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Lasalocid
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Name

Lasalocid

 EINECS 247-401-9
CAS No. 25999-31-9 Density 1.119g/cm3
PSA 133.52000 LogP 5.84220
Solubility N/A Melting Point 110-114°; mp 100-109° (unsharp)
Formula C34H54 O8 Boiling Point 735.7°Cat760mmHg
Molecular Weight 590.798 Flash Point 224.8°C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 25999-31-9 (Lasalocid) Hazard Symbols N/A
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;

Article Data 10

Lasalocid Synthetic route

41733-86-2

lasalocid benzyl ester

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol Ambient temperature; Yield given;
With hydrogen; palladium on activated charcoal In ethanol for 3h; Ambient temperature;
67045-68-5

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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
25999-20-6

lasalocid sodium

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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; water0.75 g
73657-53-1

(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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
84911-92-2, 84985-23-9, 87678-43-1, 87678-51-1

(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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
84911-91-1

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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
31478-26-9, 87678-18-0

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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
75371-81-2, 84911-50-2, 84911-98-8

3-methyl-6-(3(R)-methyl-4,5-O-isopropylidenepentyl)salicylic acid methyl ester

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
73657-51-9

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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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
73657-52-0

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

25999-31-9

lasalocid (X 537 A)

Conditions
ConditionsYield
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

Lasalocid Chemical Properties

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.

Lasalocid Uses

It can be used as drugs, feed additives.

Lasalocid Toxicity Data With Reference

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.

Lasalocid Safety Profile

Poison by ingestion and intraperitoneal routes. An eye and skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

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