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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
MDL number:
MFCD18379297
UNSPSC Code:
12352106
PubChem Substance ID:
329825154
NACRES:
NA.25

assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

red to very dark red

solubility

DMSO: ≥4 mg/mL

storage temp.

2-8°C

SMILES string

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)

InChI key

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Y Nagamura et al.
Advances in experimental medicine and biology, 467, 419-423 (2000-03-18)
Tryptophan administration aggravates experimental mouse liver injury caused by carbon tetrachloride when 3-hydroxyanthranilic acid concentration elevates in serum. Tryptophan metabolism is changed by macrophages in injured liver. 3-Hydroxyanthranilic acid may be oxidized to cinnabarinic acid by injured mitochondria in the
J A Dykens et al.
Biochemical pharmacology, 36(2), 211-217 (1987-01-15)
The oxidative reactivities of four tryptophan metabolites in the kynurenine pathway were examined as a potential mechanism for their reported neurotoxicities and carcinogenicities. Neither quinolinic acid, a neurotoxin, nor its monocarboxylic analogue, picolinic acid, auto-oxidized over a wide pH range.
C Eggert
Microbiological research, 152(3), 315-318 (1997-11-14)
Concentrated culture fluid of the wood-rotting basidiomycete Pycnoporus cinnabarinus showed biological activity against a variety of bacterial strains. The maximal inhibitory effect was obtained for Gram-positive bacteria of the genus Streptococcus. In general, inhibition was higher for Gram-positive than Gram-negative
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(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
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Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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