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I2273

Sigma-Aldrich

3-Indoleacrylic acid

≥98% (HPLC), BioReagent

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:
24895972
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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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
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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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