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[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure

Lasalocid Struktur
25999-31-9
CAS-Nr.
25999-31-9
Bezeichnung:
[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure
Englisch Name:
Lasalocid
Synonyma:
Lasalocid;Aids003766;Lasalocid A;Aids-003766;Ionophore X-537A;Antibiotic X-537A;X 537A, Lasalocid A;Nsc243046 (sodium salt);25999-20-6 (Sodium salt);6-{7-[(5S)-5-((6S,5R)-5-Ethyl-5-hydroxy-6-methylperhydro-2H-pyran-2-yl)-5-ethyl-3-methyloxolan-2-yl](4S,5S,3R,7R)-4-hydroxy-3,5-dimethyl-6-oxononyl}-2-hydroxy-3-methylbenzoic acid
CBNumber:
CB5875179
Summenformel:
C34H54O8
Molgewicht:
590.79
MOL-Datei:
25999-31-9.mol

[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure Eigenschaften

Schmelzpunkt:
110-114°; mp 100-109° (unsharp)
alpha 
D25 -7.55° (methanol)
Siedepunkt:
735.7±60.0 °C(Predicted)
Dichte
1.119±0.06 g/cm3(Predicted)
storage temp. 
-20°C Freezer, Under inert atmosphere
L?slichkeit
Acetonitrile,(Slightly), Methanol (Slightly, Sonicated)
Aggregatzustand
Solid
pka
3.15±0.39(Predicted)
Farbe
White to Off-White

Sicherheit

Toxizit?t LD50 in mice (mg/kg): 40 i.p. (Berger); also reported as LD50 in mice (mg/kg): 146 orally, 64 i.p., J. W. Westley, "Antibiotics (Polyether)" in Kirk-Othmer Encyclopedia of Chemical Technology Vol. 3 (Interscience, New York, 3rd ed., 1978) p 61

[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

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.

Verwenden

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.

Trademarks

Avatec [as sodium] [Veterinary] (Hoffmann-LaRoche); Bovatec [as sodium] [Veterinary] (Hoffmann-LaRoche).

Allgemeine Beschreibung

Lasalocid is one of the polyether ionophore antibiotics and was found in the culture broth of Streptomyces lasaliensis by Hoffmann-La Roche in 195. It shows activity against gram-positive bacteria, including Mycobacterium and Streptomyces, and also against anaerobic bacteria, but it has no activity against gramnegative bacteria or fungi. Lasalocid also shows strong anticoccidial activity, and it stimulates propionic acid formation in the rumen. It is used for prophylaxis and for therapy of coccidial infections in poultry and as a feed additive for growth promotion in cattle.

[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

[2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.

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25999-31-9([2R-[2α[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5α,6β]]-6-[7-[5-Ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylsure)Verwandte Suche:

  • Lasalocid
  • Lasalocid A
  • 25999-20-6 (Sodium salt)
  • 6-{7-[(5S)-5-((6S,5R)-5-Ethyl-5-hydroxy-6-methylperhydro-2H-pyran-2-yl)-5-ethyl-3-methyloxolan-2-yl](4S,5S,3R,7R)-4-hydroxy-3,5-dimethyl-6-oxononyl}-2-hydroxy-3-methylbenzoic acid
  • Aids003766
  • Aids-003766
  • Nsc243046 (sodium salt)
  • X 537A, Lasalocid A
  • [2R-[2alpha[2S*(3R*,4S*,5S*,7R*)3S*,5S*],5alpha,6beta]]-6-[7-[5-ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-3-methylsalicylic acid
  • Benzoic acid, 6-(3R,4S,5S,7R)-7-(2S,3S,5S)-5-ethyl-5-(2R,5R,6S)-5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yltetrahydro-3-methyl-2-furanyl-4-hydroxy-3,5-dimethyl-6-oxononyl-2-hydroxy-3-methyl-
  • Ionophore X-537A
  • Antibiotic X-537A
  • 25999-31-9
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