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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
0000427122
0000427122
0000380789
0000227630
0000227630

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

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
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.
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
C Eggert et al.
FEBS letters, 376(3), 202-206 (1995-12-04)
The phenoxazinone chromophore occurs in a variety of biological systems, including numerous pigments and certain antibiotics. It also appears to form as part of a mechanism to protect mammalian tissue from oxidative damage. During cultivation of the basidiomycete, Pycnoporus cinnabarinus
S Christen et al.
Analytical biochemistry, 200(2), 273-279 (1992-02-01)
A convenient and rapid method for the simultaneous determination by HPLC of 3-hydroxyanthranilic acid and the dimer derived by its oxidation, cinnabarinic acid, is described. Buffers or biological samples containing these two Trp metabolites were acidified to pH 2.0 and
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Bioactive Molecules for Apoptosis

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Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

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