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SML0096

Sigma-Aldrich

Cinnabarinic Acid

≥98% (HPLC)

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C14H8N2O6
Número de CAS:
606-59-7
Peso molecular:
300.22
Número MDL:
MFCD18379297
Código UNSPSC:
12352106
ID de la sustancia en PubChem:
329825154
NACRES:
NA.25

Nivel de calidad

100

Ensayo

≥98% (HPLC)

Formulario

powder

condiciones de almacenamiento

desiccated

color

red to very dark red

solubilidad

DMSO: ≥4 mg/mL

temp. de almacenamiento

2-8°C

cadena 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)

Clave InChI

FSBKJYLVDRVPTK-UHFFFAOYSA-N

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

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Certificados de análisis (COA)

Lot/Batch Number
0000427122
0000427122
0000380789
0000227630
0000227630

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

H Ogawa et al.
Hoppe-Seyler's Zeitschrift fur physiologische Chemie, 364(8), 1059-1066 (1983-08-01)
Cinnabarinic acid was formed from 3-hydroxyanthranilic acid during incubation with a soluble fraction from Malpighian tubules of the silkworm, Bombyx mori, in the presence of manganese ion. The enzyme having this activity was purified to homogeneity by ammonium sulfate fractionation
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
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
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
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
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