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246298

Sigma-Aldrich

4-Methoxyindole

99%

Empirical Formula (Hill Notation):
C9H9NO
CAS Number:
Molecular Weight:
147.17
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

99%

form

powder

bp

181-183 °C/24 mmHg (lit.)

mp

69-70 °C (lit.)

solubility

ethanol: 50 mg/mL, clear, faintly yellow

SMILES string

COc1cccc2[nH]ccc12

InChI

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

InChI key

LUNOXNMCFPFPMO-UHFFFAOYSA-N

Application

Reactant for preparation of:
  • GABA analogs
  • Sodium-Dependent Glucose Co-transporter 2 (SGLT2) Inhibitors for the Management of Hyperglycemia in Diabetes
  • Anticancer agents
  • Integrase strand-transfer inhibitors (INSTIs)
  • Inhibitor of Proliferation of Colon Cancer Cells
  • Isomeridianin G as GSK-3ß inhibitors
  • HIV-1 integrase inhibitors
  • Inhibitors of mitogen activated protein kinase-activated protein kinase 2 (MK-2)
4-Methoxyindole was used for comparing the complexation reaction of β-cyclodextrin (β-CD) with pindolol using reversed-phase liquid chromatography.

Packaging

1 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Certificate of Origin

Carmen Gazpio et al.
Journal of pharmaceutical and biomedical analysis, 37(3), 487-492 (2005-03-03)
The complexation with beta-cyclodextrin (beta-CD) has been investigated using reversed-phase liquid chromatography. The compounds tested have been pindolol and, for comparison purposes, indole and 4-methoxyindole. The retention behaviour has been analysed on a Kromasil 100 C18 column and the mobile
Brenden Barco et al.
Frontiers in plant science, 10, 1775-1775 (2020-02-23)
The plant kingdom produces hundreds of thousands of specialized bioactive metabolites, some with pharmaceutical and biotechnological importance. Their biosynthesis and function have been studied for decades, but comparatively less is known about how transcription factors with overlapping functions and contrasting
Brenden Barco et al.
Nature communications, 10(1), 3444-3444 (2019-08-03)
Plants synthesize numerous ecologically specialized, lineage-specific metabolites through biosynthetic gene duplication and functional specialization. However, it remains unclear how duplicated genes are wired into existing regulatory networks. We show that the duplicated gene CYP82C2 has been recruited into the WRKY33 regulon
Thomas Heine et al.
Applied biochemistry and biotechnology, 181(4), 1590-1610 (2016-11-11)
The enantioselective epoxidation of styrene and related compounds by two-component styrene monooxygenases (SMOs) has targeted these enzymes for development as biocatalysts. In the present work, we prepare genetically engineered fusion proteins that join the C-terminus of the epoxidase (StyA) to
Jung Min Song et al.
International journal of pharmaceutics, 477(1-2), 96-101 (2014-10-15)
Indole-3-carbinol (I3C), a constituent of commonly consumed Brassica vegetables, has been shown to have anticancer effects in a variety of preclinical models of lung cancer. However, it has shown only limited efficacy in clinical trials, likely due to its poor

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