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H1771 Sigma-Aldrich

3-Hydroxy-DL-kynurenine

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

  • CAS Number 484-78-6

  • Empirical Formula (Hill Notation) C10H12N2O4

  • Molecular Weight 224.21

  •  MDL number MFCD00047832

  •  PubChem Substance ID 24895482

  •  NACRES NA.32

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Properties

Related Categories Amino Acid, Cell Biology, Metabolic Pathways, Metabolites and Cofactors on the Metabolic Pathways Chart, Metabolomics More...
Quality Level   200
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
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

Packaging

25, 100, 250 mg in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1771.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. H1771.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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