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SML0096

Sigma-Aldrich

Cinnabarinic Acid

≥98% (HPLC)

Synonyme(s) :

2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid, Cinnabaric acid

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About This Item

Formule empirique (notation de Hill):
C14H8N2O6
Numéro CAS:
606-59-7
Poids moléculaire :
300.22
Numéro MDL:
MFCD18379297
Code UNSPSC :
12352106
ID de substance PubChem :
329825154
Nomenclature NACRES :
NA.25

Niveau de qualité

100

Essai

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated

Couleur

red to very dark red

Solubilité

DMSO: ≥4 mg/mL

Température de stockage

2-8°C

Chaîne SMILES 

NC1=C(C(O)=O)C2=Nc3c(OC2=CC1=O)cccc3C(O)=O

InChI

1S/C14H8N2O6/c15-10-6(17)4-8-12(9(10)14(20)21)16-11-5(13(18)19)2-1-3-7(11)22-8/h1-4H,15H2,(H,18,19)(H,20,21)

Clé InChI

FSBKJYLVDRVPTK-UHFFFAOYSA-N

Application

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.

Actions biochimiques/physiologiques

Caspase Inducer; mGlu4R agonist
Caspase Inducer; mGlu4R agonist
Cinnabarinic acid (CA) connects between initiation of the kynurenine pathway and immune tolerance that is used to prevent neuroinflammation.
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.

Caractéristiques et avantages

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
024M4734V
081M4728V

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

S Christen et al.
Biochemistry, 31(34), 8090-8097 (1992-09-01)
Since 3-hydroxyanthranilic acid (3HAA), an oxidation product of tryptophan metabolism, is a powerful radical scavenger [Christen, S., Peterhans, E., & Stocker, R. (1990) Proc. Natl. Acad. Sci. U.S.A. 87, 2506], its reaction with peroxyl radicals was investigated further. Exposure to
U Temp et al.
Applied and environmental microbiology, 65(2), 389-395 (1999-01-30)
When glucose is the carbon source, the white rot fungus Pycnoporus cinnabarinus produces a characteristic red pigment, cinnabarinic acid, which is formed by laccase-catalyzed oxidation of the precursor 3-hydroxyanthranilic acid. When P. cinnabarinus was grown on media containing cellobiose or
Hideaki Iizuka et al.
Biomedical chromatography : BMC, 24(3), 231-234 (2009-07-25)
A fluorimetric detection method for one of the tryptophan metabolites, cinnabarinic acid (CA), which has recently been reported to have the ability to induce apoptosis in thymocytes, was developed using o-tolyl hydrazine (TH) as the derivatization reagent. The carbonyl group
H Ogawa et al.
Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 364(11), 1507-1518 (1983-11-01)
The formation of cinnabarinate in the presence of manganese ions and catalase was investigated spectrophotometrically. The absorption peak of cinnabarinate at 460 nm appeared only in a reaction system containing manganese ions and catalase. If catalase was omitted, a new
H Iwahashi et al.
The Biochemical journal, 251(3), 893-899 (1988-05-01)
Superoxide dismutase (SOD) enhanced the formation of hydroxyl radicals, which were detected by using the e.s.r. spin-trapping technique, in a reaction mixture containing 3-hydroxyanthranilic acid (or p-aminophenol), Fe3+ ions, EDTA and potassium phosphate buffer, pH 7.4. The hydroxyl-radical formation enhanced
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