Monensin

Base Information

• Chemical Name: Monensin
• CAS No.: 17090-79-8
• Deprecated CAS: 1392-52-5,802902-12-1,1174269-36-3,1192273-30-5
• Molecular Formula: C36H62O11
• Molecular Weight: 670.882
• European Community (EC) Number: 241-154-0
• UNII: 906O0YJ6ZP
• DSSTox Substance ID: DTXSID4048561
• Nikkaji Number: J39.488B
• Wikipedia: Monensin
• Wikidata: Q3493048
• NCI Thesaurus Code: C83971
• Metabolomics Workbench ID: 51392
• ChEMBL ID: CHEMBL256105
• Mol file: 17090-79-8.mol

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

Chemical Property of Monensin

Chemical Property:

• Appearance/Colour: Crystallin solid
• Vapor Pressure: 1.85E-25mmHg at 25°C
• Melting Point: 103-105 °C
• Refractive Index: 1.5465 (estimate)
• Boiling Point: 766.3 °C at 760 mmHg
• PKA: 6.6 (in 66% DMF)
• Flash Point: 229.2 °C
• PSA: 156.20000
• Density: 1.21 g/cm³
• LogP: 2.93820
• Storage Temp.: 2-8°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 10
• Exact Mass: 670.42921279
• Heavy Atom Count: 47
• Complexity: 1110

Purity/Quality:

98%, ^*data from raw suppliers

Monensin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Bacterial Toxins
• 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
• Isomeric SMILES: CC[C@]1(CC[C@@H](O1)[C@@]2(CC[C@@]3(O2)C[C@@H]([C@H]([C@H](O3)[C@@H](C)[C@H]([C@H](C)C(=O)O)OC)C)O)C)[C@H]4[C@H](C[C@@H](O4)[C@@H]5[C@H](C[C@H]([C@@](O5)(CO)O)C)C)C
• Uses: Monensin A is a polyether antibiotic first isolated from Streptomyces cinnamonensis in 1967. Monensin A is a broad-spectrum anticoccicidial antibiotic, also exhibiting antifungal and antiviral activity. Monensin A forms complexes with monovalent cations such as Li+, Na+, K+, Rb+, Ag+ and Tl+ and is thus able to transport these cations across lipid membranes of cells, playing an important role as an Na+/H+ antiporter. It blocks intracellular protein transport and is used in animals to prevent coccidiosis, promote growth and prevent bloat. Derivatives of monensin, monensin methyl ester and particularly monensin decyl ester, are used in ion selective electrodes. Poliether antibiotic. Coccidiostat Monensin (2) C36H62O11, a carboxylic acid which is used as its water-soluble sodium salt (Coban, Rumensin). Monensin is also used to treat histomoniasis. The polyether ionophoric antibiotics are capable of complexing and interfacing with specific alkali metal cations to render them lipid-soluble and diffusible across parasite mitochondrial membranes. Related useful polyether antibiotics are narasin and lasalocid (3, Lasalocid A, C34H54O8,).

Technology Process of Monensin

There total 2 articles about Monensin 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:

monensin A sodium salt (22373-78-0) → monensin (17090-79-8)

Guidance literature:

With sulfuric acid; In dichloromethane;

DOI:10.1016/j.molstruc.2007.08.004

Reference yield:

→ monensin (17090-79-8)

Guidance literature:

DOI:10.1021/ja00495a065

Reference yield: 97.0%

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt (1738-78-9) + monensin (17090-79-8) → 2-monensinamido-3-phenylpropanoic acid benzyl ester (122651-65-4)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 5 ℃; for 12h;

DOI:10.1248/cpb.36.4776

upstream raw materials:

monensin A sodium salt

Downstream raw materials:

monensin dodecyl ester

C₄₅H₇₁NO₁₂

C₄₈H₇₇NO₁₂

C₅₁H₇₅NO₁₂

Refernces

• 1、 Zahran, Elsayed M.,Gavalas, Vasileios,Valiente, Manuel,Bachas, Leonidas G.. "Can temperature be used to tune the selectivity of membrane ion-selective electrodes?". . p. 3622 - 3628. Retrieved 2010.
• 2、 ?owicki, Daniel,Huczyński, Adam,Ratajczak-Sitarz, Ma?gorzata,Katrusiak, Andrzej,Stefańska, Joanna,Brzezinski, Bogumil,Bartl, Franz. "Structural and antimicrobial studies of a new N-phenylamide of monensin A complex with sodium chloride". experimental part. p. 53 - 59. Retrieved 2009/09/30.