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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:59:50 UTC
Update Date2023-02-21 17:25:29 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
Thumb
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
Physiological effectNot Available
Disposition
Process
Role
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
Predicted Chromatographic Properties
Spectra
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.