H1771
3-Hydroxy-DL-kynurenine
Synonym(s):
α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acid
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About This Item
Empirical Formula (Hill Notation):
C10H12N2O4
CAS Number:
Molecular Weight:
224.21
NACRES:
NA.32
PubChem Substance ID:
UNSPSC Code:
12352204
MDL number:
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)
SMILES string
NC(CC(=O)c1cccc(O)c1N)C(O)=O
InChI key
VCKPUUFAIGNJHC-UHFFFAOYSA-N
assay
≥98% (TLC)
form
powder
solubility
1 M HCl: 49.00-51.00 mg/mL, clear to very slightly hazy
storage temp.
2-8°C
Quality Level
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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.
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
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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Sarah S Zaher et al.
Investigative ophthalmology & visual science, 52(5), 2640-2648 (2011-01-08)
IDO (indoleamine 2,3-dioxygenase) modulates the immune response by depletion of the essential amino acid tryptophan, and IDO overexpression has been shown to prolong corneal allograft survival. This study was conducted to examine the effect of kynurenines, the products of tryptophan
Yuri P Tsentalovich et al.
Investigative ophthalmology & visual science, 52(10), 7687-7696 (2011-08-30)
To compare the photochemical properties of UV filter molecules present in the human lens (kynurenine, KN; 3-hydroxykynurenine, 3OHKN; 3-hydroxykynurenine O-β-D-glucoside, 3OHKG; 4-(2-aminophenyl)-4-oxobutanoic acid, AHA; and glutathionyl-kynurenine, GSH-KN) with the use of the following parameters: excited singlet lifetime τ(S), fluorescence quantum
A M Myint et al.
Brain, behavior, and immunity, 25(8), 1576-1581 (2011-05-31)
The association between the pro-inflammatory state of schizophrenia and increased tryptophan degradation into kynurenine has been reported. However, the relationship between metabolites from subdivisions of the kynurenine pathway, kynurenic acid and 3-hydroxykynurenine, remains unknown. The present study tested the relationship
Todd Bradley et al.
Journal of immunology (Baltimore, Md. : 1950), 197(12), 4663-4673 (2016-11-17)
The HIV-1 envelope protein (Env) has evolved to subvert the host immune system, hindering viral control by the host. The tryptophan metabolic enzyme kynureninase (KYNU) is mimicked by a portion of the HIV Env gp41 membrane proximal region (MPER) and
Mass spectrometric identification of urinary biomarkers of pulmonary tuberculosis
Isa F, et al.
EBioMedicine, 31(12), 157-165 (2018)
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