Tryptophol

Base Information

• Chemical Name: Tryptophol
• CAS No.: 526-55-6
• Molecular Formula: C10H11NO
• Molecular Weight: 161.203
• Hs Code.: 29339990
• European Community (EC) Number: 208-393-2
• NSC Number: 3884
• UNII: 5809LZ7G1U
• DSSTox Substance ID: DTXSID2060173
• Nikkaji Number: J6.661C
• Wikipedia: Tryptophol
• Wikidata: Q5479351
• Metabolomics Workbench ID: 38334
• ChEMBL ID: CHEMBL226545
• Mol file: 526-55-6.mol

Synonyms:1H-indole-3-ethanol;3-indolylethanol;indole-3-ethanol;tryptophol;tryptophol acetate

Chemical Property of Tryptophol

Chemical Property:

• Appearance/Colour: off-white to brown crystalline mass
• Vapor Pressure: 9.66E-06mmHg at 25°C
• Melting Point: 56-59 °C(lit.)
• Refractive Index: 1.674
• Boiling Point: 357.803 °C at 760 mmHg
• PKA: 15.16±0.10(Predicted)
• Flash Point: 170.193 °C
• PSA: 36.02000
• Density: 1.219 g/cm³
• LogP: 1.70270
• Storage Temp.: 2-8°C
• Solubility.: methanol: 0.1 g/mL, clear
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 161.084063974
• Heavy Atom Count: 12
• Complexity: 149

Purity/Quality:

99% ^*data from raw suppliers

Tryptophol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 24/25:
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Amino Acids and Derivatives
• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCO
• Uses: Tryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation. Reactant for preparation of:Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activitiesAnti-HIV-1 agentsInhibitors of Protein-Protein InteractionsPartial agonists of the serotonin 5-HT1A receptorGrowth hormone secretagoguesVascular endothelial growth factor (VEGF) inhibitorsA2B adenosine receptor ligandsPotential detoxification inhibitors of the crucifer phytoalexin brassininInhibitors of interleukine 6Dual binding site acetylcholinesterase inhibitors

Technology Process of Tryptophol

There total 62 articles about Tryptophol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

indole-3-acetic acid (87-51-4) → 2-(3-indole)-ethanol (526-55-6,930395-07-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Reflux;

Reference yield: 100.0%

2-(3-indolyl)oxoacetic acid methyl ester (18372-22-0) → 2-(3-indole)-ethanol (526-55-6,930395-07-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1039/b610497e

Reference yield: 98.0%

3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole (101079-48-5) → 2-(3-indole)-ethanol (526-55-6,930395-07-6)

Guidance literature:

With aluminium(III) chloride hexahydrate; In methanol; at 100 ℃; for 0.25h; Solvent; Temperature; chemoselective reaction; Microwave irradiation; Sealed tube;

DOI:10.1080/00397911.2013.851243

upstream raw materials:

indole-3-acetic acid

Indole-3-acetic acid methyl ester

ethyl 3-indoleacetate

methanol

Downstream raw materials:

3-Methyl-2,3,4',5'-tetrahydrofurano<2',3':2,3>indol

3-(2-bromoethyl)-1H-indole

indole-3-acetic acid

3-(2-chloroethyl)indole

Refernces

• 1、 Suvorov,Buyanov. "-". . . Retrieved 1970.
• 2、 -. "S -indole benzamide derivative as well as preparation method and application thereof". Paragraph 0030; 0034-0036. . Retrieved 2021/09/15.
• 3、 -. "AZEPINO-INDOLES AND OTHER HETEROCYCLES FOR TREATING BRAIN DISORDERS". Paragraph 0203. . Retrieved 2020/09/12.