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I5109

Indole-2-carboxylic acid

Name: Indole-2-carboxylic acid
Brand: ALDRICH

98%

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Synonym(s):

2-Carboxyindole, 2-Indolylformic acid, NSC 16598

Empirical Formula (Hill Notation):

C₉H₇NO₂

CAS Number:

1477-50-5

Molecular Weight:

161.16

Beilstein:

124132

EC Number:

216-030-4

MDL number:

MFCD00005611

PubChem Substance ID:

24895981

NACRES:

NA.22

Quality Level

100

Assay

98%

mp

202-206 °C (lit.)

SMILES string

OC(=O)c1cc2ccccc2[nH]1

InChI

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

InChI key

HCUARRIEZVDMPT-UHFFFAOYSA-N

Gene Information

human ... SRD5A1(6715)
rat ... Grin2a(24409)

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Related Categories

Heterocyclic Building Blocks

Application

Reactant for total synthesis of (±)-dibromophakellin and analogs
Reactant for synthesis of the pyrrolizidine alkaloid (±)-trachelanthamidine
Reactant for stereoselective preparation of renieramycin G analogs
Reactant for preparation of spirooxoindolepyrrolidines via reduction of indole-2-carboxylic acid followed by oxidation, condensation, reduction, amidation and Kharasch radical cyclization
Reactant for Pd-catalyzed cyclization
Reactant for preparation of N,N′-(pentane)diylbis[indolecarboxamide] and N,N′-[phenylenebis(methylene)]bis[indolecarboxamide] derivatives

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

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Effect of dimerization on vibrational spectra of eumelanin precursors.

Stephen P Nighswander-Rempel et al.

Photochemistry and photobiology, 84(3), 613-619 (2008-01-23)

We have synthesized a compound ideally suited to the study of structure-function relationships in eumelanin synthesis. N-methyl-5-hydroxy-6-methoxy-indole (MHMI) has key functional groups strategically placed on the indole framework to hinder binding in the 2, 5, 6 and 7 positions. Thus

Substituted indole-2-carboxylates as in vivo potent antagonists acting as the strychnine-insensitive glycine binding site.

R Di Fabio et al.

Journal of medicinal chemistry, 40(6), 841-850 (1997-03-14)

A series of indole-2-carboxylates bearing suitable chains at the C-3 position of the indole nucleus was synthesized and evaluated in terms of in vitro affinity using [3H]glycine binding assay and in vivo potency by inhibition of convulsions induced by N-methyl-D-aspartate

Novel indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives. Structure-activity relationships for high inhibition of human LDL peroxidation.

C Kuehm-Caubere et al.

Journal of medicinal chemistry, 40(8), 1201-1210 (1997-04-11)

Series of indole-2-carboxamide and cycloalkeno[1,2-b]indole derivatives were synthesized and evaluated in order to determine the necessary structural requirements for a high inhibition of human LDL copper-induced peroxidation. Various modulations were systematically performed on the indole and cycloalkeno[1,2-b]indole nuclei as well

Identification of a small set of genes commonly regulated in rice roots in response to beneficial rhizobacteria.

Marine Valette et al.

Physiology and molecular biology of plants : an international journal of functional plant biology, 26(12), 2537-2551 (2021-01-12)

Rhizosphere bacteria, whether phytopathogenic or phytobeneficial, are thought to be perceived by the plant as a threat. Plant Growth-Promoting Rhizobacteria (PGPR), such as many strains of the Azospirillum genus known as the main phytostimulator of cereals, cooperate with host plants

Synthesis and biological activities of novel aryl indole-2-carboxylic acid analogs as PPARgamma partial agonists.

James F Dropinski et al.

Bioorganic & medicinal chemistry letters, 15(22), 5035-5038 (2005-09-13)

A series of novel aryl indole-2-carboxylic acids has been identified as potent selective PPARgamma modulators. Their chemical synthesis and in vitro activities are discussed. Compound 5 was selected for in vivo testing in the db/db mouse model of type 2

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