Monensin, monosodium salt

Base Information

• Chemical Name: Monensin, monosodium salt
• CAS No.: 22373-78-0
• Molecular Formula: C36H61NaO11
• Molecular Weight: 692.864
• Hs Code.: 29419090
• European Community (EC) Number: 244-941-7
• DSSTox Substance ID: DTXSID90944782
• NCI Thesaurus Code: C82249
• Nikkaji Number: J25.129A
• Mol file: 22373-78-0.mol

Synonyms:Coban;Monensin;Monensin A Sodium Complex;Monensin Monosodium Salt;Monensin Sodium;Monensin-A-Sodium Complex;Rumensin

Chemical Property of Monensin, monosodium salt

Chemical Property:

• Appearance/Colour: light cream amorphous powder
• Vapor Pressure: 4.13E-27mmHg at 25°C
• Melting Point: 267-269 °C
• Boiling Point: 766.3 °C at 760 mmHg
• Flash Point: 229.2 °C
• PSA: 165.43000
• LogP: 2.87390
• Storage Temp.: 2-8°C
• Solubility.: Soluble in methanol at 50mg/ml
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 692.41115704
• Heavy Atom Count: 48
• Complexity: 1110

Purity/Quality:

20% 40% 90% ^*data from raw suppliers

Monensin sodium salt ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, T+
• Hazard Codes: T,T+
• Statements: 25-26/27/28
• Safety Statements: 36/37/39-45-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1(CCC(O1)C2(CCC3(O2)CC(C(C(O3)C(C)C(C(C)C(=O)[O-])OC)C)O)C)C4C(CC(O4)C5C(CC(C(O5)(CO)O)C)C)C.[Na+]
• Description: Monensin is a naturally occuring ionophorous antibiotic that preferentially forms complexes with monovalent cations to enable transport across lipid membranes. Through its ability to affect pH and the sodium-potassium balance of a cell, monensin can induce cell death in Gram-positive bacteria such as Micrococcus, Bacillus, and Staphylococcus (MICs = 1-12.5 μg/ml), reduce proliferation of P. falciparum and Coccicdium protozoa, and also prevent replication of certain viruses.
• Uses: Poliether antibiotic. Coccidiostat. antifungal antibacterial Monensin sodium salt is used in potentiometric and spectroscopic studies of alkali metal ion complexes. Monensin (Na) is a polyether small molecule ionophore, capable of forming stable complexes to monovalent cations with specific affinity for Na+. Monensin presents a highly lipophilic scaffold around the bound ion, allowing movement of the complex through the lipid bilayer and consequent transport of the ion out of the cell. Excessive flux of ions out of the cell produces a cytotoxic effect and generates the antibiotic properties of Monensin.

Technology Process of Monensin, monosodium salt

There total 19 articles about Monensin, monosodium salt 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:

C36H61O11(1-) (76948-58-8) → monensin A sodium salt (22373-78-0)

Guidance literature:

With sodium cation; at 25 ℃; Thermodynamic data; ΔH^-, Γ^-, TΔS^-;

Reference yield:

monensin(1-) ion → monensin sodium salt (22373-78-0)

Guidance literature:

With sodium cation; In ethanol; at 25 ℃; Rate constant;

DOI:10.1021/ja00332a035

Reference yield:

monensin methyl ester (28636-21-7) → monensin sodium salt (22373-78-0)

Guidance literature:

Multi-step reaction with 5 steps

1: ZnCl₂

2: PCC / CH₂Cl₂

3: 1.) H₂ / 1.) Pd/C

4: 91 percent / K-Selectride / tetrahydrofuran

With hydrogen; potassium tri-sec-butyl-borohydride; pyridinium chlorochromate; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo00254a059

upstream raw materials:

C₃₆H₆₁O₁₁^(1-)

C₃₈H₆₆O₁₁

monensin methyl ester

(3R,5S,6S)-6-[(2R,3S,5R,2'S,5'R)-2'-Ethyl-5'-((S)-1-hydroxy-1-methyl-pent-4-ynyl)-3-methyl-octahydro-[2,2']bifuranyl-5-yl]-3,5-dimethyl-tetrahydro-pyran-2-one

Downstream raw materials:

monensin o-fluorobenzyl ester

monensin A benzyl ester

monensin benzyl ester

C₄₃H₇₇NO₁₃

Refernces

• 1、 Cox, B. G.,Truong, Ng van,Rzeszotarska, J.,Schneider, H.. "Rates and Equilibria of Alkali Metal and Silver Ion Complex Formation with Monensin in Ethanol". . p. 5965 - 5969. Retrieved 1984.
• 2、 Reynolds, Kevin A.,O'Hagan, David,Gani, David,Robinson, John A.. "BUTYRATE METABOLISM IN STREPTOMYCETES. CHARACTERIZATION OF AN INTRAMOLECULAR VICINAL INTERCHANGE REARRANGEMENT LINKING ISOBUTYRATE AND BUTYRATE IN STREPTOMYCES CINNAMONENSIS". . p. 3195 - 3208. Retrieved 2007/10/02.