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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 19:40:54 UTC
Update Date2021-09-14 15:47:52 UTC
HMDB IDHMDB0006254
Secondary Accession Numbers
  • HMDB06254
Metabolite Identification
Common Name4-Hydroxyretinoic acid
Description4-Hydroxyretinoic acid belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof. Based on a literature review a significant number of articles have been published on 4-Hydroxyretinoic acid.
Structure
Thumb
Synonyms
Chemical FormulaC20H28O3
Average Molecular Weight316.4345
Monoisotopic Molecular Weight316.203844762
IUPAC Name(2E,4E,6E,8E)-9-(3-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenoic acid
Traditional Name4-hydroxyretinoic acid
CAS Registry Number66592-72-1
SMILES
C\C(\C=C\C1=C(C)C(O)CCC1(C)C)=C/C=C/C(/C)=C/C(O)=O
InChI Identifier
InChI=1S/C20H28O3/c1-14(7-6-8-15(2)13-19(22)23)9-10-17-16(3)18(21)11-12-20(17,4)5/h6-10,13,18,21H,11-12H2,1-5H3,(H,22,23)/b8-6+,10-9+,14-7+,15-13+
InChI KeyKGUMXGDKXYTTEY-FRCNGJHJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Retinoic acid
  • Diterpenoid
  • Retinoid skeleton
  • Medium-chain fatty acid
  • Branched fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
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
  • Nucleus
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023862
KNApSAcK IDNot Available
Chemspider ID4943093
KEGG Compound IDC16677
BioCyc IDNot Available
BiGG ID2299866
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6438629
PDB IDNot Available
ChEBI ID63795
Food Biomarker OntologyNot Available
VMH IDCE2956
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRosenberger, Michael. Retinoic acid metabolites. 1. Total synthesis of 4-hydroxy- and 4-oxoretinoic acid. Journal of Organic Chemistry (1982), 47(9), 1698-701.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Napoli JL, Posch KP, Fiorella PD, Boerman MH: Physiological occurrence, biosynthesis and metabolism of retinoic acid: evidence for roles of cellular retinol-binding protein (CRBP) and cellular retinoic acid-binding protein (CRABP) in the pathway of retinoic acid homeostasis. Biomed Pharmacother. 1991;45(4-5):131-43. [PubMed:1932598 ]
  2. Roberts ES, Vaz AD, Coon MJ: Role of isozymes of rabbit microsomal cytochrome P-450 in the metabolism of retinoic acid, retinol, and retinal. Mol Pharmacol. 1992 Feb;41(2):427-33. [PubMed:1538719 ]
  3. Spear PA, Garcin H, Narbonne JF: Increased retinoic acid metabolism following 3,3',4,4',5,5'-hexabromobiphenyl injection. Can J Physiol Pharmacol. 1988 Sep;66(9):1181-6. [PubMed:2851384 ]