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Cinnabarinic acid | Endogenous AhR ligand

CAS:
606-59-7
Catalog Number:
10-2883
Activity:
Endogenous AhR ligand
Chemical Name:
2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
Alternate Names:
Cinnabaric acid
Molecular Weight:
300.22
Molecular Formula:
C14H8N2O6
Solubility:
Soluble in DMSO (up to 30 mg/ml) or in DMF (up to 25 mg/ml).
Physical Properties:
Red solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°C
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 1 month.
Shipping Code:
RT

Cinnabarinic acid (606-59-7) is a novel endogenous tryptophan metabolite which acts as an aryl hydrocarbon receptor (AHR) agonist.1 It drives IL-22 production by stimulating the differentiation of human and mouse T cells producing IL-22.1 Induces apoptosis in thymocytes.2 Activates type 4 metabotropic glutamate receptors.3 Cinnabarinic acid counteracts excitotoxic neuronal cell death induced by NMDA in mixed cultures of cortical cells. Displays neuroprotective activity.3

References/Citations:

1) Lowe et al. (2014), Identification of cinnabarinic acid as a novel endogenous aryl hydrocarbon receptor ligand that drives IL-22 production;  PLoS One, 9(2) e87877
2) Hiramatsu et al. (2008), Cinnabarinic acid generated from 3-hydroxyanthranilic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase;  J. Cell. Biochem., 103 42
3) Fazio et al. (2012), Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors;  Mol. Pharmacol., 81 643

Cinnabarinic acid | Endogenous AhR ligand is also available in the Cellular Metabolism Library.
CAS:
606-59-7
Catalog Number:
10-2883
Activity:
Endogenous AhR ligand
Chemical Name:
2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
Alternate Names:
Cinnabaric acid
Molecular Weight:
300.22
Molecular Formula:
C14H8N2O6
Solubility:
Soluble in DMSO (up to 30 mg/ml) or in DMF (up to 25 mg/ml).
Physical Properties:
Red solid
Purity:
98% by TLC
NMR (Conforms)
Storage Temperature:
-20°C
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 1 month.
Shipping Code:
RT

Safety Data Sheet:

N/A

Product Data Sheet:

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