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H1771

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
NACRES:
NA.32
PubChem Substance ID:
24895482
UNSPSC Code:
12352204
MDL number:
MFCD00047832

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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)

SMILES string

NC(CC(=O)c1cccc(O)c1N)C(O)=O

InChI key

VCKPUUFAIGNJHC-UHFFFAOYSA-N

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

Quality Level

200

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This Item
MABN26537804761250
3-Hydroxy-DL-kynurenine

Sigma-Aldrich

H1771

3-Hydroxy-DL-kynurenine

Anti-3-Hydroxykynurenine Antibody, clone 2c4-B6-C2

Sigma-Aldrich

MABN2653

Anti-3-Hydroxykynurenine Antibody, clone 2c4-B6-C2

3-Hydroxy-DL-kynurenine analytical standard

Supelco

78047

3-Hydroxy-DL-kynurenine

DL-Kynurenine ≥95.0% (NT)

Sigma-Aldrich

61250

DL-Kynurenine

assay

≥98% (TLC)

assay

-

assay

≥90.0% (HPLC)

assay

≥95.0% (NT)

solubility

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

solubility

-

solubility

-

solubility

-

Quality Level

200

Quality Level

200

Quality Level

-

Quality Level

100

form

powder

form

-

form

powder

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

-

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000492352
0000492352
0000488000
0000488000
0000445535

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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
HIV-1 envelope mimicry of host enzyme kynureninase does not disrupt tryptophan metabolism
Bradley T, et al.
Journal of immunology (Baltimore, Md. : 1950), 197(12), 4663-4673 (2016)
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
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)
Mass spectrometric identification of urinary biomarkers of pulmonary tuberculosis
Isa F, et al.
EBioMedicine, 31(12), 157-165 (2018)
View All Related Papers

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/418/501/product-dating-information-06-25-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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