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25999-31-9

Basic Information
CAS No.: 25999-31-9
Name: Lasalocid
Article Data: 10
Molecular Structure:
Molecular Structure of 25999-31-9 (Lasalocid)
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
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
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    Lasalocid

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    Lasalocid

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Chemistry

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.

Uses

It can be used as drugs, feed additives.

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.

Safety Profile

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