3-Indoleacrylic acid Chemical Properties

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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

RTECS 

NL3680000

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:3-Indoleacrylic acid
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3-Indoleacrylic acid Usage And Synthesis

Chemical Properties

light yellow to yellow-beige crystalline powder

Uses

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

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.]

3-Indoleacrylic acid(1204-06-4)Related Product Information

• Acrylic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• cis-Octahydro-isoindole
• cis-Octahydroisoindole
• Folic acid
• 6-Benzylaminopurine
• Indometacin
• Indole-3-butyric acid
• Indole-3-acetic acid
• Citric acid
• INDOLE-2-ACETIC ACID
• DL-INDOLE-3-LACTIC ACID
• Indole
• Ascoric Acid
• 3-Indolepropionic acid
• Methyl indole-2-carboxylate
• 1H-indole-3-propylamine
• Indole-3-carbinol