N-formylkynurenine

Base Information

• Chemical Name: N-formylkynurenine
• CAS No.: 1022-31-7
• Molecular Formula: C11H12 N2 O4
• Molecular Weight: 236.227
• Hs Code.: 2924299090
• NSC Number: 334199
• UNII: N3FFD7AJC9
• DSSTox Substance ID: DTXSID10862515
• Nikkaji Number: J426.764H
• Wikipedia: N'-Formylkynurenine
• Wikidata: Q71982
• Mol file: 1022-31-7.mol

Synonyms:N'-formylkynurenine;N'-formylkynurenine, (R)-isomer;N'-formylkynurenine, (S)-isomer;N-formylkynurenine

Chemical Property of N-formylkynurenine

Chemical Property:

• Vapor Pressure: 1.58E-13mmHg at 25°C
• Melting Point: 169-170 °C
• Boiling Point: 563.4°Cat760mmHg
• PKA: 2.17±0.23(Predicted)
• Flash Point: 294.5°C
• PSA: 109.49000
• Density: 1.394g/cm³
• LogP: 1.64880
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, So
• XLogP3: -2.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 236.07970687
• Heavy Atom Count: 17
• Complexity: 306

Purity/Quality:

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

N''-Formylkynurenine ^*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)NC=O
• Uses: N''-Formylkynurenine is a photooxidation product of Tryptophan (T947200), and is also used as a photosensitizer of near-ultraviolet radiation by generating singlet oxygen and superoxide.

Technology Process of N-formylkynurenine

There total 16 articles about N-formylkynurenine 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: 72.0%

3a-hydroperoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid (70938-99-7) → 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid (1022-31-7,3978-11-8)

Guidance literature:

With sodium carbonate; acetic acid; for 0.166667h;

DOI:10.1039/c39810000855

Reference yield: 54.0%

L-Tryptophan (73-22-3,27732-43-0,80206-30-0,27813-82-7) → 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid (1022-31-7,3978-11-8)

Guidance literature:

With oxygen; methylene blue; sodium carbonate; acetic acid; at 0 - 5 ℃; for 0.5h; Irradiation;

DOI:10.1039/c39810000855

Reference yield: 42.0%

Trp (54-12-6,27732-43-0,80206-30-0,27813-82-7) → 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid (1022-31-7,3978-11-8) + 3a-hydroxy-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole-2-carboxylic acid (35169-97-2)

Guidance literature:

With 3-(1,4-dihydro-1,4-epidioxy-4-methyl-1-naphthyl)propionic acid; In methanol; water; at 35 ℃;

DOI:10.1021/ja00391a035

upstream raw materials:

Trp

L(-)-tryptophan

3a-hydroperoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid

2-carboxy-3a-hydroperoxy-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole

Refernces

• 1、 Tamagaki, Seizo,Liesner, Cathy E.,Neckers, Douglas C.. "Polymer-Based Sensitizers for Photochemical Reactions. Silica gel as a Support". . p. 1573 - 1576. Retrieved 1980.
• 2、 Basran, Jaswir,Efimov, Igor,Chauhan, Nishma,Thackray, Sarah J.,Krupa, James L.,Eaton, Graham,Griffith, Gerry A.,Mowat, Christopher G.,Handa, Sandeep,Raven, Emma Lloyd. "The mechanism of formation of N -formylkynurenine by heme dioxygenases". . p. 16251 - 16257. Retrieved 2011.
• 3、 Bracchitta, Giuseppina,Catalfo, Alfio,De Guidi, Guido. "UVA photoinduced yeast protein modifications by methylene blue and naproxen". . p. 967 - 973. Retrieved 2013.
• 4、 Lu, Changyuan,Lin, Yu,Yeh, Syun-Ru. "Inhibitory substrate binding site of human indoleamine 2,3-dioxygenase". . p. 12866 - 12867. Retrieved 2009.
• 5、 Biedermann, Frank,Hathazi, Denisa,Nau, Werner M.. "Associative chemosensing by fluorescent macrocycle-dye complexes-a versatile enzyme assay platform beyond indicator displacement". supporting information. p. 4977 - 4980. Retrieved 2015/03/30.