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cinnabarinic acid

Product Name
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
Formula Weight
300.22
MOL File
606-59-7.mol
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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.
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Safety

WGK Germany 
3
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0096
Product name
Cinnabarinic Acid
Purity
≥98% (HPLC)
Packaging
5mg
Price
$138
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0096
Product name
Cinnabarinic Acid
Purity
≥98% (HPLC)
Packaging
25mg
Price
$210.8
Updated
2024/03/01
Cayman Chemical
Product number
11988
Product name
Cinnabarinic Acid
Purity
≥98%
Packaging
10mg
Price
$134
Updated
2024/03/01
Cayman Chemical
Product number
11988
Product name
Cinnabarinic Acid
Purity
≥98%
Packaging
50mg
Price
$597
Updated
2024/03/01
Tocris
Product number
4119
Product name
Cinnabarinic Acid
Purity
≥98%(HPLC)
Packaging
50
Price
$694
Updated
2021/12/16
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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

cinnabarinic acid Preparation Products And Raw materials

Raw materials

Preparation Products

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cinnabarinic acid Suppliers

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606-59-7, cinnabarinic acidRelated Search:


  • 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