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I1625

Sigma-Aldrich

3-Indoleacrylic acid

powder

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Synonym(s):
3-(3-Indolyl)acrylic acid, IAA
Empirical Formula (Hill Notation):
C11H9NO2
CAS Number:
Molecular Weight:
187.19
Beilstein/REAXYS Number:
6317
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.52

grade

for molecular biology

Quality Level

assay

≥98.0% (HPLC)
≥98.0% (TLC)

form

powder

mol wt

187.19  g/mol

storage temp.

room temp

SMILES string

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

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+

InChI key

PLVPPLCLBIEYEA-AATRIKPKSA-N

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1 of 4

This Item
I538657400220027
3-Indoleacrylic acid powder

I1625

3-Indoleacrylic acid

Indole-3-butyric acid BioReagent, suitable for plant cell culture

I5386

Indole-3-butyric acid

Indole-3-propionic acid ≥99.0% (T)

57400

Indole-3-propionic acid

3-Indolepropionic acid ReagentPlus®, 99%

220027

3-Indolepropionic acid

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

storage temp.

room temp

storage temp.

2-8°C

storage temp.

-

storage temp.

-

mol wt

187.19  g/mol

mol wt

-

mol wt

-

mol wt

-

grade

for molecular biology

grade

-

grade

-

grade

-

form

powder

form

-

form

solid

form

powder

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.

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.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Silicate Standard for IC

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
T Mohammad et al.
Photochemistry and photobiology, 59(2), 189-196 (1994-02-01)
Naked, infectious single-stranded (ss) and double-stranded (ds) DNA from phages S13 and G4 were irradiated with 308 nm UV radiation in the absence and presence of several photobiologically active compounds: E- and Z-urocanic acid (E- and Z-UA), their methyl esters
Patricia Casino et al.
Biochemistry, 46(26), 7728-7739 (2007-06-15)
Substrate channeling in the tryptophan synthase bienzyme complex from Salmonella typhimurium is regulated by allosteric interactions triggered by binding of ligand to the alpha-site and covalent reaction at the beta-site. These interactions switch the enzyme between low-activity forms with open
J G Bell et al.
Prostaglandins, leukotrienes, and essential fatty acids, 63(1-2), 21-25 (2000-09-06)
The fatty acid compositions of red blood cell (RBC) phospholipids from a patient with autistic spectrum disorder (ASD) had reduced percentages of highly unsaturated fatty acids (HUFA) compared to control samples. The percentage of HUFA in the RBC from the

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