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284734

Sigma-Aldrich

Indole-3-carboxylic acid

ReagentPlus®, 99%

Synonym(s):

β-Indolylcarboxylic acid, 3-Carboxyindole, 3-Indole formic acid, 3-Indolylcarboxylic acid, Indole-β-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C9H7NO2
CAS Number:
771-50-6
Molecular Weight:
161.16
Beilstein/REAXYS Number:
129435
EC Number:
212-231-6
MDL number:
MFCD00005624
UNSPSC Code:
12352100
PubChem Substance ID:
24857174
NACRES:
NA.22

product line

ReagentPlus®

assay

99%

form

solid

mp

232-234 °C (dec.) (lit.)

solubility

95% ethanol: soluble 5%, clear to slightly hazy, light yellow to yellow

SMILES string

OC(=O)c1c[nH]c2ccccc12

InChI

1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)

InChI key

KMAKOBLIOCQGJP-UHFFFAOYSA-N

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General description

The structures of the derivatives of indole-3-carboxylic acid were studied using gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR).

Application

Reactant for preparation of:
  • Anticancer agents
  • Derivatives of amino acids and peptides
  • Serotonin 5-HT4 receptor antagonists
  • Primary acylureas
  • Inhibitors of Gli1-mediated transcription in the Hedgehog pathway
  • Serotonin 5-HT6 antagonists
  • Very Late Antigen-4 (VLA-4) sntagonists
  • EphB3 receptor tyrosine kinase inhibitors
  • Potential Therapeutic Agent for Alzheimer′s Disease
  • Vinyl ester pseudotripeptide proteasome inhibitors

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Vadim Shevyrin et al.
Forensic science international, 232(1-3), 1-10 (2013-09-24)
By means of gas chromatography with high resolution mass spectrometry (GC-HRMS), ultra-high performance liquid chromatography in combination with high resolution tandem mass spectrometry (UHPLC-HRMS), nuclear magnetic resonance spectroscopy (NMR) and Fourier transform infrared spectroscopy (FT-IR), structure of a series from
Toyokazu Yoshida et al.
Bioscience, biotechnology, and biochemistry, 66(11), 2388-2394 (2003-01-01)
After enrichment culture with indole-3-carboxylate in static culture, a novel reversible decarboxylase, indole-3-carboxylate decarboxylase, was found in Arthrobacter nicotianae FI1612 and several molds. The enzyme reaction was examined in resting-cell reactions with A. nicotianae FI1612. The enzyme activity was induced
J J Michnovicz et al.
Journal of the National Cancer Institute, 82(11), 947-949 (1990-06-06)
Dietary indoles in cruciferous vegetables induce cytochrome P450 enzymes and have prevented tumors in various animal models. Because estradiol metabolism is also cytochrome P450 mediated and linked to breast cancer risk, indoles may similarly reduce estrogen-responsive tumors in humans. We
Paweł Bednarek
Current opinion in plant biology, 15(4), 407-414 (2012-03-27)
In plants, a host's responses to an attempted infection include activation of various secondary metabolite pathways, some of which are specific for particular plant phylogenetic clades. Phytochemicals that represent respective end products in plant immunity have been stereotypically linked to
Mu-Yang Wang et al.
Journal of integrative plant biology, 54(7), 471-485 (2012-05-26)
Camalexin (3-thiazol-2'-yl-indole) is the major phytoalexin found in Arabidopsis thaliana. Several key intermediates and corresponding enzymes have been identified in camalexin biosynthesis through mutant screening and biochemical experiments. Camalexin is formed when indole-3-acetonitrile (IAN) is catalyzed by the cytochrome P450
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