Skip to Content
Merck
CN

I2273

3-Indoleacrylic acid

BioReagent, ≥98% (HPLC)

Synonym(s):

3-(3-Indolyl)acrylic acid, IAA

Sign In to View Organizational & Contract Pricing.

Select a Size

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
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Product Name

3-Indoleacrylic acid, BioReagent, ≥98% (HPLC)

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

Looking for similar products? Visit Product Comparison Guide

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.

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.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCV7622
MKCQ4803
MKCJ6570
MKCC4059
MKBW9092V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
Identification and functional analyses of differentially expressed metabolites in early stage endometrial carcinoma
Shi K, et al.
Cancer Science, 109(4), 1032-1043 (2018)
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)
View All Related Papers

Related Content

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service