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I2273

Sigma-Aldrich

3-Indoleacrylic acid

BioReagent, ≥98% (HPLC)

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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

product line

BioReagent

assay

≥98% (HPLC)

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
57400I2886I5386
vibrant-m

I2273

3-Indoleacrylic acid

vibrant-m

57400

Indole-3-propionic acid

vibrant-m

I2886

3-Indoleacetic acid

vibrant-m

I5386

Indole-3-butyric acid

assay

≥98% (HPLC)

assay

≥99.0% (T)

assay

≥98%

assay

-

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

mol wt

187.19  g/mol

mol wt

-

mol wt

-

mol wt

-

storage temp.

room temp

storage temp.

-

storage temp.

−20°C

storage temp.

2-8°C

grade

for molecular biology

grade

-

grade

-

grade

-

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.

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

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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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)
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)
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)

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