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H1771

Sigma-Aldrich

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:
484-78-6
Molecular Weight:
224.21
MDL number:
MFCD00047832
UNSPSC Code:
12352204
PubChem Substance ID:
24895482
NACRES:
NA.32

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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