cinnabarinic acid Property

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.

Safety

WGK Germany 

3

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

cinnabarinic acid Chemical Properties,Usage,Production

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 derivative, Cinnabarinic acid is obtained in vitro with aid of laccase by oxidative dimerization of 3-Hydroxyanthranilic acid (a metabolite of the amino acid Trytophan). Cinnabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase.

Uses

Cinnabarinic acid may be used in studies of the functions of components of the kynurenine metabolic pathway. It may be used to study it role as a metabotropic glutamate receptor (mGlu4R-specific) agonist.

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

-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