Nigericin

Base Information

• Chemical Name: Nigericin
• CAS No.: 28380-24-7
• Molecular Formula: C40H68O11
• Molecular Weight: 724.96
• Hs Code.: 29419090
• European Community (EC) Number: 686-881-8
• UNII: RRU6GY95IS
• DSSTox Substance ID: DTXSID9041079
• Nikkaji Number: J19.064K
• Wikipedia: Nigericin
• Wikidata: Q7033077
• Metabolomics Workbench ID: 50012
• ChEMBL ID: CHEMBL405862
• Mol file: 28380-24-7.mol

Synonyms:Epinigericin;Nigericin;Pandavir

Chemical Property of Nigericin

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 183.5-185°
• Refractive Index: 1.543
• Boiling Point: 779.91 °C at 760 mmHg
• PKA: 4.39±0.10(Predicted)
• Flash Point: 226.927 °C
• PSA: 145.20000
• Density: 1.19 g/cm³
• LogP: 4.37090
• Storage Temp.: 2-8°C
• Solubility.: chloroform: 10 mg/mL, clear, colorless
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 9
• Exact Mass: 724.47616298
• Heavy Atom Count: 51
• Complexity: 1230

Purity/Quality:

99% ^*data from raw suppliers

Nigericin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC(OC1C(C)C(=O)O)CC2CC(C(C3(O2)C(CC(O3)(C)C4CCC(O4)(C)C5C(CC(O5)C6C(CC(C(O6)(CO)O)C)C)C)C)C)OC
• Isomeric SMILES: C[C@H]1CC[C@@H](O[C@H]1[C@@H](C)C(=O)O)C[C@@H]2C[C@H]([C@H]([C@@]3(O2)[C@@H](C[C@@](O3)(C)[C@H]4CC[C@@](O4)(C)[C@H]5[C@H](C[C@@H](O5)[C@@H]6[C@H](C[C@H]([C@@](O6)(CO)O)C)C)C)C)C)OC
• Uses: Nigericin is a polyether antibiotic produced by Streptomyces, notably S. hygroscopicus, isolated in the 1950s. Its complex structure was finally elucidated in 1968. Nigericin is an ionophore, possessing very high affinity for monovalent cations such as Na+ and K+. Nigericin disrupts membrane potential and Golgi apparatus in mitochondria. Although nigericin can be isolated as the free acid (under acidic conditions), like most ionophores it is extracted into organic solvents and is most conveniently isolated as a salt. In vitro, nigericin has broad biological activity against Gram positive bacteria, fungi, tumour cell lines and some viruses, including HIV. Nigericin is the most common member of the polyether class which are common false positives in in vitro screening bioassays using crude microbial extracts. They are thus important standards for dereplication.

Technology Process of Nigericin

There total 2 articles about Nigericin 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:

nigericin monosodium salt (28643-80-3) → nigericin (28380-24-7)

Guidance literature:

With perchloric acid; In chloroform; for 1h;

Reference yield:

→ nigericin (28380-24-7)

Guidance literature:

Reference yield:

nigericin (28380-24-7) → C46H72O11

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / dichloromethane / 6 h / 50 °C

2: triethylamine / dichloromethane / 12 h

With thionyl chloride; triethylamine; In dichloromethane;

DOI:10.1039/d0ra05137c

upstream raw materials:

nigericin monosodium salt

Downstream raw materials:

1,30-didehydroxy-1,30-dichloronigericinol