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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

H1771-250MG:
H1771-25MG:
H1771-250MG-PW:
H1771-100MG-PW:
H1771-BULK:
H1771-100MG:
H1771-VAR:
H1771-25MG-PW:

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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Sigma-Aldrich

10680

Anthranilic acid

Quinaldic acid 98%

Sigma-Aldrich

160660

Quinaldic acid

Anthranilic acid reagent grade, ≥98%

Sigma-Aldrich

A89855

Anthranilic acid

Susanna Campesan et al.
Current biology : CB, 21(11), 961-966 (2011-06-04)
Neuroactive metabolites of the kynurenine pathway (KP) of tryptophan degradation have been implicated in the pathophysiology of neurodegenerative disorders, including Huntington's disease (HD) [1]. A central hallmark of HD is neurodegeneration caused by a polyglutamine expansion in the huntingtin (htt)
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
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
Ruth Condray et al.
The international journal of neuropsychopharmacology, 14(6), 756-767 (2011-01-29)
One branch of the tryptophan catabolic cascade is the kynurenine pathway, which produces neurotoxic [3-hydroxykynurenine (3-OHKY), quinolinic acid] and neuroinhibitory (kynurenic acid) compounds. Kynurenic acid acts as a competitive antagonist at the glycine site of N-methyl-d-asparate receptors at high concentrations
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
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