22373-78-0

Basic information

• Product Name: Monensin sodium salt
• Synonyms: 1,6-Dioxaspiro[4.5]decane-7-butyricacid,2-[5-ethyltetrahydro-5-[tetrahydro-3-methyl-5-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.-2,8-tetramethyl-,monosodiumsal;1,6-Dioxaspiro[4.5]decane-7-butyricacid,2-[5-ethyltetrahydro-5-[tetrahydro-3-methyl-5-[tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2H-pyran-2-yl]-2-furyl]-2-furyl]-9-hydroxy-.beta.-methoxy-.alpha.,.gamma.-2,8-tetramethyl-,monosodiumsalt;Coban;Coban45;gamma,2,8-tetramethyl--furyl)-2-furyl)-9-hydroxy-beta-methoxy-alphmonosod;methyl-5-(tetrahydro-6-hydroxy-6-(hydroxymethyl)-3,5-dimethyl-2h-pyran-2-yl)-2;monensin,monosodiumsalt;Monensin,monosodiumsalt(9CI)
• CAS NO: 22373-78-0
• Molecular Formula: C₃₆H₆₁O₁₁*Na
• Molecular Weight: 710.87
• EINECS: 244-941-7
• Product Categories: Organics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Inhibitors
• Mol File: 22373-78-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 267-269 C
• Boiling Point: 766.3 °C at 760 mmHg
• Flash Point: 229.2 °C
• Appearance: light cream amorphous powder
• Vapor Pressure: 4.13E-27mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in methanol at 50mg/ml
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 1 month.
• BRN: 4122200
• CAS DataBase Reference: Monensin sodium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Monensin sodium salt(22373-78-0)
• EPA Substance Registry System: Monensin sodium salt(22373-78-0)

Safety Data

• Hazard Codes: T,T+
• Statements: 25-26/27/28
• Safety Statements: 36/37/39-45-22
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: JH2830000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 22373-78-0(Hazardous Substances Data)

Usage

Description

Monensin sodium salt, a polyether ionophoric antibiotic, is produced by Streptomyces cinnamonensis. It is a naturally occurring ionophorous antibiotic that preferentially forms complexes with monovalent cations to enable transport across lipid membranes. Monensin sodium salt is a light cream amorphous powder and possesses 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.

Uses

Used in Pharmaceutical Industry:
Monensin sodium salt is used as an antibiotic for treating bacterial, fungal, and parasitic infections. It is effective against Gram-positive bacteria such as Micrococcus, Bacillus, and Staphylococcus, and can reduce the proliferation of P. falciparum and Coccicdium protozoa. Monensin sodium salt also prevents the replication of certain viruses.
Used in Poultry Production:
Monensin sodium salt is used as a coccidiostat in poultry production to prevent coccidiosis, a disease caused by protozoan parasites of the genus Eimeria.
Used in Anticancer Research:
Monensin sodium salt is used in potentiometric and spectroscopic studies of alkali metal ion complexes. It is a polyether small molecule ionophore, capable of forming stable complexes with monovalent cations, specifically with Na+. The cytotoxic effect produced by the excessive flux of ions out of the cell generates the antibiotic properties of Monensin, which can be explored for its potential in preventing the growth of colon cancer cells.
Used in Chemical Research:
Monensin sodium salt is used as a research tool in the study of ion transport and the effects of ionophore compounds on cell membranes and their potential applications in various fields.

Biochem/physiol Actions

Na+ ionophore; blocks glycoprotein secretion; may induce catecholamine secretion from chromaffin cells. Useful in potentiometric and spectroscopic studies of alkali metal ion complexes.

Purification Methods

Crystallise it from EtOH/H2O [Cox et al. J Am Chem Soc 107 4297 1985].

References

Aowicki and Huczynski (2013), Structure and antimicrobial properties of monensin A and its derivatives: summary of the achievements; Res. Int. 2013 742149 Kallen et al. (1993), Monensin inhibits synthesis of plasma membrane sphingomyelin by blocking transport of ceramide through the Golgi: evidence for two sites of sphingomyelin synthesis in BHK cells; Biophys. Acta 1166 305 Boss et al. (1984), Monensin-induced swelling of Golgi apparatus cisternae mediated by a proton gradient; J. Cell. Biol. 34 1 Mollenhauer et al. (1990), Alteration of intracellular traffic by monensin; mechanism, specificity and relationship to toxicity; Biophys. Acta 1031 225 Hafner et al. (2021), The Cardenolide Glycoside Acovenoside A Interferes with Epidermal Growth Factor Receptor Trafficking in Non-Small Cell Lung Cancer Cells; Pharmacol. 12 611657 Oh-Hashi et al. (2021), Comparative Analysis of CREB3 and CREB3L2 Protein Expression in HEK293 Cells; J. Mol. Sci. 22 2767

InChI:InChI=1/C36H62O11.Na/c1-10-34(31-20(3)16-26(43-31)28-19(2)15-21(4)36(41,18-37)46-28)12-11-27(44-34)33(8)13-14-35(47-33)17-25(38)22(5)30(45-35)23(6)29(42-9)24(7)32(39)40;/h19-31,37-38,41H,10-18H2,1-9H3,(H,39,40);/q;+1/p-1/t19-,20+,21+,22+,23+,24+,25-,26-,27+,28-,29-,30-,31-,33+,34-,35+,36-;/m0./s1

Upstream product

• 28636-21-7 monensin methyl ester 
• 116278-53-6 (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 
• 116278-57-0 (S)-2-[(2S,5R,2'R,3'S,5'R)-2-Ethyl-5'-((2S,3S,5R)-6-hydroxymethyl-6-methoxy-3,5-dimethyl-tetrahydro-pyran-2-yl)-3'-methyl-octahydro-[2,2']bifuranyl-5-yl]-hex-5-yn-2-ol 
• 116278-51-4 (S)-4-[(2S,5R,2'R,3'S,5'R)-5'-((7S,8S,10R)-8,10-Dimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-2-ethyl-3'-methyl-octahydro-[2,2']bifuranyl-5-yl]-4-hydroxy-pentanal 
• 21386-58-3 sodium <2-(2)H2>propionate 
• 71105-51-6 sodium <1-(13)C>isobutyrate 
• 17090-79-8 Monensin A 
• 116278-50-3 (2S,2'R,5'S,2''R,3''S,5''R)-5''-((7S,8S,10R)-8,10-Dimethyl-1,4,6-trioxa-spiro[4.5]dec-7-yl)-5'-ethyl-2,3''-dimethyl-hexahydro-[2,2';5',2'']terfuran-5-one 
• 73876-46-7 (2S,2'R,5'S,2''R,3''S,5''R)-5''-((2S,3S,5R)-3,5-Dimethyl-6-oxo-tetrahydro-pyran-2-yl)-5'-ethyl-2,3''-dimethyl-hexahydro-[2,2';5',2'']terfuran-5-one 
• 116278-49-0 C₄₄H₆₆O₁₁ 
• 116278-48-9 C₄₄H₆₈O₁₁ 
• 116278-59-2 C₄₃H₇₆O₁₀Si₂ 
• 116278-60-5 C₃₈H₆₄O₁₁ 
• 116278-56-9 (2S,5R,2'R,3'S,5'R)-2-Ethyl-5'-((2S,3S,5R)-6-methoxy-3,5-dimethyl-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-yl)-3'-methyl-5-((S)-1-methyl-1-trimethylsilanyloxy-pent-4-ynyl)-octahydro-[2,2']bifuranyl 

Downstream Products

• 91003-04-2 monensin 26-pyromellitate 
• 1297518-94-5 C₄₃H₇₇NO₁₃ 
• 2387-23-7 1,3-Dicyclohexylurea 
• 17090-79-8 monensin 
• 131973-40-5 monensin pentafluorobenzyl ester 
• 127648-49-1 monensin benzyl ester 
• 127648-49-1 monensin A benzyl ester 
• 131973-39-2 monensin o-fluorobenzyl ester 

Relevant articles and documents

Thermodynamics of Reaction in Heterogeneous Systems (Water-Organic Phases) between the Ionophore Monensin and Alkali-Metal Cations

Gibbs functions, enthalpies, entropies, and volumes of reaction for the reaction of bacterial ionophore monensin with alkali-metal cations in various water-organic biphasic solvent systems are obtained by using various experimental methods.In addition, weak but perceptible solubilization of the complexes formed is shown to occur in the aqueous phase.Their dissociation in water is studied.All the data are discussed in terms of structure and solvation of the variuos species.The selectivity sequence is not solvent dependent though the enthalpic and entropic contributions for different cations vary with the solvent system involved.On the basis of these data, both biological functional aspects and analytical aspects relevant to the testing of ionophores are discussed.

BIOSYNTHESIS OF THE POLYETHER ANTIBIOTIC MONENSIN-A. RESULTS FROM THE INCORPORATIONS OF LABELLED ACETATE AND PROPIONATE AS A PROBE OF THE CARBON CHAIN ASSEMBLY PROCESSES

The incorporation of sodium - and (S)--propionate into the polyether antibiotic monensin-A in cultures of Streptomyces cinnamonensis occurs with retention of label only at C-4 and C-6, whereas during the incorporation of sodium (R)-propionate the deuterium label is lost to the medium.These results are consistent with the formation of (S)-methylmalonyl-CoA from the labelled propionate by carboxylation of propionyl-CoA with loss of the 2-pro-R hydrogen.The (S)-methylmalonyl-CoA is subsequently incorporated into the antibiotic by a decarboxylative condensation occuring with overall inversion.The incorporations of sodium -and -acetates into monensin-A provide evidence for a pathway of metabolism leading to methylmalonyl-CoA that does not proceed via succinyl-CoA.Instead, acetyl-CoA may be processed via butyryl-CoA and isobutyryl-CoA, to afford (S)-methylmalonyl-CoA.

BUTYRATE METABOLISM IN STREPTOMYCETES. CHARACTERIZATION OF AN INTRAMOLECULAR VICINAL INTERCHANGE REARRANGEMENT LINKING ISOBUTYRATE AND BUTYRATE IN STREPTOMYCES CINNAMONENSIS

The incorporations of varicus carbon-13 and deuterium labelled forms of isobutyrate into the polyether antibiotic monensin-A have provided evidence for the existence of a novel rearrangement in whole cells of Streptomyces cinnamonensis, which leads to the conversion of isobutyrate into butyrate.This rearrangement is shown to proceed in an intramolecular fashion by migration of the carboxy carbon of isobutyrate to the 2-pro-S methyl, with a concomitant back migration of a hydrogen atom from this methyl group predominantly into the 3-pro-R position in butyrate.Formally, therefore, the carboxy carbon is replaced with overall retention of configuration, in a vicinal interchange rearrangement.The significance of these observations with regard to the coenzyme requirements of the rearrangement, and its relationship to polyether and macrolide antibiotic production in Streptomycetes is discussed.