17090-79-8

Basic information

• Product Name: Monensin
• Synonyms: 2-(5-ethyltetrahydro-5-(tetrahydro-3-6-dioxaspiro(4.5)decane-7-butyricacid;a3823a;elancoban;gamma,2,8-tetramethyl--furyl)-2-furyl)-9-hydroxy-beta-methoxy-alph;monelan;Monensine sodium;4-[2-[2-Ethyl-5-(6-hydroxy-6-hydroxymethyl-3,5-dimethyltetrahydropyran-2-yl)-3-methyloctahydro-[2,2]bifuranyl-5-yl]-9-hydroxy-2,8-dimethyl-1,6-dioxaspiro[4.5]dec-7-yl]-3-methoxy-2-methylpentanoic acid;Monensin A
• CAS NO: 17090-79-8
• Molecular Formula: C₃₆H₆₂O₁₁
• Molecular Weight: 692.85
• EINECS: 244-941-7
• Product Categories: API's;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 17090-79-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 103-105°C
• Boiling Point: 608.24°C (rough estimate)
• Flash Point: 229.2 °C
• Appearance: Crystallin solid
• Density: 1.0773 (rough estimate)
• Vapor Pressure: 1.85E-25mmHg at 25°C
• Refractive Index: 1.5465 (estimate)
• Storage Temp.: 2-8°C
• PKA: 6.6 (in 66% DMF)
• CAS DataBase Reference: Monensin(CAS DataBase Reference)
• NIST Chemistry Reference: Monensin(17090-79-8)
• EPA Substance Registry System: Monensin(17090-79-8)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 36/37/39-45
• RIDADR: UN 3462 6.1/PG 2
• WGK Germany: 3
• RTECS: JH2830000
• HazardClass: 6.1(a)
• PackingGroup: II
• Hazardous Substances Data: 17090-79-8(Hazardous Substances Data)

Usage

Description

Monensin is a polyether antibiotic derived from Streptomyces cinnamonensis, first isolated in 1967. It is a broad-spectrum anticoccidial antibiotic with antifungal and antiviral properties. Monensin forms complexes with monovalent cations, such as Li+, Na+, K+, Rb+, Ag+, and Tl+, and functions as an Na+/H+ antiporter. It is known for its ability to block intracellular protein transport.

Uses

Used in Animal Health:
Monensin is used as a coccidiostat in the animal health industry to prevent coccidiosis, a parasitic disease affecting livestock. It also promotes growth and prevents bloat in animals.
Used in Ion Selective Electrodes:
Derivatives of monensin, such as monensin methyl ester and monensin decyl ester, are utilized in ion selective electrodes for their ability to complex with specific alkali metal cations, making them lipid-soluble and diffusible across membranes.
Used in Pharmaceutical Applications:
Monensin is used as a carboxylic acid, typically in its water-soluble sodium salt form (Coban, Rumensin), to treat histomoniasis, a disease caused by the protozoan parasite Histomonas meleagridis.
Used in the Chemical Industry:
Monensin is also used in the chemical industry as a crystalline solid due to its unique chemical properties and ability to form complexes with monovalent cations.
Brand Names:
Coban [as sodium salt] (Lilly)
Rumensin [as sodium salt] (Lilly)

Safety Profile

Poison by ingestion and intraperitoneal routes. An eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C37H64O10.Na/c1-11-35(32-21(4)18-27(43-32)29-20(3)17-22(5)37(41,12-2)46-29)14-13-28(44-35)34(9)15-16-36(47-34)19-26(38)23(6)31(45-36)24(7)30(42-10)25(8)33(39)40;/h20-32,38,41H,11-19H2,1-10H3,(H,39,40);/q;+1/p-1/t20-,21-,22+,23+,24+,25-,26-,27+,28+,29?,30+,31-,32?,34-,35-,36?,37-;/m0./s1

Upstream product

• 22373-78-0 monensin A sodium salt 

Downstream Products

• 126789-94-4 monensin dodecyl ester 
• 122651-63-2 C₄₅H₇₁NO₁₂ 
• 124901-21-9 C₄₈H₇₇NO₁₂ 
• 124901-22-0 C₅₁H₇₅NO₁₂ 
• 122629-96-3 C₅₅H₈₁NO₁₄ 
• 124901-20-8 C₄₄H₇₁NO₁₀ 
• 142525-13-1 C₄₆H₇₃NO₁₂ 
• 122629-89-4 2-monensinamidopropanoic acid benzyl ester 
• 122651-65-4 2-monensinamido-3-phenylpropanoic acid benzyl ester 
• 122629-94-1 monensinamidobutanedioic acid dibenzyl ester 
• 22373-78-0 Monensin sodium salt 
• 122629-92-9 3-(4-hydroxyphenyl)-2-monensinamidopropanoic acid benzyl ester 
• 122629-96-3 2-monensinamidopentanedioic acid dibenzyl ester 
• 124901-22-0 C₅₁H₇₅NO₁₂ 

Relevant articles and documents

Spectroscopic, semi-empirical and antimicrobial studies of a new amide of monensin A with 4-aminobenzo-15-crown-5 and its complexes with Na+ cation at 1:1 and 1:2 ratios

A new amide of monensin A with 4-aminobenzo-15-crown-5 (M-AM3) was synthesised and its ability to form complexes with Na+ cations was studied by ESIMS, 1H, 13C and 23Na NMR, FTIR and PM5 semi-empirical methods. ESI mass spectrometry indicates that in the gas phase M-AM3 amide forms complexes of 1:1 and 1:2 stoichiometry with Na + cations. The formation of such complexes is also confirmed in the acetonitrile solution, in which the existence of equilibrium between two structures A and B is found, of which B structure is dominant. The structures of M-AM3 and its 1:1 and 1:2 complexes with Na+ cations are stabilised by various intramolecular hydrogen bonds, which are discussed in detail. The in vitro biological tests have demonstrated that the new M-AM3 amide shows good activity towards some strains of Gram-positive bacteria (MIC 25-50 μg/ml).

1H, 13C NMR, FT-IR, ESI MS and PM5 studies of a new 3,6,9-trioxadecylamide of monensin A and its complexes with Li+, Na+ and K+ cations

A new 3,6,9-trioxadecylamide of monensin A (M-AM4) has been synthesised and its ability to form complexes with Li+, Na+ and K + cations has been studied by ESI mass spectrometry, 1H and 13C NMR, FT-IR spectroscopy and PM5 semiempirical method. The ESI MS data indicate that M-AM4 forms complexes with Li+, Na+ and K+ of exclusively 1:1 stoichiometry which are stable up to cv = 70 V. The formation of the M-AM4-Na+ is strongly favoured. Above cv = 70 the fragmentation process is observed. The spectroscopic studies show that the structures of the M-AM4 and its complexes with the cations of 1:1 stoichiometry are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The CO amide group is engaged in the complexation process of each cation. The M-AM4-K+ complex can also assume a structure in which the CO amide group does not participate in the complexation but the complexes of such structure do not dominate.

Spectroscopic, mass spectrometry, and semiempirical investigations of a new 2-(2-methoxyethoxy)ethyl ester of Monensin A and its complexes with monovalent cations

A new 2-(2-methoxyethoxy)ethyl ester of Monensin A (MON7) has been synthesized and its capability of complex formation with Li+, Na+, and K+ cations has been studied by ESI MS, 1H and 13C NMR, FT-IR, and PM5 semiempirical methods. ESI mass spectrometry indicates that MON7 forms complexes with Li+, Na+, and K+ of exclusively 1:1 stoichiometry which are stable up to cv = 70 V. The formation of complexes between MON7 and Na+ cations is strongly favored. Starting from about cv = 90 V fragmentation of the respective complexes is observed, primarily characterized by several dehydration steps. The structures of the MON7 complexes with Li+, Na+, and K+ cations are stabilized by intramolecular hydrogen bonds in which the OH groups are always involved. The structures are visualized and discussed in detail. It has been proved that the formation of a pseudo crown ring structure formed by MON7 is preferred in complexes with Na+ cations.