I2273

Sigma-Aldrich

3-Indoleacrylic acid

BioReagent, ≥98% (HPLC)

Synonym(s):
IAA, 3-(3-Indolyl)acrylic acid
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

Quality Level

grade

for molecular biology

product line

BioReagent

assay

≥98% (HPLC)

form

powder

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

3-Indoleacrylic acid has been used in the induction of ribokinase expression in E. coli.

Packaging

1, 5 g in poly bottle

Biochem/physiol Actions

3-Indoleacrylic acid (IAA) is metabolized from tryptophan and this conversion is carried out by gut microflora. 3-Indoleacrylic acid (IAA) is a chemical used for the induction of gene transcription. The IAA induced expression system requires the gene of interest cloned in plasmids containing the trp promoter. It promotes the barrier functionality of the intestinal epithelial cells. IAA also favors anti-inflammatory response and is regarded as a potential therapeutic to treat inflammatory bowel disease (IBD). It is also implicated in a variety of cellular processes including apoptosis, autophagy, cell proliferation and migration. In tumor cells, IAA is also reported to hinder tryptophan metabolism.

Certificate of Analysis

Certificate of Origin

Indole-3-propionic acid inhibits gut dysbiosis and endotoxin leakage to attenuate steatohepatitis in rats
Zhao ZH, et al.
Experimental & Molecular Medicine, 51(9), 1-14 (2019)
Effective induction of tryptophan promoter under glucose starvation
MIZUTANI S, et al.
J. Chem. Eng. Jpn., 21(6), 658-660 (1988)
Deuterated nucleotides as chemical probes of RNA structure: a detailed protocol for the enzymatic synthesis of a complete set of nucleotides specifically deuterated at ribose carbons
Azad R, et al.
ScienceOpen Research (2015)
High-expression vectors with multiple cloning sites for construction of trpE fusion genes: pATH vectors.
T J Koerner et al.
Methods in enzymology, 194, 477-490 (1991-01-01)
Identification and functional analyses of differentially expressed metabolites in early stage endometrial carcinoma
Shi K, et al.
Cancer Science, 109(4), 1032-1043 (2018)

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