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Merck
CN

I2273

3-Indoleacrylic acid

BioReagent, ≥98% (HPLC)

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
UNSPSC Code:
12352106
NACRES:
NA.52
PubChem Substance ID:
24895972
EC Number:
214-872-7
Beilstein/REAXYS Number:
6317
MDL number:
MFCD00005633

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InChI key

PLVPPLCLBIEYEA-AATRIKPKSA-N

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+

SMILES string

OC(=O)\C=C\c1c[nH]c2ccccc12

grade

Molecular Biology

product line

BioReagent

assay

≥98% (HPLC)

form

powder

mol wt

187.19  g/mol

storage temp.

room temp

Quality Level

100

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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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCV7622
MKCQ4803
MKCJ6570
MKCC4059
MKBW9092V

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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)
Effective induction of tryptophan promoter under glucose starvation
MIZUTANI S, et al.
J. Chem. Eng. Jpn., 21(6), 658-660 (1988)
Indoleacrylic acid produced by commensal peptostreptococcus species suppresses inflammation
Wlodarska M, et al.
Cell host & microbe, 22(1), 25-37 (2017)
Qiting Zhang et al.
International journal of molecular sciences, 22(11) (2021-06-03)
Epigenetic therapy using histone deacetylase (HDAC) inhibitors has become an attractive project in new drug development. However, DNA methylation and histone acetylation are important epigenetic ways to regulate the occurrence and development of leukemia. Given previous studies, N-(2-aminophenyl)benzamide acridine (8a)
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