Record Information
Version1.0
Creation date2015-10-09 22:31:07 UTC
Update date2017-01-19 02:36:26 UTC
FoodComEx IDPC000515
FoodDB RecordFDB022711
Chemical Information
Name5-Hydroxytryptophol
Description5-Hydroxytryptophol is a relatively minor metabolite of serotonin that is excreted primarily as the glucuronide conjugate in human urine. 5-Hydroxytryptophol becomes more important quantitatively during alcohol intoxication, when a shift in the metabolism of serotonin occurs from 5-hydroxyindole acetic acid toward increased (15-fold higher) formation of 5-hydroxytryptophol due to the inhibition of aldehyde dehydrogenase by ethanol-derived acetaldehyde. Urinary excretion of 5-hydroxytryptophol has also been shown to be markedly increased for several hours following intake of foods rich in serotonin, such as bananas. Wide interspecies variation has been reported in the metabolism serotonin to 5-hydroxytryptophol; 5-Hydroxytryptophol makes up 35% of the excreted serotonin metabolites in the rat on average and 10 to 20% in several other species. Human UDP-glucuronosyltransferase 1A6 (UGT1A6) plays a predominant role in the glucuronidation of 5-hydroxytryptophol by human liver microsomes. (PMID 15258112) [HMDB]. 5-Hydroxytryptophol is found in many foods, some of which are climbing bean, macadamia nut (m. tetraphylla), pepper (c. frutescens), and scarlet bean.
CAS Number154-02-9
Structure
Thumb
Synonyms
SynonymSource
5-HTOLhmdb
5-Hydroxy-1H-indole-3-ethanolhmdb
5-Hydroxy-1H-Indole-3-ethanol(9CI)hmdb
5-hydroxy-3-indolehmdb
5-hydroxy-indole-acetic acidhmdb
5-hydroxyindoacetic acidhmdb
5-hydroxyindolhmdb
5-hydroxyindolacetatehmdb
5-hydroxyindolacetate acidhmdb
5-Hydroxyindole-3-ethanolhmdb
5-hydroxyindole-acetic acidhmdb
5-Hydroxytryptopholhmdb
Hydroxytryptopholhmdb
Chemical FormulaC10H11NO2
IUPAC name3-(2-hydroxyethyl)-1H-indol-5-ol
InChI IdentifierInChI=1S/C10H11NO2/c12-4-3-7-6-11-10-2-1-8(13)5-9(7)10/h1-2,5-6,11-13H,3-4H2
InChI KeyKQROHCSYOGBQGJ-UHFFFAOYSA-N
Isomeric SMILESOCCC1=CNC2=CC=C(O)C=C12
Average Molecular Weight177.1998
Monoisotopic Molecular Weight177.078978601
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Hydroxyindole
  • Indole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 5 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci Z4206
Cayman Chemical 16114
Toronto Research Chemicals H976000