SML0096
Cinnabarinic Acid
≥98% (HPLC), mGlu4R agonist, powder
Synonym(s):
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid, Cinnabaric acid
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About This Item
Empirical Formula (Hill Notation):
C14H8N2O6
CAS Number:
Molecular Weight:
300.22
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
MDL number:
Product Name
Cinnabarinic Acid, ≥98% (HPLC)
Quality Level
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
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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 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.
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 (CA) connects between initiation of the kynurenine pathway and immune tolerance that is used to prevent neuroinflammation.
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
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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.
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
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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