3-Indoleacrylic acid

Synonym(s):3-(3-Indolyl)acrylic acid;IAA

CAS NO.：1204-06-4
Empirical Formula: C11H9NO2
Molecular Weight: 187.19
MDL number: MFCD00005633
EINECS: 214-872-7
SAFETY DATA SHEET (SDS)
Update Date: 2023-05-04 17:34:32

What is 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.]

Properties of 3-Indoleacrylic acid

Melting point:	185 °C (dec.)(lit.)
Boiling point:	321.94°C (rough estimate)
Density	1.1963 (rough estimate)
refractive index	1.4900 (estimate)
storage temp.	room temp
form	powder
pka	4.59±0.10(Predicted)
color	white to light yellow
Water Solubility	freely soluble
BRN	6317
CAS DataBase Reference	1204-06-4(CAS DataBase Reference)
EPA Substance Registry System	2-Propenoic acid, 3-(1H-indol-3-yl)- (1204-06-4)

Safety information for 3-Indoleacrylic acid

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.