NONACTIN

Base Information

• Chemical Name: NONACTIN
• CAS No.: 6833-84-7
• Molecular Formula: C40H64 O12
• Molecular Weight: 736.941
• Hs Code.: 29321900
• Mol file: 6833-84-7.mol

Synonyms:4,13,22,31,37,38,39,40-Octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone,2,5,11,14,20,23,29,32-octamethyl-,[1R-(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,29S*,32S*,34S*)]-(8CI); Nonactin (6CI,7CI);4,13,22,31,37,38,39,40-Octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane,nonactin deriv.; Ammonium ionophore I; NSC 52141; NSC 56409;[1R-(1R*,2R*,5R*,7R*,10S*,11S*,14S*,16S*,19R*,20R*,23R*,25R*,28S*,29S*,32S*,34S*)]-2,5,11,14,20,23,29,32-Octamethyl-4,13,22,31,37,38,39,40-octaoxapentacyclo[32.2.1.17,10.116,19.125,28]tetracontane-3,12,21,30-tetrone

Chemical Property of NONACTIN

Chemical Property:

• Melting Point: 147-148°
• Boiling Point: 890.6 °C at 760 mmHg
• Flash Point: 352.7 °C
• PSA: 142.12000
• Density: 1.041 g/cm³
• LogP: 6.02200
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: chloroform: soluble10mg/mL

Purity/Quality:

99% ^*data from raw suppliers

Nonactin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• General Description: Nonactin is a macrotetrolide antibiotic and ionophore known for its ability to selectively complex and transport monovalent cations, particularly potassium (K?) and ammonium (NH4?) ions, across biological membranes. It belongs to a class of naturally occurring cyclic polyethers produced by *Streptomyces* species, characterized by a 32-membered ring structure with alternating methyl and carbonyl groups. Nonactin's ionophoric properties make it useful in biochemical studies for modulating ion gradients and in sensor applications for detecting ammonium ions. Its mechanism involves encapsulating cations within its hydrophobic cavity, facilitating their passage through lipid bilayers. NONACTIN has also been explored for its antimicrobial activity, though its primary significance lies in its role as a model ionophore in membrane transport research.

Technology Process of NONACTIN

There total 33 articles about NONACTIN 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: 80.0%

C40H66O13 (159247-96-8) → nonactin (6833-84-7)

Guidance literature:

With dmap; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; In dichloromethane; at 20 ℃; for 19h;

DOI:10.1021/ol0609661

Reference yield: 52.0%

(+)-nonactyl-(-)-nonactic acid (91177-79-6) → nonactin (6833-84-7)

Guidance literature:

With dmap; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; In dichloromethane; for 12h; Ambient temperature;

DOI:10.1039/c39940002287

Reference yield:

(S)-2-((2S,5R)-5-((R)-2-(tert-butyldimethylsiloxy)propyl)tetrahydrofuran-2-yl)propanoic acid (159153-48-7) → nonactin (6833-84-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / DCC; DMAP / CH₂Cl₂ / 20 h / 20 °C

2: 99 percent / hydrogen / Pd/C / tetrahydrofuran / 5 h / 20 °C

3: 81 percent / 2,4,6-trichlorobenzoyl chloride; DMAP / CH₂Cl₂ / 47 h / 20 °C

4: 99 percent / hydrogen / Pd/C / tetrahydrofuran / 36 h / 20 °C / 760 Torr

5: 80 percent / 2,4,6-trichlorobenzoyl chloride; DMAP; molecular sieves 4 Angstroem / CH₂Cl₂ / 19 h / 20 °C

With dmap; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0609661

upstream raw materials:

sodium <1-(18)O2, 1-(13)C>propionate

(+)-nonactyl-(-)-nonactic acid

C₄₀H₆₆O₁₃

3-((4R,6R)-2,2,6-Trimethyl-[1,3]dioxan-4-yl)-propionaldehyde

Downstream raw materials:

Toluene-4-sulfonic acid (S)-2-[(2R,5S)-5-(2-oxo-propyl)-tetrahydro-furan-2-yl]-propyl ester

Refernces

A stereocontrolled synthesis of methyl (-)-nonactate

10.1055/s-2003-37129

The research aims to develop a stereoselective synthesis method for methyl (–)-nonactate, a key component in the production of nonactin, an antibiotic ionophore used in ion selective electrodes. The study explores the influence of olefin geometry on the stereoselectivity of iodoetherification, a crucial step in the synthesis. Key chemicals used include (E)-?-triethylsilyloxyalkene, generated from sulfone and (S)-2-benzyloxypropanal, which undergoes intramolecular iodoetherification in the presence of silver carbonate to form the key intermediate, cis-2,5-disubstituted tetrahydrofuran. (S)-2-benzyloxypropanal plays a pivotal role as a key reactant in the stereoselective synthesis process. It is used in the formation of (Z)-?-triethylsilyloxyalkene through a Wittig olefination reaction with phosphonium salt, which is derived from an alcohol intermediate. The researchers found that the geometry of the olefin significantly affects the stereoselectivity of the iodoetherification process, with trans-olefins yielding higher stereoselectivity. The study concludes that by carefully controlling the olefin geometry and using silver carbonate as a catalyst, a highly stereoselective synthesis of methyl (–)-nonactate can be achieved, paving the way for further total synthesis of nonactin.

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