284734
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:
Molecular Weight:
161.16
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
212-231-6
Beilstein/REAXYS Number:
129435
MDL number:
InChI key
KMAKOBLIOCQGJP-UHFFFAOYSA-N
InChI
1S/C9H7NO2/c11-9(12)7-5-10-8-4-2-1-3-6(7)8/h1-5,10H,(H,11,12)
SMILES string
OC(=O)c1c[nH]c2ccccc12
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
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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Analytical characterization of some synthetic cannabinoids, derivatives of indole-3-carboxylic acid.
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
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
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
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
Adelle A Vandersteen et al.
The Journal of organic chemistry, 77(15), 6505-6509 (2012-07-19)
Elucidation of the mechanism for decarboxylation of indolecarboxylic acids over a wide range of solution acidity reveals the importance of protonated carbonic acid (PCA) as a reaction intermediate. In concentrated acid, the initial addition of water to the carboxyl group
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