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cinnabarinic acid

CAS No.
606-59-7
Chemical Name:
cinnabarinic acid
Synonyms
Cinnabaric Acid;cinnabarinic acid;*Halothane Impurity 5 (Halothane EP Impurity E);2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid;3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo-
CBNumber:
CB31312499
Molecular Formula:
C14H8N2O6
Molecular Weight:
300.22
MDL Number:
MFCD18379297
MOL File:
606-59-7.mol
Last updated:2023-06-30 15:45:59

cinnabarinic acid Properties

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.
FDA UNII 2XYB6EX2PG

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302-H315-H319-H335
Precautionary statements  P261-P280-P301+P312-P302+P352-P305+P351+P338
WGK Germany  3

cinnabarinic acid price More Price(16)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich SML0096 Cinnabarinic Acid ≥98% (HPLC) 606-59-7 5mg $138 2024-03-01 Buy
Sigma-Aldrich SML0096 Cinnabarinic Acid ≥98% (HPLC) 606-59-7 25mg $210.8 2024-03-01 Buy
Cayman Chemical 11988 Cinnabarinic Acid ≥98% 606-59-7 10mg $134 2024-03-01 Buy
Cayman Chemical 11988 Cinnabarinic Acid ≥98% 606-59-7 50mg $597 2024-03-01 Buy
Tocris 4119 Cinnabarinic Acid ≥98%(HPLC) 606-59-7 50 $694 2021-12-16 Buy
Product number Packaging Price Buy
SML0096 5mg $138 Buy
SML0096 25mg $210.8 Buy
11988 10mg $134 Buy
11988 50mg $597 Buy
4119 50 $694 Buy

cinnabarinic acid Chemical Properties,Uses,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

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 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

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

cinnabarinic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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cinnabarinic acid 2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid Cinnabaric Acid 3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo- *Halothane Impurity 5 (Halothane EP Impurity E) 606-59-7 Amines Heterocycles Intermediates & Fine Chemicals Pharmaceuticals