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365572

Sigma-Aldrich

Methyl 6-methoxy-2-indolecarboxylate

99%

Synonym(s):

2-Methoxycarbonyl-6-methoxyindole, 6-Methoxyindole-2-carboxylic acid methyl ester

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About This Item

Empirical Formula (Hill Notation):
C11H11NO3
CAS Number:
98081-83-5
Molecular Weight:
205.21
MDL number:
MFCD00134301
UNSPSC Code:
12352100
PubChem Substance ID:
24862540
NACRES:
NA.22

Assay

99%

mp

117-119 °C (lit.)

SMILES string

COC(=O)c1cc2ccc(OC)cc2[nH]1

InChI

1S/C11H11NO3/c1-14-8-4-3-7-5-10(11(13)15-2)12-9(7)6-8/h3-6,12H,1-2H3

InChI key

OPUUCOLVBDQWEY-UHFFFAOYSA-N

Application

Methyl 6-methoxy-2-indolecarboxylate is suitable for use in the production of dyes by Escherichia coli expressing naphthalene dioxygenase (NDO) and toluene dioxygenase (TDO). It is also suitable for use in the production of dyes by Escherichia coli expressing multicomponent phenol hydroxylase (mPH) from Pseudomonas sp. strains KL33 and KL28.
Reactant for preparation of:
  • Benzoxazole containing indole analogs as peroxisome proliferator-activated receptor-γ/δ dual agonists
  • Potent antiproliferative agent against human leukemia K562 cells
  • Indole-indolone scaffold via [3+2] annulation of arynes
  • Latonduine derivatives via intramolecular Heck reaction as possible anticancer agents
  • Arylthioindoles as potent inhibitors of tubulin polymerization
  • Heterocycle-fused derivatives of 1-oxo-1,2,3,4-tetrahydropyrazine via Ugi condensation
  • Indole fatty alcohols (IFAs) as promoters of differentiation of neural stem cell derived neurospheres into neurons. Potential application for treatment of neurodegenerative diseases
  • Light-dependent tumor necrosis factor-α antagonists
  • 2-substituted indole melatonin receptor ligands

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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J Y Kim et al.
Letters in applied microbiology, 36(6), 343-348 (2003-05-20)
To isolate and characterize the phorate [O,O-diethyl-S-(ethylthio)methyl phosphoradiothioate] degrading bacteria from agricultural soil, and their assessment for multifarious biological activities of environmental and agronomic significance. Based on their morphological and biochemical characteristics, the selected isolates PS-1, PS-2 and PS-3 were
J Y Kim et al.
Letters in applied microbiology, 41(2), 163-168 (2005-07-22)
To establish multicomponent phenol hydroxylases (mPHs) as novel biocatalysts for producing dyestuffs and hydroxyindoles such as 7-hydroxyindole (7-HI) from indole and its derivatives. We have isolated Pseudomonas sp. KL33, which possesses a phenol degradation pathway similar to that found in

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