Lasalocid

Base Information

• Chemical Name: Lasalocid
• CAS No.: 25999-31-9
• Deprecated CAS: 37213-87-9,37259-88-4,26934-10-1,107684-72-0,802620-47-9
• Molecular Formula: C34H54 O8
• Molecular Weight: 590.798
• European Community (EC) Number: 247-400-3,247-401-9
• UNII: W7V2ZZ2FWB
• DSSTox Substance ID: DTXSID9048485
• Nikkaji Number: J28.607I
• Wikipedia: Lasalocid
• Wikidata: Q3827314
• NCI Thesaurus Code: C79131
• Metabolomics Workbench ID: 21338
• ChEMBL ID: CHEMBL145347
• Mol file: 25999-31-9.mol

Synonyms:Avatec;Lasalocid;Lasalocid A;Ro 2 2985;Ro 2-2985;Ro 22985;X-537A

Chemical Property of Lasalocid

Chemical Property:

• Vapor Pressure: 1.01E-22mmHg at 25°C
• Melting Point: 110-114°; mp 100-109° (unsharp)
• Boiling Point: 735.7°Cat760mmHg
• PKA: 3.15±0.39(Predicted)
• Flash Point: 224.8°C
• PSA: 133.52000
• Density: 1.119g/cm³
• LogP: 5.84220
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile,(Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 13
• Exact Mass: 590.38186868
• Heavy Atom Count: 42
• Complexity: 910

Purity/Quality:

99.9% ^*data from raw suppliers

Lasalocid A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C1C(CC(O1)(CC)C2CCC(C(O2)C)(CC)O)C)C(=O)C(C)C(C(C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O
• Isomeric SMILES: CC[C@H]([C@@H]1[C@H](C[C@@](O1)(CC)[C@H]2CC[C@@]([C@@H](O2)C)(CC)O)C)C(=O)[C@@H](C)[C@H]([C@H](C)CCC3=C(C(=C(C=C3)C)O)C(=O)O)O
• Description: Lasalocid is an ionophore antibiotic isolated from certain Streptomyces sp. and used in veterinary practice as a coccidiostat for gastrointestinal parasites. Lasalocid cytotoxicity targets cell metabolism, demonstrating EC50 values in the range of 7-20 μM in viability assays using chicken hepatoma LMH cells and rat myoblast L6 cells.
• Uses: Lasalocid is a polyether ionophore with potent antibacterial activity isolated from Streptomyces lasaliensis, first reported in 1951. Lasalocid was developed as an animal health product for treatment of coccidia. Lasalocid is able to form neutral complexes with monovalent and divalent cations and transport the ions through apolar phase (including lipid bilayer membranes). Interestingly, lasalocid can also transport larger organic cations, e.g. protonated dopamine. Lasalocid is an anticancer supplement agent comprising of polyether antibiotic for treating brain tumors, also inhibits mitochondrial GPD2 activity and elicits anti-proliferative effects on cancer cells.

Technology Process of Lasalocid

There total 56 articles about Lasalocid 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:

lasalocid sodium (25999-20-6) → lasalocid (X 537 A) (25999-31-9,37259-88-4)

Guidance literature:

Multi-step reaction with 2 steps

1: dioxane

2: H₂ / palladium on carbon / ethanol / 3 h / Ambient temperature

With hydrogen; palladium on activated charcoal; In 1,4-dioxane; ethanol;

DOI:10.1021/ja00345a055

Reference yield:

lasalocid benzyl ester (41733-86-2) → lasalocid (X 537 A) (25999-31-9,37259-88-4)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(00)98022-5

Reference yield:

(2S)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butan-1-ol (73657-53-1) → lasalocid (X 537 A) (25999-31-9,37259-88-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 2 h

2: 89 percent / tetrahydrofuran / 0.5 h / 0 °C

3: 90 percent / sodium acetate, pyridinium chlorochromate / CH₂Cl₂ / 2 h

4: 33.8 percent / LDA, ZnCl₂ / diethyl ether / 0 °C

5: H₂ / palladium on carbon / ethanol / 3 h / Ambient temperature

With hydrogen; sodium acetate; pyridinium chlorochromate; zinc(II) chloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane;

DOI:10.1021/ja00345a055

upstream raw materials:

lasalocid benzyl ester

3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester

lasalocid sodium

(2S)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butan-1-ol

Downstream raw materials:

lasalocid 2-naphthylmethyl ester

C₃₈H₆₃NO₇

C₆H₇N*C₃₄H₅₄O₈

lasalocid 1-naphthylmethyl ester

Refernces

• 1、 Huczyński, Adam,Janczak, Jan,Stefańska, Joanna,Rutkowski, Jacek,Brzezinski, Bogumil. "X-ray, spectroscopic and antibacterial activity studies of the 1:1 complex of lasalocid acid with 1,1,3,3-tetramethylguanidine". . p. 51 - 55. Retrieved 2010.
• 2、 Huczynski, Adam,Rutkowski, Jacek,Brzezinski, Bogumil,Bartl, Franz. "Synthesis, FT-IR, 1H, 13C NMR, ESI MS and PM5 studies of a new Mannich base of polyether antibiotic-Lasalocid acid and its complexes with Li+, Na+ and K+ cations". . p. 497 - 504. Retrieved 2013/03/14.