H1771
3-Hydroxy-DL-kynurenine
Synonyme(s) :
α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acid
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A propos de cet article
Formule empirique (notation de Hill) :
C10H12N2O4
Numéro CAS:
Poids moléculaire :
224.21
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352204
MDL number:
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≥98% (TLC)
Quality Level
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
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Oivind Midttun et al.
The Journal of nutrition, 141(4), 611-617 (2011-02-12)
It is unclear whether reduced plasma pyridoxal 5'-phosphate (PLP) during inflammation reflects an altered distribution or increased requirement of vitamin B-6 that may impair overall vitamin B-6 status in tissues. In plasma from 3035 patients undergoing coronary angiography for suspected
3-Hydroxykynurenine and 3-hydroxyanthranilic acid enhance the toxicity induced by copper in rat astrocyte culture
Ramirez-Ortega D, et al.
Oxidative Medicine and Cellular Longevity, 2017, 189-204 (2017)
Tomasz Kocki et al.
Journal of neural transmission (Vienna, Austria : 1996), 119(2), 235-243 (2011-06-11)
Altered function of kynurenine pathway has emerged recently as one of the factors contributing to the pathogenesis of depression. Neuroprotective kynurenic acid (KYNA) and neurotoxic 3-hydroxykynurenine (3-HK) are two immediate metabolites of L: -kynurenine. Here, we aimed to assess the