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.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Effective induction of tryptophan promoter under glucose starvation
MIZUTANI S, et al.
J. Chem. Eng. Jpn., 21(6), 658-660 (1988)
Identification and functional analyses of differentially expressed metabolites in early stage endometrial carcinoma
Shi K, et al.
Cancer Science, 109(4), 1032-1043 (2018)
Indoleacrylic acid produced by commensal peptostreptococcus species suppresses inflammation
Wlodarska M, et al.
Cell host & microbe, 22(1), 25-37 (2017)
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)
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)

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