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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

Quality Level

100

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

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Certificados de análisis (COA)

Lot/Batch Number
0000380789
0000227630
0000380789
024M4734V

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

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
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
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
Journal of chromatography. B, Biomedical sciences and applications, 736(1-2), 237-245 (2000-02-17)
3-Hydroxyanthranilic acid (3-HAA)-derived oxidation products were analyzed using high-performance liquid chromatography with an electrochemical reactor and diode array detection and high-performance liquid chromatography with an electrochemical reactor and UV detection coupled with mass spectrometry. In addition to 3-HAA dimers such
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