3-(3-Indolyl)-2-oxopropanoic acid

Synonym(s):3-(3-Indolyl)-2-oxopropanoic acid;3-Indolylpyruvic acid

CAS NO.：392-12-1
Empirical Formula: C11H9NO3
Molecular Weight: 203.19
MDL number: MFCD00005640
EINECS: 206-874-1
SAFETY DATA SHEET (SDS)
Update Date: 2023-06-08 09:03:01

3-(3-Indolyl)-2-oxopropanoic acid Structural

What is 3-(3-Indolyl)-2-oxopropanoic acid?

Description

3-(3-Indolyl)-2-oxopropanoic acid is an important organic compound and an important precursor for the preparation of tryptophan. Tryptophan and D-tryptophan, and DL-tryptophan can also be synthesized by amination hydrogenation. In addition, 3-(3-Indolyl)-2-oxopropanoic acid is an intermediate in the conversion of tryptophan to indoleacetic acid in plants. Indoleacetic acid is an important growth hormone in plants and also plays an important role in regulating plant growth.

Chemical properties

light beige to light brown powder

The Uses of 3-(3-Indolyl)-2-oxopropanoic acid

Indole-3-pyruvic acid can be used:

As a precursor for the synthesis of chromopyrrolic acid by a heme-containing enzyme.
As a reactant in the Biginelli-like scaffold syntheses.

What are the applications of Application

Indole-3-pyruvic acid is an α-Keto analogue of tryptophan

Definition

ChEBI: A 2-oxo monocarboxylic acid that is pyruvic acid substituted by a 1H-indol-3-yl group at position 3. It has been found in Lycopersicon esculentum

Purification Methods

Recrystallise the acid from Me2CO/*C6H6, EtOAc/CHCl3, Me2CO/AcOH (crystals have 1 molecule of AcOH) and dioxane/*C6H6 (with 0.5 molecule of dioxane) [Shaw et al. J Org Chem 23 1171 1958, Kaper & Veldstra Biochim Biophys Acta 30 401 1958]. The ethyl ester has m 133o (from Et2O), and its 2,4-dinitro-phenylhydrazone has m 255o (from Me2CO). [Baker J Chem Soc 461 1946.] The oxime has m 157o(dec, from EtOAc/Et2O) and pK2 0 3.40 [Ahmad & Spenser Canad J Chem 39 1340 1961]. [Beilstein 22 II 250, 22 III/IV 3080, 22/6 V 324.]

Properties of 3-(3-Indolyl)-2-oxopropanoic acid

Melting point:	215 °C (dec.)(lit.)
Boiling point:	341.49°C (rough estimate)
Density	1.2621 (rough estimate)
refractive index	1.4950 (estimate)
storage temp.	-20°C
solubility	DMSO (Slightly), Methanol (Slightly)
form	Solid
pka	2.61±0.54(Predicted)
color	light yellow
BRN	172966
CAS DataBase Reference	392-12-1(CAS DataBase Reference)
NIST Chemistry Reference	Indole-3-pyruvic acid(392-12-1)
EPA Substance Registry System	Indole-3-pyruvic acid (392-12-1)

Safety information for 3-(3-Indolyl)-2-oxopropanoic 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.