Salinomicina

Base Information

• Chemical Name: Salinomicina
• CAS No.: 53003-10-4
• Molecular Formula: C₄₂H₇₀O₁₁
• Molecular Weight: 751.011
• Hs Code.: 2309901000
• European Community (EC) Number: 258-290-1
• DSSTox Substance ID: DTXSID90860650
• Wikipedia: Salinomycin
• Mol file: 53003-10-4.mol

Synonyms:53003-10-4;Salinomycine [INN-French];Salinomycinum [INN-Latin];Salinomicina [INN-Spanish];HSDB 7032;AHR 3096;EINECS 258-290-1;K 364;C42-H70-O11;DTXSID90860650;(2R)-2-[(2R,5S,6R)-6-[(2S,3S,4S,6R)-6-[(3S,5S,7R,9S,10S,12R,15R)-3-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-15-hydroxy-3,10,12-trimethyl-4,6,8-trioxadispiro[4.1.57.35]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl]-5-methyloxan-2-yl]butanoic acid;AKOS032949878;SMP1_000269;LS-15443;FT-0630657;2-(6-{6-[2-(5-Ethyl-5-hydroxy-6-methyloxan-2-yl)-15-hydroxy-2,10,12-trimethyl-1,6,8-trioxadispiro[4.1.5~7~.3~5~]pentadec-13-en-9-yl]-3-hydroxy-4-methyl-5-oxooctan-2-yl}-5-methyloxan-2-yl)butanoic acid

Chemical Property of Salinomicina

Chemical Property:

• Appearance/Colour: white or light yellow crystalline powder
• Vapor Pressure: 1.04E-32mmHg at 25°C
• Melting Point: 112.5-113.5 °C
• Boiling Point: 839.2 °C at 760 mmHg
• PKA: 6.4 (DMF)
• Flash Point: 243.2 °C
• PSA: 164.04000
• Density: 1.18 g/cm³
• LogP: 4.85330
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥142.2 mg/mL in EtOH; ≥91.8 mg/mL in DMSO
• Water Solubility.: Soluble in methanol. Insoluble in water
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 12
• Exact Mass: 750.49181304
• Heavy Atom Count: 53
• Complexity: 1320

Purity/Quality:

99% ^*data from raw suppliers

Salinomycin ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1CCC(C(O1)C(C)C(C(C)C(=O)C(CC)C2C(CC(C3(O2)C=CC(C4(O3)CCC(O4)(C)C5CCC(C(O5)C)(CC)O)O)C)C)O)C)C(=O)O
• Uses: antibacterial Salinomycin is a polyether ionophore with broad spectrum Gram positive and anti-coccidial activity. Salinomycin has a high affinity for monovalent cations, particularly potassium. Salinomycin is used to control coccidia in animals and for growth promotion in ruminants. Recently, salinomycin has been shown to inhibit cancer stem cells and is >100 times more potent than taxol. While the mechanism of action is unknown, it was noted that among the 60,000 compounds screened, another monovalent ionophore, nigericin, and a chloride channel inhibitor, avermectin, were also active. Salinomycin was used as a standard in the development of LC-MS/MS method for detection of residual coccidiostats in egg and muscle samples. It was used to screen out CD44+CD24- mesenchymal-like subpopulation within breast carcinomas.

Technology Process of Salinomicina

There total 132 articles about Salinomicina 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: 72.0%

salinomycin (120330-27-0) → salinomycin (53003-10-4,120330-27-0,126574-63-8)

Guidance literature:

With 3 A molecular sieve; trifluoroacetic acid; In dichloromethane; for 0.333333h; Ambient temperature;

DOI:10.1248/cpb.37.1717

Reference yield:

salinomycin SV sodium salt (55721-31-8) → salinomycin (53003-10-4,120330-27-0,126574-63-8)

Guidance literature:

With sulfuric acid; In dichloromethane;

DOI:10.1016/j.bmcl.2012.05.081

Reference yield:

D-Glucose (2280-44-6) → salinomycin (53003-10-4,120330-27-0,126574-63-8)

Guidance literature:

Multi-step reaction with 11 steps

3: 99 percent / DMSO, (COCl)2, Et₃N / CH₂Cl₂

4: 96 percent / PPh₃ / benzene / 80 °C

5: 84 percent / n-BuLi / tetrahydrofuran / -78 °C

6: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) oxidation

7: 1.) camphorsulfonic acid, 2.) n-Bu₄NF / 1.) room temperature, 2.) dioxane-THF, 65 deg C

8: 88 percent / H₂ / Lindlar / methanol

9: 1.) DMSO,(COCl)2, Et₃N, 2.) CSA / 1.) CH₂Cl₂, 2.) CH₂Cl₂, room temperature

10: (C₆H₁₁)2NMgBr / methanol / -55 °C

11: DDQ / CH₂Cl₂ / 1.5 h / Ambient temperature; buffer (pH 6.86)

With n-butyllithium; oxalyl dichloride; bis(cyclohexyl)aminomagnesium bromide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)80703-0

upstream raw materials:

salinomycin

C₅₇H₈₄O₁₂

C₅₇H₈₄O₁₂

21-episalinomycin

Downstream raw materials:

C₄₈H₇₅NO₁₀

C₄₉H₇₇NO₁₀

Refernces

• 1、 Antoszczak, Michal,Augustynowicz-Kope, Ewa,Brzezinski, Bogumil,Huczyski, Adam,Maj, Ewa,Wietrzyk, Joanna,Napirkowska, Agnieszka,Stefaska, Joanna,Janczak, Jan. "Synthesis, anticancer and antibacterial activity of salinomycin N-benzyl amides". . p. 19435 - 19459. Retrieved 2015/03/13.
• 2、 Huczynski, Adam,Janczak, Jan,Stefanska, Joanna,Antoszczak, Michal,Brzezinski, Bogumil. "Synthesis and antimicrobial activity of amide derivatives of polyether antibiotic - Salinomycin". experimental part. p. 4697 - 4702. Retrieved 2012/08/13.