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H1771

Sigma-Aldrich

3-Hydroxy-DL-kynurenine

Sinonimo/i:

α,2-Diamino-3-hydroxy-γ-oxobenzenebutanoic acid

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About This Item

Formula empirica (notazione di Hill):
C10H12N2O4
Numero CAS:
Peso molecolare:
224.21
Numero MDL:
Codice UNSPSC:
12352204
ID PubChem:
NACRES:
NA.32

Saggio

≥98% (TLC)

Livello qualitativo

Forma fisica

powder

Solubilità

1 M HCl: 49.00-51.00 mg/mL, clear to very slightly hazy

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
VCKPUUFAIGNJHC-UHFFFAOYSA-N

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Descrizione generale

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.

Applicazioni

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

Azioni biochim/fisiol

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.

Pittogrammi

Exclamation mark

Avvertenze

Warning

Indicazioni di pericolo

Classi di pericolo

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

dust mask type N95 (US), Eyeshields, Gloves


Certificati d'analisi (COA)

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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)
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
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)

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