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I1625

Sigma-Aldrich

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
Beilstein:
6317
EC Number:
214-872-7
MDL number:
MFCD00005633
UNSPSC Code:
12352106
PubChem Substance ID:
24895938
NACRES:
NA.52

grade

for molecular biology

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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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.

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

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

Certificates of Analysis (COA)

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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
Protein-ligand interactions: exchange processes and determination of ligand conformation and protein-ligand contacts.
L Y Lian et al.
Methods in enzymology, 239, 657-700 (1994-01-01)
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
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
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