69-48-7

Basic information

• Product Name: 1,6-PHENAZINEDIOL
• Synonyms: 1,6-PHENAZINEDIOL;1,6-Dihydroxyphenazine;Crystalloiodinine B;Phenazine-1,6-diol;1,5-dihydroxyphenazine
• CAS NO: 69-48-7
• Molecular Formula: C₁₂H₈N₂O₂
• Molecular Weight: 212.20412
• Mol File: 69-48-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 278-279℃
• Boiling Point: 477.9°Cat760mmHg
• Flash Point: 242.8°C
• Appearance: /
• Density: 1.47g/cm³
• Vapor Pressure: 9.29E-10mmHg at 25°C
• Refractive Index: 1.737
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1,6-PHENAZINEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-PHENAZINEDIOL(69-48-7)
• EPA Substance Registry System: 1,6-PHENAZINEDIOL(69-48-7)

Safety Data

• Hazardous Substances Data: 69-48-7(Hazardous Substances Data)

Usage

General Description

1,6-phenazinediol, also known as neutral red, is an organic compound with the formula C12H9N3O. It is a red to dark brown crystalline powder that is commonly used as a biological stain, especially for staining cytoplasmic granules and nuclei in cell culture. In addition to its use as a biological stain, 1,6-phenazinediol has also been investigated for its potential anti-cancer and antimicrobial properties. It has been found to inhibit the growth of certain cancer cell lines and exhibit antibacterial and antifungal activity. However, it is also known to be toxic and mutagenic, and caution should be exercised when handling and using this chemical.

InChI:InChI=1/C12H8N2O2/c15-9-5-1-3-7-11(9)14-8-4-2-6-10(16)12(8)13-7/h1-6,13,16H

Upstream product

• 16582-03-9 1,6-diaminophenazine 
• 91-23-6 2-Nitroanisole 
• 934-00-9 3-methocycatechol 
• 23462-25-1 phenazine-1,6-dicarboxylic acid 
• 62842-52-8 6-(hydroxymethyl)phenazine-1-carboxylic acid 
• 617-12-9 chorismic acid 
• 29453-77-8 6-hydroxyphenazine-1-carboxylic acid 
• 112970-44-2 2-bromo-3-methoxyaniline 
• 94-70-2 ortho-phenitidine 
• 90-04-0 2-methoxy-phenylamine 
• 408509-15-9 (2-methoxy-6-nitro-phenyl)-(3-methoxy-2-nitro-phenyl)-amine 
• 36848-41-6 1,6-dinitrophenazine 
• 16554-45-3 2-methoxy-6-nitroaniline 
• 500298-30-6 2-bromo-6-methoxynitrobenzene 

Downstream Products

• 68-81-5 iodinin 
• 1478263-83-0 (E)-6-((3,7-dimethylocta-2,6-dien-1-yl)oxy)-1-hydroxyphenazine 
• 13925-12-7 1-hydroxy-6-methoxy-phenazine-N₅,N₁₀-dioxide 
• 69-86-3 1,6-dihydroxyphenazine N₅-monooxide 
• 13129-58-3 1-hydroxy-6-methoxyphenazine 
• 13925-10-5 1,6-dimethoxy-phenazinol-5-oxide 

Relevant articles and documents

Baraphenazines A-G, Divergent Fused Phenazine-Based Metabolites from a Himalayan Streptomyces

The structures and bioactivities of three unprecedented fused 5-hydroxyquinoxaline/alpha-keto acid amino acid metabolites (baraphenazines A-C, 1-3), two unique diastaphenazine-type metabolites (baraphenazines D and E, 4 and 5) and two new phenazinolin-type (baraphenazines F and G, 6 and 7) metabolites from the Himalayan isolate Streptomyces sp. PU-10A are reported. This study highlights the first reported bacterial strain capable of producing diastaphenazine-type, phenazinolin-type, and izumiphenazine A-type metabolites and presents a unique opportunity for the future biosynthetic interrogation of late-stage phenazine-based metabolite maturation.

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Functional and Structural Analysis of Phenazine O -Methyltransferase LaPhzM from Lysobacter antibioticus OH13 and One-Pot Enzymatic Synthesis of the Antibiotic Myxin

Myxin is a well-known antibiotic that had been used for decades. It belongs to the phenazine natural products that exhibit various biological activities, which are often dictated by the decorating groups on the heteroaromatic three-ring system. The three rings of myxin carry a number of decorations, including an unusual aromatic N5,N10-dioxide. We previously showed that phenazine 1,6-dicarboxylic acid (PDC) is the direct precursor of myxin, and two redox enzymes (LaPhzS and LaPhzNO1) catalyze the decarboxylative hydroxylation and aromatic N-oxidations of PDC to produce iodinin (1.6-dihydroxy-N5,N10-dioxide phenazine). In this work, we identified the LaPhzM gene from Lysobacter antibioticus OH13 and demonstrated that LaPhzM encodes a SAM-dependent O-methyltransferase converting iodinin to myxin. The results further showed that LaPhzM is responsible for both monomethoxy and dimethoxy formation in all phenazine compounds isolated from strain OH13. LaPhzM exhibits relaxed substrate selectivity, catalyzing O-methylation of phenazines with non-, mono-, or di-N-oxide. In addition, we demonstrated a one-pot biosynthesis of myxin by in vitro reconstitution of the three phenazine-ring decorating enzymes. Finally, we determined the X-ray crystal structure of LaPhzM with a bound cofactor at 1.4 ? resolution. The structure provided molecular insights into the activity and selectivity of the first characterized phenazine O-methyltransferase. These results will facilitate future exploitation of the thousands of phenazines as new antibiotics through metabolic engineering and chemoenzymatic syntheses.

Heterocyclic Aromatic N-Oxidation in the Biosynthesis of Phenazine Antibiotics from Lysobacter antibioticus

Heterocyclic aromatic N-oxides often have potent biological activities, but the mechanism for aromatic N-oxidation is unclear. Six phenazine antibiotics were isolated from Lysobacter antibioticus OH13. A 10 gene cluster was identified for phenazine biosynthesis. Mutation of LaPhzNO1 abolished all N-oxides, while non-oxides markedly increased. LaPhzNO1 is homologous to Baeyer-Villiger flavoproteins but was shown to catazlye phenazine N-oxidation. LaPhzNO1 and LaPhzS together converted phenazine 1,6-dicarboxylic acid to 1,6-dihydroxyphenazine N5,N10-dioxide. LaPhzNO1 also catalyzed N-oxidation of 8-hydroxyquinoline.