Name: Lasalocid
SKU: 25999-31-9

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Basic Information

Molecular Structure:
CAS No.:	25999-31-9
Name:	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

Conditions	Yield
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

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

: 25999-20-6
lasalocid sodium

: 25999-31-9
lasalocid (X 537 A)

Conditions

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

: 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

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

: 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

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

: 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

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

: 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

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

: 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

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

: 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

Yield

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

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

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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.

25999-31-9

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Chemistry

Uses

Toxicity Data With Reference

Safety Profile