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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
Pricing and availability is not currently available.

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.[1]

Application

3-Hydroxy-DL-kynurenine has been used:
  • as a substrate for the recombinant human kynureninase assay[2]
  • as a reference standard in tandem mass spectrometry (MS/MS) analysis[3]
  • as a control for quantifying serum 3-Hydroxy-DL-kynurenine levels in diabetic retinopathy patients[4]

Biochem/physiol Actions

3-Hydroxy-DL-kynurenine (3-HKYN) has antioxidant functionality and prevents lipid peroxidation in cerebral cortex. It may modulate synaptic neurotransmission.[1] The levels of 3-HKYN is elevated in Huntington′s disease. However, its role in neurodegenerative diseases is still not understood well.[5] Kynurenine metabolism is linked with glutamatergic neurotransmission and the level of 3-HKYN is linked to the pathophysiology of schizophrenia.[6]

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000410414
0000410424
0000410413
0000394498
0000395819

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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
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
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
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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