13925-12-7

Basic information

• Product Name: myxin
• Synonyms: myxin;1-Hydroxy-6-methoxyphenazine 5,10-dioxide;3C-Antibiotic;6-Methoxy-1-phenazinol 5,10-dioxide;6-Methoxy-1-phenazinol-5,10-dioxide
• CAS NO: 13925-12-7
• Molecular Formula: C₁₃H₁₀N₂O₄
• Molecular Weight: 258.232
• Mol File: 13925-12-7.mol

Chemical Properties

• Melting Point: 120-130°; mp 149° (dec) (Sigg, Toth)
• Boiling Point: 401.48°C (rough estimate)
• Flash Point: 279.7°C
• Appearance: /
• Density: 1.2944 (rough estimate)
• Vapor Pressure: 1.93E-12mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• CAS DataBase Reference: myxin(CAS DataBase Reference)
• NIST Chemistry Reference: myxin(13925-12-7)
• EPA Substance Registry System: myxin(13925-12-7)

Safety Data

• Hazardous Substances Data: 13925-12-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Myxin is used as an antimicrobial agent for its bacteriostatic and antifungal properties, playing a crucial role in the development of new drugs to combat resistant infections. Its antibiotic characteristics also contribute to its potential use in the treatment of various diseases caused by bacterial and fungal pathogens.
Used in Agricultural Industry:
In agriculture, myxin can be employed as a natural pesticide, leveraging its bacteriostatic and antifungal properties to protect crops from harmful microorganisms. This application can help reduce the reliance on synthetic chemicals, promoting a more sustainable and environmentally friendly approach to crop protection.
Used in Cosmetics Industry:
Due to its antimicrobial properties, myxin can be utilized as a preservative in the cosmetics industry. It can help maintain the shelf life of cosmetic products by inhibiting the growth of bacteria and fungi, ensuring the safety and efficacy of these products for consumers.
Used in Food Industry:
In the food industry, myxin can serve as a natural preservative to extend the shelf life of perishable items. Its ability to inhibit the growth of microorganisms can help prevent spoilage and maintain the quality of food products, reducing food waste and ensuring consumer safety.
Used in Research and Development:
Myxin's unique chemical properties and heat evolution characteristics make it an interesting compound for research and development purposes. Scientists can explore its potential applications in various fields, such as materials science, nanotechnology, and energy production, further expanding its utility and impact on society.

InChI:InChI=1/C13H10N2O4/c1-19-11-7-3-5-9-13(11)15(18)8-4-2-6-10(16)12(8)14(9)17/h2-7,18H,1H3

Upstream product

• 68-81-5 iodinin 
• 485-80-3 S-adenosyl-L-methionine 
• 23462-25-1 phenazine-1,6-dicarboxylic acid 
• 69-86-3 1,6-dihydroxyphenazine N₅-monooxide 
• 74-88-4 methyl iodide 
• 112970-44-2 2-bromo-3-methoxyaniline 
• 69-48-7 phenazine-1,6-diol 
• 13925-11-6 1,6-dimethoxyphenazine-N₅,N 10-dioxide 
• 13129-58-3 1-hydroxy-6-methoxyphenazine 
• 90-04-0 2-methoxy-phenylamine 
• 13398-79-3 1,6-dimethoxyphenazine 
• 91-23-6 2-Nitroanisole 

Relevant articles and documents

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.

Total synthesis and antileukemic evaluations of the phenazine 5,10-dioxide natural products iodinin, myxin and their derivatives

A new efficient total synthesis of the phenazine 5,10-dioxide natural products iodinin and myxin and new compounds derived from them was achieved in few steps, a key-step being 1,6-dihydroxyphenazine di-N-oxidation. Analogues prepared from iodinin, including myxin and 2-ethoxy-2-oxoethoxy derivatives, had fully retained cytotoxic effect against human cancer cells (MOLM-13 leukemia) at atmospheric and low oxygen level. Moreover, iodinin was for the first time shown to be hypoxia selective. The structure-activity relationship for leukemia cell death induction revealed that the level of N-oxide functionality was essential for cytotoxicity. It also revealed that only one of the two phenolic functions is required for activity, allowing the other one to be modified without loss of potency.

DNA strand cleavage by the phenazine di- N -oxide natural product myxin under both aerobic and anaerobic conditions

Heterocyclic N-oxides are an interesting class of antitumor agents that selectively kill the hypoxic cells found in solid tumors. The hypoxia-selective activity of the lead compound in this class, tirapazamine, stems from its ability to undergo intracellu

Method for the purification of 6-methoxy-1-phenazinol 5,10-dioxide

A novel improved procedure is described for the preparation of various metal complexes of 6-methoxy-1-phenazinol 5,10-dioxide by the reaction between 6-methoxy-1-phenazinol 5,10-dioxide and a metal salt or hydroxide in an aqueous suspension or a solution in aqueous mineral acid. Preferred metals disclosed as suitable for use in the process are calcium, strontium, magnesium and iron. Utility of the ferric chloride complex and the calcium complex in the purification of 6-methoxy-1-phenazinol 5,10-dioxide is also disclosed.