2-azaniumyl-3-(1H-indol-3-yl)propanoate

Base Information

• Chemical Name: 2-azaniumyl-3-(1H-indol-3-yl)propanoate
• CAS No.: 54-12-6
• Molecular Formula: C11H12N2O2
• Molecular Weight: 204.228
• Hs Code.: 29339990
• Mol file: 54-12-6.mol

Synonyms:2-azaniumyl-3-(1H-indol-3-yl)propanoate;D-Tryptophan, 20;(2S)-2-azaniumyl-3-(1H-indol-3-yl)propanoate;L-Tryptophan, 5;tryptophan zwitterion;SCHEMBL23141136;BDBM92685;CHEBI:64554;2-ammonio-3-(1H-indol-3-yl)propanoate

Chemical Property of 2-azaniumyl-3-(1H-indol-3-yl)propanoate

Chemical Property:

• Appearance/Colour: Wite or off-white powder or crystal
• Melting Point: 289-290 °C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 447.908 °C at 760 mmHg
• PKA: 2.30±0.10(Predicted)
• Flash Point: 224.687 °C
• PSA: 79.11000
• Density: 1.363 g/cm³
• LogP: 1.82260
• Storage Temp.: Store at RT.
• Solubility.: methanol: water (7:3): soluble
• Water Solubility.: 10 g/L (20 ºC)
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 204.089877630
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

99% ^*data from raw suppliers

DL-Tryptophan 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 22-36/37/38-37/38-41
• Safety Statements: 24/25-36/37/39-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CC(C(=O)[O-])[NH3+]
• Uses: An amino acid precursor of serotonin and melatonin. DL-Tryptophan is an amino acid precursor of serotonin and melatonin. It is a dietary supplement for use as an antidepressant, anxiolytic, and sleep aid. DL-tryptophan also can be used as feed nutrition enhancer, antioxidants.

Technology Process of 2-azaniumyl-3-(1H-indol-3-yl)propanoate

There total 57 articles about 2-azaniumyl-3-(1H-indol-3-yl)propanoate 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: 85.0%

DL-γ-glutamaldehydic acid dimethyl acetal (70380-01-7) + phenylhydrazine hydrochloride (59-88-1) → Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With sulfuric acid; In water; for 1h; Heating;

DOI:10.1246/bcsj.62.961

Reference yield: 70.0%

rac-3-(1H-indol-3-yl)-2-(benzoylamino)propionic acid methyl ester (104331-05-7) → Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

In potassium hydroxide; hydrolysis;

DOI:10.1016/S0040-4039(00)81629-9

Reference yield:

N-acetyl-DL-tryptophan (1218-34-4,87-32-1) → Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7)

Guidance literature:

With barium dihydroxide; water;

upstream raw materials:

α-(hydroxyimino)-β-(indol-3-yl)propionic acid

5-(3-indolylmethylene)hydantoin

formylamino-indol-3-ylmethyl-malonic acid

acetylamino-indol-3-ylmethyl-malonic acid

Downstream raw materials:

1-(3-Indolyl)-2-acetamido-3-butanon

DL-tryptophan methyl ester

n-formyl-tryptophan

N^α-(4-methanesulfonyl-2-nitro-phenyl)-DL-tryptophan

Refernces

The First Thermodynamic Data on the Complexation of Amino Acids with Cryptand 222 in Methanol at 298.15 K

10.1039/C39900000116

The research investigates the interaction between the macrobicyclic ligand cryptand 222 and various amino acids in methanol. The study aims to provide the first thermodynamic data on the formation of 1:1 complexes between cryptand 222 and amino acids, including glycine, DL-alanine, DL-phenylalanine, DL-serine, DL-proline, and DL-tryptophan, at 298.15 K. Using titration calorimetry and potentiometric titration, the researchers determined the stability constants (log Ks), Gibbs free energy (ΔG°), enthalpy (ΔH°), and entropy (ΔS°) of these complexation reactions. The results indicate that the amino group of the amino acids is the primary active site for interaction with cryptand 222, and the stability of the complexes is influenced by steric factors from substituent groups on the α-carbon of the amino acids. The study concludes that complexation is enthalpically and entropically favored for most amino acids, except glycine. Additionally, computer modeling suggests that the interaction occurs through hydrogen bonds and electrostatic interactions between the amino group and the oxygen atoms of cryptand 222. The findings have implications for understanding the transport of amino acids across cell membranes, enhancing their solubility in organic solvents, and developing methods for their separation.