H1771

3-Hydroxy-DL-kynurenine

• Synonym(s): α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acid
• Empirical Formula (Hill Notation): C₁₀H₁₂N₂O₄
• CAS Number: 484-78-6
• Molecular Weight: 224.21
• MDL number: MFCD00047832
• UNSPSC Code: 12352204
• PubChem Substance ID: 24895482
• NACRES: NA.32

Properties

• assay: ≥98% (TLC)
• Quality Level: 200
• form: powder
• solubility: 1 M HCl: 49.00-51.00 mg/mL, clear to very slightly hazy
• storage temp.: 2-8°C
• SMILES string: NC(CC(=O)c1cccc(O)c1N)C(O)=O
• InChI: 1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)
• InChI key: VCKPUUFAIGNJHC-UHFFFAOYSA-N

Description

General description

3-Hydroxy-DL-kynurenine is a tryptophan metabolite with a molecular weight corresponding to 224Da. It is a chromophore or hydrophilic yellow compound present in the lens of the eye. 3-Hydroxy-DL-kynurenine is synthesized from kynurenine by the action of enzyme kynurenine 3-monooxygenase (KMO). It is metabolized to 3-hydroxyanthranilic acid and xanthurenic acid in the presence of enzymes kynureninase and kynurenine aminotransferases, respectively.

Application

3-Hydroxy-DL-kynurenine has been used:

• as a substrate for the recombinant human kynureninase assay
• as a reference standard in tandem mass spectrometry (MS/MS) analysis
• as a control for quantifying serum 3-Hydroxy-DL-kynurenine levels in diabetic retinopathy patients

Biochem/physiol Actions

3-Hydroxy-DL-kynurenine (3-HKYN) has antioxidant functionality and prevents lipid peroxidation in cerebral cortex. It may modulate synaptic neurotransmission. The levels of 3-HKYN is elevated in Huntington′s disease. However, its role in neurodegenerative diseases is still not understood well. Kynurenine metabolism is linked with glutamatergic neurotransmission and the level of 3-HKYN is linked to the pathophysiology of schizophrenia.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves