SML0096
Cinnabarinic Acid
≥98% (HPLC), mGlu4R agonist, powder
Synonym(s):
2-amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid, Cinnabaric acid
Sign In to View Organizational & Contract Pricing.
Select a Size
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)
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
assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
red to very dark red
solubility
DMSO: ≥4 mg/mL
storage temp.
2-8°C
Quality Level
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
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
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
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
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
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