-9800000000-626f2e38ffe2cc811bbe2021-09-24Wishart 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 IDFDB001764
KNApSAcK IDC00022191
Chemspider ID9302625
KEGG Compound IDNot Available
BioCyc IDCPD-7200
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11127505
PDB IDNot Available
ChEBI ID53173
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.