1022-31-7

Basic information

• Product Name: 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid
• Synonyms: 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid;N'-Formylkynurenine;2-Amino-4-oxo-4-(2-formylaminophenyl)butanoic acid;α-Amino-2-(formylamino)-γ-oxobenzenebutanoic acid;3-[2-(Formylamino)benzoyl]-L-alanine;N-Formyl-L-kynurenine;Benzenebutanoic acid, a-aMino-2-(forMylaMino)-g-oxo-
• CAS NO: 1022-31-7
• Molecular Formula: C₁₁H₁₂N₂O₄
• Molecular Weight: 236.22
• Mol File: 1022-31-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 169-170 °C
• Boiling Point: 563.4°Cat760mmHg
• Flash Point: 294.5°C
• Appearance: /
• Density: 1.394g/cm³
• Vapor Pressure: 1.58E-13mmHg at 25°C
• Refractive Index: 1.631
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated, So
• PKA: 2.17±0.23(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid(1022-31-7)
• EPA Substance Registry System: 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid(1022-31-7)

Safety Data

• Hazardous Substances Data: 1022-31-7(Hazardous Substances Data)

Usage

Description

2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid is a chemical compound derived from the photooxidation of Tryptophan, with the chemical formula C11H12N2O4. It possesses a unique structure that includes an amino group, a formamidophenyl group, and an oxobutanoic acid moiety. 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid is known for its ability to act as a photosensitizer, generating reactive oxygen species upon exposure to near-ultraviolet radiation.

Uses

Used in Photodynamic Therapy:
2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid is used as a photosensitizer in photodynamic therapy for its ability to generate singlet oxygen and superoxide upon exposure to near-ultraviolet radiation. This property makes it a promising candidate for the treatment of various diseases, including cancer and bacterial infections, by inducing localized cell death and reducing the risk of systemic side effects.
Used in Photochemistry Research:
In the field of photochemistry, 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid serves as a valuable research tool for studying the mechanisms of photooxidation and the generation of reactive oxygen species. Its unique structure and reactivity make it an ideal subject for investigating the interactions between light, molecules, and biological systems.
Used in Analytical Chemistry:
2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid can be employed as a chromophore or fluorophore in analytical chemistry for the detection and quantification of various compounds. Its ability to absorb and emit light in the near-ultraviolet region makes it suitable for use in spectroscopic techniques, such as UV-Vis and fluorescence spectroscopy, to monitor chemical reactions and analyze complex samples.
Used in Material Science:
In material science, 2-amino-4-(2-formamidophenyl)-4-oxo-butanoic acid can be incorporated into the design and synthesis of novel materials with unique optical, electronic, and photochemical properties. Its ability to generate reactive oxygen species upon light exposure can be harnessed to create self-healing materials, sensors, and other advanced technologies that respond to environmental stimuli.

InChI:InChI=1/C11H12N2O4/c12-8(11(16)17)5-10(15)7-3-1-2-4-9(7)13-6-14/h1-4,6,8H,5,12H2,(H,13,14)(H,16,17)/t8-/m0/s1

Upstream product

• 54-12-6 Trp 
• 73-22-3 L-Tryptophan 
• 70938-99-7 3a-hydroperoxy-1,2,3,3a,8,8a-hexahydro-pyrrolo[2,3-b]indole-2-carboxylic acid 
• 64-18-6 formic acid 
• 343-65-7 Kynurenine 
• 152071-32-4 methylene blue 
• 153-94-6 D-tryptophan 
• 70938-99-7 2-carboxy-3a-hydroperoxy-1,2,3,3a,8,8a-hexahydropyrrolo<2,3-b>indole 
• 54-12-6 L(-)-tryptophan 

Relevant articles and documents

A new mechanism of the photochemical oxidation of tryptophan sensitised with the uranyl ion

It has been found that tryptophan oxidation sensitised with the uranyl ion occurs as a chain reaction of Trp+ cation radicals with O2.

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Dye-sensitized Photo-oxygenation of Tryptophan to give N'-Formylkynurenine

Exclusive conversion of the tricyclic hydroperoxide (1) into N'-formylkynurenine (2) has been found to occur in Na2CO3-AcOH (pH 7) and the methylene blue-sensitized photo-oxygenation of tryptophan in the same system has given N'-formylkynurenine as the sole product, in contrast with the reaction in water, which gave compound (1).

Formation of fluorophores from the kynurenine pathway metabolite N-formylkynurenine and cyclic amines involves transamidation and carbon-carbon bond formation at the 2-position of the amine

Background Tryptophan catabolism along the kynurenine pathway is associated with a number of pathologies including cataract formation and cancer. Whilst the chemical reactions of kynurenine are well studied, less is known about the reactivity of its precu

Nitrobenzofurazan derivatives of N′-hydroxyamidines as potent inhibitors of indoleamine-2,3-dioxygenase 1

Tryptophan metabolism through the kynurenine pathway is considered as a crucial mechanism in immune tolerance. Indoleamine 2,3-dioxygenase 1 (IDO1) plays a key role in tryptophan catabolism in the immune system and it is also considered as an important therapeutic target for the treatment of cancer and other diseases that are linked with kynurenine pathway. In this study, a series of nitrobenzofurazan derivatives of N′-hydroxybenzimidamides (1) and N′-hydroxy-2-phenylacetimidamides (2) were synthesized and their inhibitory activities against human IDO1 enzyme were tested using in-vitro and cellular enzyme activity assay. The optimization leads to the identification of potent compounds, 1d, 2i and 2k (IC50 = 39-80 nM), which are either competitive or uncompetitive inhibitors of IDO1 enzyme. These compounds also showed IDO1 inhibition potencies in the nanomolar range (IC50 = 50-71 nM) in MDA-MB-231 cells with no/negligible amount of cytotoxicity. The stronger selectivity of the potent compounds for IDO1 enzyme over tryptophan 2,3-dioxygenase (TDO) enzyme (312-1593-fold) also makes them very attractive for further immunotherapeutic applications.