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K3375

Sigma-Aldrich

Kynurenic acid

≥98%

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Synonym(s):
4-Hydroxyquinoline-2-carboxylic acid
Empirical Formula (Hill Notation):
C10H7NO3
CAS Number:
492-27-3
Molecular Weight:
189.17
Beilstein:
147451
EC Number:
207-751-5
MDL number:
MFCD00006753
UNSPSC Code:
12352106
PubChem Substance ID:
24277986
NACRES:
NA.77

Quality Level

200

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

Gene Information

human ... CHRNA1(1134) , CHRNA10(57053) , CHRNA2(1135) , CHRNA3(1136) , CHRNA4(1137) , CHRNA5(1138) , CHRNA6(8973) , CHRNA7(1139) , CHRNA9(55584) , CHRNB1(1140) , CHRNB2(1141) , CHRNB3(1142) , CHRNB4(1143) , GRIA3(2892) , GRIA4(2893) , GRIK1(2897) , GRIK2(2898) , GRIK3(2899) , GRIK4(2900) , GRIK5(2901) , GUCA2A(2980) , GUCA2B(2981) , NGFR(4804) , SLC23A2(9962)
rat ... Gria1(50592) , Grik1(29559) , Grin2a(24409)

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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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Flash Point(F)

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Flash Point(C)

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Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)
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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