Kynurenine

Base Information

• Chemical Name: Kynurenine
• CAS No.: 343-65-7
• Deprecated CAS: 3039-10-9
• Molecular Formula: C10H12N2O3
• Molecular Weight: 208.217
• Hs Code.: 2922509090
• European Community (EC) Number: 206-445-9
• UNII: 298M20B2AU
• DSSTox Substance ID: DTXSID90861884
• Nikkaji Number: J5.688J
• Wikipedia: Kynurenine
• Wikidata: Q32908783
• NCI Thesaurus Code: C129555
• Metabolomics Workbench ID: 123397
• ChEMBL ID: CHEMBL1377927
• Mol file: 343-65-7.mol

Synonyms:Kynurenine

Chemical Property of Kynurenine

Chemical Property:

• Vapor Pressure: 1.66E-09mmHg at 25°C
• Melting Point: ~235 °C (dec.)
• Refractive Index: 1.625
• Boiling Point: 466.556 °C at 760 mmHg
• PKA: 2.21±0.23(Predicted)
• Flash Point: 235.965 °C
• PSA: 106.41000
• Density: 1.344 g/cm³
• LogP: 1.53500
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Acid (Slightly), Water (Slightly, Heated, Sonicated)
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 208.08479225
• Heavy Atom Count: 15
• Complexity: 255

Purity/Quality:

98%, ^*data from raw suppliers

rac Kynurenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
• Uses: A tryptophan metabolite, is a precursor of kynurenic acid, which is an antagonist of N-methyl-aspartate receptor. An amino acid produced in the body from tryptophan vasodilator, immunomodulator A tryptophan metabolite, is a precursor of kynurenic acid, which is an antagonist of N-methyl-aspartate receptor. An amino acid produced in the body from tryptophan.

Technology Process of Kynurenine

There total 17 articles about Kynurenine 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: 61.0%

oxindolylalanine (32999-55-6) → L-kynurenine (343-65-7,2922-83-0,3039-10-9,13441-51-5)

Guidance literature:

at 50 - 60 ℃; for 0.333333h;

DOI:10.1016/S0040-4039(00)98249-2

Reference yield:

methylene blue (152071-32-4,105504-42-5,121067-62-7,12262-49-6,167498-52-4,6476-03-5,97130-83-1) + Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → tryptamine (61-54-1) + quinolin-4-ol (611-36-9) + 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid (1022-31-7,3978-11-8) + Kynurenine (343-65-7)

Guidance literature:

With Saccharomyces cerevisiae wild type strain V₃₂₈; for 0.333333h; UV-irradiation;

DOI:10.1039/c3pp25359g

Reference yield:

Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → 2,4,6-triamino-s-triazine (108-78-1,25778-04-5,94977-27-2) + serin (302-84-1,83245-15-2) + 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid (1022-31-7,3978-11-8) + Kynurenine (343-65-7) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + aspartic Acid (617-45-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3)

Guidance literature:

With oxygen; ozone; In water; for 1h; Product distribution; Mechanism;

upstream raw materials:

(o-nitrobenzoyl)alanine

2-hydroxyimino-4-(2-nitro-phenyl)-4-oxo-butyric acid ethyl ester

Trp

L(-)-tryptophan

Downstream raw materials:

kynuramine

ammonia

2-aminoacetophenone

methylammonium carbonate

Refernces

• 1、 Bracchitta, Giuseppina,Catalfo, Alfio,De Guidi, Guido. "UVA photoinduced yeast protein modifications by methylene blue and naproxen". . p. 967 - 973. Retrieved 2013/09/12.
• 2、 Bhatt, Rachana,Shrimali, P. S.,Ameta, S. C.,Chowdhry, H. C.. "PHOTOOXIDATION OF L(-)-TRYPTOPHAN BY URANYL IONS". . p. 388 - 390. Retrieved 2007/10/02.