SML0096
Cinnabarinic Acid
≥98% (HPLC), mGlu4R agonist, powder
Synonym(s):
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid, Cinnabaric acid
Sign Into View Organizational & Contract Pricing
Select a Size
About This Item
Empirical Formula (Hill Notation):
C14H8N2O6
CAS Number:
Molecular Weight:
300.22
MDL number:
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.25
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
Related Categories
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
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.
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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 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
Articles
Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service