1125-40-2

Basic information

• Product Name: 5-HYDROXY-3-METHYLINDOLE
• Synonyms: 5-HYDROXY-3-METHYLINDOLE;3-Methyl-1H-indol-5-ol
• CAS NO: 1125-40-2
• Molecular Formula: C₉H₉NO
• Molecular Weight: 147.17386
• EINECS: 200-589-5
• Mol File: 1125-40-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 114-115℃
• Boiling Point: 344.8 °C at 760 mmHg
• Flash Point: 162.3 °C
• Appearance: /
• Density: 1.262
• Vapor Pressure: 3.23E-05mmHg at 25°C
• Refractive Index: 1.703
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 10.17±0.40(Predicted)
• CAS DataBase Reference: 5-HYDROXY-3-METHYLINDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-HYDROXY-3-METHYLINDOLE(1125-40-2)
• EPA Substance Registry System: 5-HYDROXY-3-METHYLINDOLE(1125-40-2)

Safety Data

• Hazardous Substances Data: 1125-40-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 27, p. 4565, 1986 DOI: 10.1016/S0040-4039(00)85004-2

InChI:InChI=1/C9H9NO/c1-6-5-10-9-3-2-7(11)4-8(6)9/h2-5,10-11H,1H3

Upstream product

• 83-34-1 3-Methylindole 
• 1453-97-0 5-benzyloxygramine 
• 99777-70-5 3-methyl-1-(phenylamino)-1H-indol-5-ol 
• 1049971-33-6 2-(β-amino-isopropyl)-hydroquinone 
• 21987-24-6 5-(benzyloxy)-3-methyl-1H-indole 
• 51145-58-5 [4-(benzyloxy)phenyl]hydrazine 
• 224635-64-7 5-hydroxy-3-methyl-3H-benzofuran-2-one 
• 224635-68-1 2-(2,5-dihydroxy-phenyl)-propionamide 
• 130570-61-5 1-[(5'-benzyloxy-2'-nitro)phenyl]-2-cyanopropane 
• 21987-25-7 5-methoxy-3-methyl-1H-indole 
• 67-56-1 methanol 
• 1953-54-4 indol-5-ol 

Relevant articles and documents

Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry

Sulfatases hydrolyze sulfated metabolites to their corresponding alcohols and are present in all domains of life. These enzymes have found major application in metabolic investigation of drugs, doping control analysis and recently in metabolomics. Interest in sulfatases has increased due to a link between metabolic processes involving sulfated metabolites and pathophysiological conditions in humans. Herein, we present the first comprehensive substrate specificity and kinetic analysis of the most commonly used arylsulfatase extracted from the snail Helix pomatia. In the past, this enzyme has been used in the form of a crude mixture of enzymes, however, recently we have purified this sulfatase for a new application in metabolomics-driven discovery of sulfated metabolites. To evaluate the substrate specificity of this promiscuous sulfatase, we have synthesized a series of new sulfated metabolites of diverse structure and employed a mass spectrometric assay for kinetic substrate hydrolysis evaluation. Our analysis of the purified enzyme revealed that the sulfatase has a strong preference for metabolites with a bi- or tricyclic aromatic scaffold and to a lesser extent for monocyclic aromatic phenols. This metabolite library and mass spectrometric method can be applied for the characterization of other sulfatases from humans and gut microbiota to investigate their involvement in disease development.

Design and synthesis of a novel series of [1-(4-hydroxy-benzyl)-1H-indol-5-yloxy]-acetic acid compounds as potent, selective, thyroid hormone receptor β agonists

The design, synthesis, and structure activity relationships for a novel series of indoles as potent, selective, thyroid hormone receptor β (TRβ) agonists is described. Compounds with >50× binding selectivity for TRβ over TRα were generated and evaluation of compound 1c from this series in a model of dyslipidemia demonstrated positive effects on plasma lipid endpoints in vivo.

Fast deprotection of phenoxy benzyl ethers in transfer hydrogenation assisted by microwave

Phenoxy benzyl ethers are easily and quickly deprotected in the presence of ammonium formate and microencapsulated Pd(0)EnCat with the assistance of microwave irradiation. This procedure can be applied in the presence of other functional groups as well. The described protocol is particularly convenient for the preparation in a parallel and automatic fashion of libraries of compounds possessing a phenol type moiety.