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Merck
CN

I1625

3-Indoleacrylic acid

powder

Synonym(s):

3-(3-Indolyl)acrylic acid, IAA

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About This Item

Empirical Formula (Hill Notation):
C11H9NO2
CAS Number:
1204-06-4
Molecular Weight:
187.19
UNSPSC Code:
12352106
NACRES:
NA.52
PubChem Substance ID:
24895938
EC Number:
214-872-7
Beilstein/REAXYS Number:
6317
MDL number:
MFCD00005633
Assay:
≥98.0% (HPLC)
≥98.0% (TLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

3-Indoleacrylic acid, powder

InChI key

PLVPPLCLBIEYEA-AATRIKPKSA-N

InChI

1S/C11H9NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-7,12H,(H,13,14)/b6-5+

SMILES string

OC(=O)\C=C\c1c[nH]c2ccccc12

grade

Molecular Biology

assay

≥98.0% (HPLC)
≥98.0% (TLC)

form

powder

mol wt

187.19  g/mol

storage temp.

room temp

Quality Level

100

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Application

Suitable for induction of gene transcription in systems controlled by the trpE promoter.

Biochem/physiol Actions

3-Indoleacrylic acid helps to block the mycelial growth of Neurospora crassa. As a result, the cells accumulate indoleglycerol phosphate, which influences the rate of tryptophan synthetase.

General description

3-Indoleacrylic acid (IAA) is a chemical used for the induction of gene transcription. This expression system requires that the gene of interest is cloned in plasmids containing the trpE promoter.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ6809
MKCX4360
MKCV7877
MKCX0617
MKCV5548

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Inhibition of tryptophan synthetase by indoleacrylic acid
Matchett W H
Journal of Bacteriology, 110(1), 146-154 (1972)
D N Wilson et al.
RNA (New York, N.Y.), 6(12), 1704-1713 (2001-01-06)
Replacing a cassette of 31 residues from Escherichia coli release factor 1 with the equivalent residues in release factor 2 gave a protein active in codon-specific binding to the ribosome but inactive in peptidyl-tRNA hydrolysis. Such a phenotype is also
Indeok Hwang et al.
Plant molecular biology, 73(6), 629-641 (2010-05-18)
Shoot branching and growth are controlled by phytohormones such as auxin and other components in Arabidopsis. We identified a mutant (igi1) showing decreased height and bunchy branching patterns. The phenotypes reverted to the wild type in response to RNA interference
J K Johnson et al.
Biochemistry, 33(15), 4738-4744 (1994-04-19)
In a previous paper, we demonstrated that the medium-chain fatty acyl-CoA dehydrogenase-catalyzed (MCAD-catalyzed) reductive half-reaction of indolepropionyl-CoA proceeds via formation of a chromophoric intermediary species "X" (absorption maximum = 400 nm) and proposed that the decay of this species might
E Marklová
Amino acids, 17(4), 401-413 (2000-03-09)
In addition to the main catabolic routes of tryptophan (Trp), there exist minor and less thoroughly investigated pathways; one of these leads to indolylacrylic acid (IAcrA). IAcrA is a plant growth hormone, whereas its biological role in animals is still
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