Cinnabarinic acid

Base Information

• Chemical Name: Cinnabarinic acid
• CAS No.: 606-59-7
• Molecular Formula: C14H8 N2 O6
• Molecular Weight: 300.227
• UNII: 2XYB6EX2PG
• DSSTox Substance ID: DTXSID30209408
• Nikkaji Number: J21.374H
• Wikidata: Q27106176
• Pharos Ligand ID: T5R3LAU1LLNS
• Metabolomics Workbench ID: 38458
• ChEMBL ID: CHEMBL2322655
• Mol file: 606-59-7.mol

Synonyms:cinnabarinic acid

Chemical Property of Cinnabarinic acid

Chemical Property:

• Vapor Pressure: 2.36E-12mmHg at 25°C
• Melting Point: >300°C
• Boiling Point: 536.8°C at 760 mmHg
• Flash Point: 278.4°C
• PSA: 143.72000
• Density: 1.79
• LogP: 1.85260
• Storage Temp.: Refrigerator
• Solubility.: DMSO: ≥4mg/mL
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 2
• Exact Mass: 300.03823598
• Heavy Atom Count: 22
• Complexity: 675

Purity/Quality:

98%,99%, ^*data from raw suppliers

Cinnabarinic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C2C(=C1)OC3=CC(=O)C(=C(C3=N2)C(=O)O)N)C(=O)O
• Description: Cinnabarinic acid is a phenoxazinone produced by the oxidative dimerization of 3-hydroxyanthranilic acid (3-HAA) as part of the metabolism of tryptophan in the kynurenic pathway. It acts as a partial receptor agonist of the metabotropic glutamate receptor 4 (mGlu4), effective at 100 μM, with no activity at other mGlu receptor subtypes. 3-HAA does not affect mGlu receptors, including mGlu4. Cinnabarinic acid induces apoptosis of T cells at 300-500 μM, a potency some ten times that of 3-HAA.
• Uses: A natural phenoxazinone deriv Cin nabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase. A natural phenoxazinone derivative, Cinnabarinic acid is obtained in vitro with aid of laccase by oxidative dimerization of 3-Hydroxyanthranilic acid (a metabolite of the amino acid Trytophan). Cinnabarinic acid strongly induces apoptosis in thymocytes through the generation of reactive oxygen species and the induction of caspase. 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.

Technology Process of Cinnabarinic acid

There total 11 articles about Cinnabarinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

3-hydroxyanthranilic acid (548-93-6) → cinnabarinic acid (606-59-7)

Guidance literature:

With p-benzoquinone; In ethanol; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm400049z

Reference yield:

3-hydroxyanthranilic acid (548-93-6) → 9-carboxy-2-hydroxy-3H-phenoxazin-3-one (96464-02-7) + cinnabarinic acid (606-59-7) + 6-amino-3-<2'-carboxy-6'-hydroxyphenylamino>-2,5-dioxo-1,3-cyclohexadiene-1-carboxylic acid (112817-49-9) + triphenodioxazine-1,8-dicarboxylic acid (136497-59-1)

Guidance literature:

With potassium phosphate; potassium hexacyanoferrate(III); In water; for 2h; Ambient temperature; pH 7;

Reference yield:

2-nitro-3-benzyloxy-4-methoxybenzoyl chloride (50425-08-6) → cinnabarinic acid (606-59-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / CHCl₃ / Heating

2: 1.) H₂, 2.) p-quinone / 1.) 10percent Pd/C / 1.) methanol, 2.) methanol, 18-20 deg C, 16 h

With hydrogen; p-benzoquinone; palladium on activated charcoal; In chloroform;

upstream raw materials:

3-hydroxyanthranilic acid

3-hydroxy-2-nitrobenzoic acid

N-(3-dimethylaminopropyl)-2-nitro-3-benzyloxy-4-methylbenzamide hydrochloride

N-(3-dimethylaminopropyl)-2-nitro-3-benzyloxy-4-methoxybenzamide hydrochloride

Downstream raw materials:

(4R,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid

(4S,4aS)-2-Amino-4,4a-dihydroxy-3-oxo-10-oxy-4,4a-dihydro-3H-phenoxazine-1,9-dicarboxylic acid

3-hydroxyanthranilic acid

Refernces

• 1、 Carr, Gavin,Tay, Wendy,Bottriell, Helen,Andersen, Sarah K.,Mauk, A. Grant,Andersen, Raymond J.. "Plectosphaeroic acids A, B, and C, Lndoleamine 2,3-dioxygenase inhibitors produced in culture by a marine isolate of the fungus plectosphaerella cucumerina". . p. 2996 - 2999. Retrieved 2009.
• 2、 Achenbach,Blumm. "Investigation of the pigments of Pycnoporus sanguineus. Pycnosanguin and new phenoxazin-3-ones". . p. 3 - 6. Retrieved 1991.
• 3、 Pasceri, Raffaele,Siegel, David,Ross, David,Moody, Christopher J.. "Aminophenoxazinones as inhibitors of indoleamine 2,3-dioxygenase (IDO). synthesis of exfoliazone and chandrananimycin A". . p. 3310 - 3317. Retrieved 2013/06/04.