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286281

Indole-3-acetamide

Name: Indole-3-acetamide
Brand: ALDRICH

98%

Synonym(s):

3-Indolylacetamide, NSC 1969

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₀N₂O

CAS Number:

879-37-8

Molecular Weight:

174.20

NACRES:

NA.22

PubChem Substance ID:

24857238

UNSPSC Code:

12352100

EC Number:

212-904-4

MDL number:

MFCD00005641

Assay:

98%

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Properties

Quality Level

100

assay

98%

mp

148-150 °C (lit.)

functional group

amide

SMILES string

NC(=O)Cc1c[nH]c2ccccc12

InChI

1S/C10H10N2O/c11-10(13)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,12H,5H2,(H2,11,13)

InChI key

ZOAMBXDOGPRZLP-UHFFFAOYSA-N

Description

General description

Indole-3-acetamide is an auxin precursor.

Application

Indole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton and indole-3-acetic acid.

Reactant for the synthesis of:

PET agent for imaging of protein kinase C
A potential agent against Prion Disease
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A VEGF inhibitor
JAK3 inhibitors
Inhibitors of NAD+-Dependent Histone Deacetylases
Inhibitors of human adipocyte fatty acid-binding protein
Cyclin-dependent kinase inhibitors

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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Molecular cloning and characterization of an amidase from Arabidopsis thaliana capable of converting indole-3-acetamide into the plant growth hormone, indole-3-acetic acid.

Stephan Pollmann et al.

Phytochemistry, 62(3), 293-300 (2003-03-07)

Acylamidohydrolases from higher plants have not been characterized or cloned so far. AtAMI1 is the first member of this enzyme family from a higher plant and was identified in the genome of Arabidopsis thaliana based on sequence homology with the

Production of indole-3-acetic acid via the indole-3-acetamide pathway in the plant-beneficial bacterium Pseudomonas chlororaphis O6 is inhibited by ZnO nanoparticles but enhanced by CuO nanoparticles.

Christian O Dimkpa et al.

Applied and environmental microbiology, 78(5), 1404-1410 (2012-01-03)

The beneficial bacterium Pseudomonas chlororaphis O6 produces indole-3-acetic acid (IAA), a plant growth regulator. However, the pathway involved in IAA production in this bacterium has not been reported. In this paper we describe the involvement of the indole-3-acetamide (IAM) pathway

Identification and functional characterization of indole-3-acetamide-mediated IAA biosynthesis in plant-associated Fusarium species.

Elena Tsavkelova et al.

Fungal genetics and biology : FG & B, 49(1), 48-57 (2011-11-15)

The plant hormone indole-3-acetic acid (IAA) can be synthesized from tryptophan via the intermediate indole-3-acetamide (IAM). The two genes, IaaM (encoding tryptophan monooxygenase) and IaaH (encoding indole-3-acetamide hydrolase) that constitute the IAM pathway have been described in plant-associated bacteria. We

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Global Trade Item Number

SKU	GTIN
286281-1G	04061826264676
286281-5G	04061832841618