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286281
Indole-3-acetamide
98%
Synonym(s):
3-Indolylacetamide, NSC 1969
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$77.70
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$107.00
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1 G
$77.70
5 G
$107.00
About This Item
Empirical Formula (Hill Notation):
C10H10N2O
CAS Number:
Molecular Weight:
174.20
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Assay:
98%
Recommended Products
Quality Level
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
General description
Indole-3-acetamide is an auxin precursor[1].
Application
Indole-3-acetamide was used in the synthesis of [5.5.6.6]diazafenestrane skeleton[2] and indole-3-acetic acid[3].
Reactant for the synthesis of:
- PET agent for imaging of protein kinase C
- A potential agent against Prion Disease
- Protein kinase C (PKC) inhibitor bisindolylmaleimide IV
- Glycogen synthase kinase-3ß (GSK-3ß) inhibitors
- Inhibitors of CaMKIId
- 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 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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Chuntao Yin et al.
Molecular plant-microbe interactions : MPMI, 27(3), 227-235 (2013-12-20)
The plant hormone indole-3-acetic acid (IAA) is best known as a regulator of plant growth and development but its production can also affect plant-microbe interactions. Microorganisms, including numerous plant-associated bacteria and several fungi, are also capable of producing IAA. The
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
Rudy Maor et al.
Applied and environmental microbiology, 70(3), 1852-1854 (2004-03-10)
The plant pathogenic fungus Colletotrichum gloeosporioides f. sp. aeschynomene utilizes external tryptophan to produce indole-3-acetic acid (IAA) through the intermediate indole-3-acetamide (IAM). We studied the effects of tryptophan, IAA, and IAM on IAA biosynthesis in fungal axenic cultures and on
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
Atsushi Umehara et al.
Organic letters, 16(9), 2526-2529 (2014-04-24)
Total syntheses of leuconodine B, melodinine E, and leuconoxine were accomplished via a divergent route. The [5.5.6.6]diazafenestrane skeleton was constructed from an indole-3-acetamide derivative via DMDO oxidation to hydroxylindolenine, TMSOTf/2,6-lutidine mediated cyclic aminal formation, and diastereoseletive ring-closing metathesis of a
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