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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:
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 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

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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Xuejin Zhao et al.
Viruses, 13(8) (2021-08-29)
Influenza A viruses are serious zoonotic pathogens that continuously cause pandemics in several animal hosts, including birds, pigs, and humans. Indole derivatives containing an indole core framework have been extensively studied and developed to prevent and/or treat viral infection. This
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
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