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K3375

Sigma-Aldrich

Kynurenic acid

≥98%

Synonym(s):

4-Hydroxyquinoline-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):
C10H7NO3
CAS Number:
Molecular Weight:
189.17
Beilstein/REAXYS Number:
147451
EC Number:
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥98%

form

powder

mp

275 °C (dec.) (lit.)

SMILES string

OC(=O)c1cc(O)c2ccccc2n1

InChI

1S/C10H7NO3/c12-9-5-8(10(13)14)11-7-4-2-1-3-6(7)9/h1-5H,(H,11,12)(H,13,14)

InChI key

HCZHHEIFKROPDY-UHFFFAOYSA-N

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Application

Kynurenic acid has been used as a constituent in dissection saline solution for embryonic cerebral cortical cells and human primary astrocytes. It has also been used as a medium supplement for murine intestinal epithelial cell line, MODE-K and induced pluripotent stem cell (iPSC)-derived neurons cells.

Biochem/physiol Actions

Kynurenic acid (KynA) is a non-selective antagonist of N-methyl-d-aspartate (NMDA), α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid (AMPA) and kainate receptors. It blocks kainic acid neurotoxicity. Kynurenic acid also blocks nicotinic acetylcholine receptors. It is a by-product of tryptophan catabolic pathway. Kynurenic acid is a neuromodulator and controls the levels of glutamate, dopamine, acetylcholine and α-aminobutyric acid (GABA). KynA controls neuroendocrine functions and altered levels of KynA is a potential marker in depression, schizophrenia Alzheimer′s and Huntington′s diseases. Normal levels of KynA in the brain is crucial for the cognitive function.

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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Product No.
Description
Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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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Kynurenic acid is a nutritional cue that enables behavioral plasticity
Lemieux GA, et al.
Cell, 160(1), 119-131 (2015)
Role of kynurenines in the neurotoxic actions of kainic acid
Behan WMH and Stone TW
British Journal of Pharmacology, 129(8), 1764-1770 (2000)
Inhibiting Stearoyl-CoA Desaturase Ameliorates alpha-Synuclein Cytotoxicity
Vincent BM, et al.
Cell Reports, 25(10), 2742-2754 (2018)
Relevance of Alternative Routes of Kynurenic Acid Production in the Brain
Ramos-Chavez LA, et al.
Oxidative Medicine and Cellular Longevity, 2018 (2018)
Kynurenine pathway inhibition as a therapeutic strategy for neuroprotection
Stone TW, et al.
FEBS Journal, 279(8), 1386-1397 (2012)

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