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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.)

functional group

ester

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).[1] 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.[2]
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBP6797V
MKBD3852
43997PJ
04121BJ
17203PI

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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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