Indole-3-pyruvic acid

Base Information

• Chemical Name: Indole-3-pyruvic acid
• CAS No.: 392-12-1
• Molecular Formula: C11H9NO3
• Molecular Weight: 203.197
• Hs Code.: 2918300090
• European Community (EC) Number: 206-874-1
• NSC Number: 88874
• UNII: 4QM0LT13A8
• DSSTox Substance ID: DTXSID3042053
• Nikkaji Number: J39.033J
• Wikidata: Q23905803
• Metabolomics Workbench ID: 49804
• ChEMBL ID: CHEMBL485012
• Mol file: 392-12-1.mol

Synonyms:indol-3-yl pyruvic acid;indole-3-pyruvic acid

Chemical Property of Indole-3-pyruvic acid

Chemical Property:

• Appearance/Colour: light beige to light brown powder
• Vapor Pressure: 1.04E-08mmHg at 25°C
• Melting Point: 215 °C (dec.)(lit.)
• Refractive Index: 1.4950 (estimate)
• Boiling Point: 445.2 °C at 760 mmHg
• PKA: 2.61±0.54(Predicted)
• Flash Point: 223 °C
• PSA: 70.16000
• Density: 1.421 g/cm³
• LogP: 1.36410
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 203.058243149
• Heavy Atom Count: 15
• Complexity: 277

Purity/Quality:

98%,99%, ^*data from raw suppliers

Indole-3-pyruvic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(=O)C(=O)O
• 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.
• 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.

Technology Process of Indole-3-pyruvic acid

There total 24 articles about Indole-3-pyruvic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Indole-3-pyruvic acid (392-12-1) + (S)-2-hydroxy-3-(1H-indol-3-yl)-propionic acid (7417-65-4,1821-52-9)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

Reference yield: 83.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Indole-3-pyruvic acid (392-12-1) + (R)-2-hydroxy-3-(1H-indol-3-yl)propanoic acid (101312-07-6,1821-52-9)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

Reference yield: 72.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → Indole-3-pyruvic acid (392-12-1) + indole-3-lactic acid (832-97-3,1821-52-9)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

upstream raw materials:

indol-3-yl-pyruvic acid ethyl ester

4-(1'H-indol-3'-ylmethylene)-2-methyl-5(4H)oxazolone

5-(3-indolylmethylene)hydantoin

2-imino-3-(indol-3-yl)propanoic acid

Downstream raw materials:

Ethyl α-(benzyloxamino)-β-(indol-3-yl)propanoate

α-(benzyloximino)-β-(indol-3-yl)-N-methylpropanamide

1-<(E)-benzyloximino>-2-(N-methylindol-3-yl)N-methylpropanamide

ethyl α-(benzyloximino)-β-(N-methylindol-3-yl) propanoate

Refernces

• 1、 Furuya, Yuji,Sawada, Hidemi,Hirahara, Toshikatsu,Ito, Kazue,Ohshiro, Takashi,Izumi, Yoshikazu. "A Novel Enzyme, L-Tryptophan Oxidase, from a Basidiomycete, Coprinus sp. SF-1: Purification and Characterization". . p. 1486 - 1493. Retrieved 2000.
• 2、 Yuan, Yuxiang,Song, Wei,Liu, Jia,Chen, Xiulai,Luo, Qiuling,Liu, Liming. "Production of α-Ketoisocaproate and α-Keto-β-Methylvalerate by Engineered L-Amino Acid Deaminase". . p. 2464 - 2472. Retrieved 2019/05/10.
• 3、 Pishchugin,Tuleberdiev. "Kinetics and mechanism of the condensation of pyridoxal hydrochloride with L-tryptophan and D-tryptophan, and the chemical transformation of their products". . p. 1851 - 1854. Retrieved 2017/09/27.