3-Indoleacrylic acid

Chemical properties

light yellow to yellow-beige crystalline powder

The Uses of 3-Indoleacrylic acid

3-Indoleacrylic acid has been used in the induction of ribokinase expression in E. coli.

What are the applications of Application

3-Indoleacrylic acid is which induces transcription of genes under the control of the trpE promoter

Definition

ChEBI: (E)-3-(indol-3-yl)acrylic acid is an alpha,beta-unsaturated monocarboxylic acid that is acrylic acid in which one of the hydrogens at position 3 is replaced by an indol-3-yl group. It is an alpha,beta-unsaturated monocarboxylic acid and a member of indoles. It is functionally related to an acrylic acid. It is a conjugate acid of an (E)-3-(indol-3-yl)acrylate(1-).

Synthesis Reference(s)

Synthesis, p. 236, 1984 DOI: 10.1055/s-1984-30787

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.

Biochem/physiol Actions

3-Indoleacrylic acid helps to block the mycelial growth of?Neurospora crassa. As a result, the cells accumulate indoleglycerol phosphate, which influences the rate of tryptophan synthetase.

Purification Methods

Recrystallise the acid from AcOH, H2O or EtOAc/cyclohexane. UV in MeOH has at 225, 274 and 325nm. [Shaw et al. J Org Chem 23 1171 1958, constitution: Rappe Acta max Chem Scand 18 818 1964, Moffatt J Chem Soc 1442 1957, Kimming et al. Hoppe Seyler's Z Physiol Chem 371 234 1958, Beilstein 22 V 249.]