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CAS No.: | 25999-31-9 |
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Name: | Lasalocid |
Article Data: | 10 |
Molecular Structure: | |
Formula: | C34H54 O8 |
Molecular Weight: | 590.798 |
Synonyms: | 2,3-Cresoticacid,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]-,(-)- (8CI);Benzoic acid, 6-[7-[5-ethyl-5-(5-ethyltetrahydro-5-hydroxy-6-methyl-2H-pyran-2-yl)tetrahydro-3-methyl-2-furanyl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methyl-,[2R-[2a[2S*(3R*,4S*,5S*,7R*),3S*,5S*],5a,6b]]-;Antibiotic X 537A;Ionophore X 537A;Lasalocid;Lasalocid A;Lasalocide A;X 537A; |
EINECS: | 247-401-9 |
Density: | 1.119g/cm3 |
Melting Point: | 110-114°; mp 100-109° (unsharp) |
Boiling Point: | 735.7°Cat760mmHg |
Flash Point: | 224.8°C |
PSA: | 133.52000 |
LogP: | 5.84220 |
lasalocid benzyl ester
lasalocid (X 537 A)
Conditions | Yield |
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With hydrogen; palladium dihydroxide In ethanol Ambient temperature; Yield given; | |
With hydrogen; palladium on activated charcoal In ethanol for 3h; Ambient temperature; |
3-methyl-6-(3(R)-formylbutyl)salicylic acid benzyl ester
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme |
lasalocid sodium
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: dioxane 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme | |
With sulfuric acid; water In dichloromethane pH=1.5; | |
With sulfuric acid In dichloromethane; water pH=1.5; | |
With sulfuric acid In dichloromethane; water | 0.75 g |
(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
lasalocid (X 537 A)
Conditions | Yield |
---|---|
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 View Scheme | |
Multi-step reaction with 5 steps 1: 84 percent / PCC, 3A-MS / CH2Cl2 / Ambient temperature 2: tetrahydrofuran / 0 °C 3: PCC, 3A-MS / CH2Cl2 / Ambient temperature 5: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme |
(3RS,4S)-4-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>hexan-3-ol
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 2: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 3: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 3 steps 1: PCC, 3A-MS / CH2Cl2 / Ambient temperature 3: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme |
(2R)-2-<(2S,3S,5S)-5-ethyl-5-<(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyltetrahydropyran-2-yl>-3-methyltetrahydrofur-2-yl>butanal
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 2: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 3: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 4: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 4 steps 1: tetrahydrofuran / 0 °C 2: PCC, 3A-MS / CH2Cl2 / Ambient temperature 4: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme |
4(R)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>hexan-3-one
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 2: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme | |
Multi-step reaction with 2 steps 2: H2 / Pd(OH)2 / ethanol / Ambient temperature View Scheme |
3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: KH / tetrahydrofuran / 1.) 0 deg C, 20 min, 2.) 0 deg C, 1 h, 3.) room temperature, 0.5 h 2: 1.) BuLi, n-propanethiol / 1.) pentane, hexane, 0 deg C, 15 min, 2.) HMPA, 0 deg C, 10 min, room temperature, 45 min, 3.) room temperature, 2 h 3: 10percent HCl / H2O; tetrahydrofuran / 1.) room temperature, 4 h, 2.) 50 deg C, 7 h 4: 80 percent / NaIO4 / methanol; H2O / 2 h / Ambient temperature 5: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 6: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme |
benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(5(R)-ethyl-5-hydroxy-6(S)-methyl-2(R)-tetrahydropyranyl)-2(S)-tetrahydrofuryl>butyl ether
lasalocid (X 537 A)
Conditions | Yield |
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Multi-step reaction with 10 steps 1: 94 percent / oxalyl chloride, dimethyl sulfoxide, Et3N / CH2Cl2 / 1.) -60 deg C, 10 min, 2.) 15 min, 3.) warm to room temperature 2: 94 percent / n-BuLi / tetrahydrofuran; hexane / 1.) room temperature, 1 h, 2.) -78 deg C to room temperature, 10 h 3: NaHCO3, MCPBA / CH2Cl2 / 3 h / Ambient temperature 4: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 5: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 6: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 7: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 8: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 9: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 10: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme |
benzyl 2(S)-<5(S)-ethyl-3(S)-methyl-5-(3(R)-1,5-dioxo-4(S)-methylspiro<2.5>-6(R)-octyl)-2(S)-tetrahydrofuryl>butyl ether
lasalocid (X 537 A)
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 90 percent / CuI / pentane; diethyl ether / 1.) 0 deg C, 15 min, 2.) 3 h 2: 98 percent / Li, NH3 / tetrahydrofuran / 1 h / Heating 3: 78 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 4: 89 percent / tetrahydrofuran / 0.5 h / 0 °C 5: 90 percent / sodium acetate, pyridinium chlorochromate / CH2Cl2 / 2 h 6: 33.8 percent / LDA, ZnCl2 / diethyl ether / 0 °C 7: H2 / palladium on carbon / ethanol / 3 h / Ambient temperature View Scheme |
IUPAC Name: 6-[(3R,4S,5S,7R)-7-[(2S,3S,5S)-5-Ethyl-5-[(2R,5R,6S)-5-ethyl-5-hydroxy-6-methyloxan-2-yl]-3-methyloxolan-2-yl]-4-hydroxy-3,5-dimethyl-6-oxononyl]-2-hydroxy-3-methylbenzoic acid
Molecular Formula: C34H54O8
Molecular Weight: 590.78776g/mol
Freely Rotating Bonds: 16
Polar Surface Area: 89.52 Å2
Index of Refraction: 1.528
Molar Refractivity: 162.72 cm3
Molar Volume: 527.7 cm3
Polarizability: 64.5 ×10-24cm3
Surface Tension: 43.6 dyne/cm
Density: 1.119 g/cm3
Flash Point: 224.8 °C
Enthalpy of Vaporization: 112.66 kJ/mol
Boiling Point: 735.7 °C at 760 mmHg
Vapour Pressure: 1.01E-22 mmHg at 25°C
The Cas Register Number of Lasalocid is 25999-31-9 .The chemical synonyms of Lasalocid (CAS No.25999-31-9) are Lasalocid ; [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- ; Lasalocid a .The molecular structure of Lasalocid (CAS No.25999-31-9) is.
It can be used as drugs, feed additives.
1. | skn-rbt 100 mg/24H MLD | DCTODJ Drug and Chemical Toxicology. 8 (1985),451. | ||
2. | eye-rbt 50 mg MOD | DCTODJ Drug and Chemical Toxicology. 8 (1985),451. | ||
3. | ipr-rat LD50:8 mg/kg | DCTODJ Drug and Chemical Toxicology. 8 (1985),451. | ||
4. | orl-hor LD50:22 mg/kg | AJVRAH American Journal of Veterinary Research. 42 (1981),456. |
Poison by ingestion and intraperitoneal routes. An eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.