Synthesis
The indolemethylene hydantoin and NaOH solution are mixed and reacted until the solution is transparent, the pH is adjusted to 8.0~9.0. Then the mixtrue was extracted with ether and acetone respectively, and treated with glacial acetic acid, filtered, washed, and dried to give 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
Uses
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.
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.]
