| Identification | Back Directory | [Name]
cinnabarinic acid | [CAS]
606-59-7 | [Synonyms]
Cinnabaric Acid
cinnabarinic acid
2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo- | [Molecular Formula]
C14H8N2O6 | [MDL Number]
MFCD18379297 | [MOL File]
606-59-7.mol | [Molecular Weight]
300.22 |
| Chemical Properties | Back Directory | [Melting point ]
>300°C | [density ]
1.79 | [storage temp. ]
2-8°C | [solubility ]
DMSO: ≥4mg/mL | [form ]
powder | [color ]
red to very dark red | [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. |
| Hazard Information | Back Directory | [Description]
Cinnabarinic acid is a phenoxazinone produced by the oxidative dimerization of 3-hydroxyanthranilic acid (3-HAA) as part of the metabolism of tryptophan in the kynurenic pathway. It acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4), effective at 100 μM, with no activity at other mGlu receptor subtypes. 3-HAA does not affect mGlu receptors, including mGlu4. Cinnabarinic acid induces apoptosis of T cells at 300-500 μM, a potency some ten times that of 3-HAA. | [Chemical Properties]
Dark Red Solid | [Uses]
A natural phenoxazinone deriv
Cin
nabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase. | [Definition]
ChEBI: Cinnavalininate is a phenoxazine. | [Biochem/physiol Actions]
Cinnabarinic acid is a kynurenine pathway metabolite of tryptophan, produced by the oxidation of 3-Hydroxyanthranilic acid. Cinnabarinic acid leads to loss of mitochondrial respiration and apoptosis, and has also been shown to be an mGlu4R-specific agonist. | [storage]
Store at -20°C | [References]
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 |
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