K3375

Kynurenic acid

Name: Kynurenic acid
Brand: SIGMA

≥98% (HPLC), powder, NMDA receptor antagonist

Synonym(s):

4-Hydroxyquinoline-2-carboxylic acid

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₇NO₃

CAS Number:

492-27-3

Molecular Weight:

189.17

NACRES:

NA.77

PubChem Substance ID:

24277986

UNSPSC Code:

12352106

EC Number:

207-751-5

MDL number:

MFCD00006753

Beilstein/REAXYS Number:

147451

Product Name

Kynurenic acid, ≥98%

InChI key

HCZHHEIFKROPDY-UHFFFAOYSA-N

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)

SMILES string

OC(=O)c1cc(O)c2ccccc2n1

assay

≥98%

form

powder

mp

275 °C (dec.) (lit.)

Quality Level

200

Gene Information

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Bioactive Small Molecules

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.

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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Relevance of Alternative Routes of Kynurenic Acid Production in the Brain

Ramos-Chavez LA, et al.

Oxidative Medicine and Cellular Longevity, 2018 (2018)

Inhibiting Stearoyl-CoA Desaturase Ameliorates alpha-Synuclein Cytotoxicity

Vincent BM, et al.

Cell Reports, 25(10), 2742-2754 (2018)

Kynurenic acid content in selected culinary herbs and spices

Turski MP, et al.

Journal of Chemistry, 2015, 1386-1397 (2015)

Glio-and neuro-protection by prosaposin is mediated by orphan G-protein coupled receptors GPR37L1 and GPR37

Liu B, et al.

Glia, 66(11), 2414-2426 (2018)

Mixed-species RNA-seq for elucidation of non-cell-autonomous control of gene transcription

Qiu J, et al.

Nature Protocols, 13(10), 2176-2176 (2018)

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