Tryptophol

Tryptophol Basic information
Product Name:Tryptophol
Synonyms:INDOLE-3-ETHANOL;B-3-INDOLEETHANOL;B-3-INDOLYLETHANOL;BETA-3-INDOLYLETHANOL;3-(BETA-HYDROXYETHYL)INDOLE;3-INDOLEETHANOL;2-(1H-INDOL-3-YL)ETHAN-1-OL;2-(1H-INDOL-3-YL)-ETHANOL
CAS:526-55-6
MF:C10H11NO
MW:161.2
EINECS:208-393-2
Product Categories:Heterocyclic Compounds;Indoles;Simple Indoles;Intermediate
Mol File:526-55-6.mol
Tryptophol Structure
Tryptophol Chemical Properties
Melting point 56-59 °C(lit.)
Boiling point 174 °C (2.02527 mmHg)
density 1.0840 (rough estimate)
refractive index 1.5200 (estimate)
Fp 255 °C
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility methanol: 0.1 g/mL, clear
pka15.16±0.10(Predicted)
form Crystalline Mass, Crystals, Flakes or Powder
color Off-white to brown
Water Solubility 10 g/L (20 ºC)
Merck 14,9798
BRN 125553
InChIKeyMBBOMCVGYCRMEA-UHFFFAOYSA-N
LogP1.280 (est)
CAS DataBase Reference526-55-6(CAS DataBase Reference)
NIST Chemistry Reference1H-indole-3-ethanol(526-55-6)
EPA Substance Registry System1H-Indole-3-ethanol (526-55-6)
Safety Information
Hazard Codes Xi
Safety Statements 24/25
WGK Germany 3
RTECS KL3685000
8
Hazard Note Irritant
TSCA Yes
HS Code 29339990
ToxicityLD50 intraperitoneal in mouse: 351mg/kg
MSDS Information
ProviderLanguage
3-(2-Hydroxyethyl)indole English
SigmaAldrich English
ACROS English
ALFA English
Tryptophol Usage And Synthesis
Chemical Propertiesoff-white to brown crystalline mass, crystals,
UsesTryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation.
UsesReactant for preparation of:
  • Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activities
  • Anti-HIV-1 agents
  • Inhibitors of Protein-Protein Interactions
  • Partial agonists of the serotonin 5-HT1A receptor
  • Growth hormone secretagogues
  • Vascular endothelial growth factor (VEGF) inhibitors
  • A2B adenosine receptor ligands
  • Potential detoxification inhibitors of the crucifer phytoalexin brassinin
  • Inhibitors of interleukine 6
  • Dual binding site acetylcholinesterase inhibitors
DefinitionChEBI: An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.
Synthesis Reference(s)Canadian Journal of Chemistry, 42, p. 485, 1964 DOI: 10.1139/v64-070
Purification MethodsCrystallise it from diethyl ether/pet ether, *C6H6, *C6H6/pet ether. The picrate has m 100-101o (from *C6H6). [Beilstein 21 I 218, 21 II 49, 21 III/IV 788, 21/3 V 61.]
Tryptophol Indometacin Ethanol Methyl 2-hydroxyethyl cellulose Indole-3-butyric acid 2-(2-Aminoethylamino)ethanol Oxindole Hydroxyethyl Cellulose Hydroxyethyl starch 5-BENZYLOXYINDOLE-3-ACETIC ACID 2-(METHYLSULFONYL)ETHANOL 5-HYDROXYINDOLE-3-ACETIC ACID Sodium isethionate Indole 5-METHYLINDOLE-3-ACETIC ACID METHYL 3-INDOLYLACETATE Indole-3-acetic acid PIPERACETAZINE (250 MG)

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