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SML0096

Sigma-Aldrich

Cinnabarinic Acid

≥98% (HPLC)

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:
606-59-7
Molecular Weight:
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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tryptamine ≥97%

Sigma-Aldrich

193747

Tryptamine

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 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
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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