CAS No.75330-75-5,Lovastatin Suppliers

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Basic Information

Molecular Structure:
CAS No.:	75330-75-5
Name:	Lovastatin
Article Data:	18

Formula:	C₂₄H₃₆O₅
Molecular Weight:	404.547
Synonyms:	MK-803;Belvas;(1S-(1alpha(R),3alpha,7beta,8beta(2S,4S),8abeta))-(1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthyl) 2-methylbutanoate;Rodatin;Paschol;Artein;Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-(2-(tetrahydro-4-hydroxy-6-- oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1alpha(R),3alpha,7beta,8beta(2S,4S*),8abeta))-;Sivlor;MK 803;Mevinolin;Prestwick_819;Antibiotic MB 530B;Lestatin;Colevix;Lovastation;Mevinacor;Lovasterol;[(1S,3R,7R,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;2-Methyl-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1-naphthalenyl ester butanoic acid;Hipolip;Tecnolip;Lovastatine [French];6-alpha-Methylcompactin;MSD 803;Cholestra;Lovastatin (USP);ML-530B;Monacolin K;Hipovastin;Taucor;Mevacor (TN);[(1S,3R,7R,8S,8aR)-8-[2-[(4R)-4-hydroxy-6-oxo-oxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;Teroltrat;Lozutin;Lipofren;Lipdip;
EINECS:	616-212-7
Density:	1.12 g/cm³
Melting Point:	175 °C
Boiling Point:	559.2 °C at 760 mmHg
Flash Point:	185.3 °C
Solubility:	0.0004 mg/mL at 25 °C in water
Appearance:	White solid
Hazard Symbols:	Xi
Risk Codes:	36/37/38
Safety:	22-24/25-36/37/39-26
Transport Information:	UN 3077
PSA:	72.83000
LogP:	4.19550

Synthetic route

: 79691-11-5
6(R)-<2-<1,2,6,7,8,8a(R)-Hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutyryl>oxy>-1(S)-naphtyl>ethyl>-3,4,5,6-tetrahydro-4(R)-<(tert-butyldimethylsilyl)oxy>-2H-pyran-2-one

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
With hydrogen fluoride In acetonitrile at 25℃; for 1.4h;	94%
With hydrogen fluoride In acetonitrile at 0℃; for 5h;	77%
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran
With tetrabutyl ammonium fluoride; acetic acid In tetrahydrofuran for 18h; Ambient temperature;

: ammonium mevinolinic acid

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Stage #1: ammonium mevinolinic acid With phosphoric acid In toluene; butanone at 20 - 82℃; for 2 - 2.5h; Stage #2: With triethylamine In water; toluene; butanone at 20℃;	78.2%
With sulfuric acid In acetonitrile at -22 - -17℃; for 0.5h;

: 117020-90-3, 117066-28-1

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
With Celite; silver carbonate In toluene at 85 - 95℃; for 1h;	77%
With Celite; toluene; silver carbonate In toluene at 90℃; for 1h;	77%

: 75225-51-3, 137767-34-1
lovastatin acid

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
With phosphoric acid In water; toluene at 20 - 55℃; for 19h; pH=3.5; Product distribution / selectivity;	76.12%
With trifluoroacetic acid In ethyl acetate for 0.166667h;

: 85614-12-6
(S)-2-Methyl-butyric acid (1S,3S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 2: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 3: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

: 153079-18-6
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-4-chloro-6-formyloxy-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: imidazole / acetonitrile / 25 °C 2: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C 3: 92 percent / PDC / toluene / 0.33 h / 80 °C 4: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C 5: 65 percent / tetrahydrofuran / -78 °C 6: H+ / CHCl3 7: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 8: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 9: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: imidazole / acetonitrile / 25 °C
2: Ti(OiPr)4 / propan-2-ol / 0.5 h / 60 °C
3: 92 percent / PDC / toluene / 0.33 h / 80 °C
4: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
5: 65 percent / tetrahydrofuran / -78 °C
6: H+ / CHCl3
7: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
8: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
9: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme

: 153079-17-5
2-methyl-butyric acid 8-{2-[4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-6-oxo-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 65 percent / tetrahydrofuran / -78 °C 2: H+ / CHCl3 3: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 4: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 5: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

: 153079-20-0
(S)-2-Methyl-butyric acid (1S,4S,6S,7R,8S,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-6-hydroxy-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 92 percent / PDC / toluene / 0.33 h / 80 °C 2: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C 3: 65 percent / tetrahydrofuran / -78 °C 4: H+ / CHCl3 5: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 6: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 7: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

Yield

Multi-step reaction with 7 steps
1: 92 percent / PDC / toluene / 0.33 h / 80 °C
2: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C
3: 65 percent / tetrahydrofuran / -78 °C
4: H+ / CHCl3
5: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C
6: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C
7: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C
View Scheme

: 153079-22-2
(S)-2-Methyl-butyric acid (1S,3R,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3,7-dimethyl-6-oxo-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: H+ / CHCl3 2: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 3: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 4: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

: 153079-21-1
(S)-2-Methyl-butyric acid (1S,4S,7R,8R,8aR)-8-{2-[(2R,4R)-4-(tert-butyl-dimethyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-4-chloro-7-methyl-6-oxo-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester

: 75330-75-5
lovastatin

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 78 percent / AgOTf/2,6-di-tert-butyl-4-methylpyridine / 24 h / 25 °C 2: 65 percent / tetrahydrofuran / -78 °C 3: H+ / CHCl3 4: 2,6-di-tert-butyl-4-methylpyridine / CH2Cl2 / 0.25 h / 0 °C 5: 70 percent / Pd(OAc)2, HCOOH, Bu3N, Ph3P / dimethylformamide / 1 h / 60 °C 6: 94 percent / 48 percent HF / acetonitrile / 1.4 h / 25 °C View Scheme

Raw Materials

Downstream Products

75-65-0

67-64-1

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Chemistry

Structure of Lovastatin (CAS NO.75330-75-5):

Empirical Formula: C₂₄H₃₆O₅
Molecular Weight: 404.5396
IUPAC Name: [(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
Index of Refraction: 1.531
Molar Refractivity: 111.71 cm³
Molar Volume: 360.6 cm³
Polarizability: 44.28×10^-24cm³
Surface Tension: 43.5 dyne/cm
Density: 1.12 g/cm³
Flash Point: 185.3 °C
Enthalpy of Vaporization: 96.69 kJ/mol
Melting Point: 175°C
Boiling Point: 559.2 °C at 760 mmHg
Vapour Pressure: 7.81E-15 mmHg at 25°C
Water Solubility: 0.0004 mg/mL at 25 ºC
Physical Appearance: White Solid
Product Categories: Antibiotics ; APIs ; Intermediates & Fine Chemicals ; Pharmaceuticals ; API's ; HMG-CoA reductase

History

Lovastatin (CAS NO.75330-75-5) was isolated from the fungus Aspergillus terreus ,in August 1987 ,it was the first statin approved by the FDA.
In 1998, the FDA (US Food and Drug Administration ) placed a ban on the sale of dietary supplements derived from red yeast rice, which naturally contains lovastatin, arguing that products containing prescription agents require drug approval.

Uses

Lovastatin (CAS NO.75330-75-5) can be used as hypolipidemic agent for lowering cholesterol in those with hypercholesterolemia and so preventing cardiovascular disease.In plant physiology Lovastatin (CAS NO.75330-75-5) also has occasionally been used as inhibitor of cytokinin biosynthesis.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	17mg/kg/3W-I (17mg/kg)	BEHAVIORAL: WAKEFULNESS	Lancet. Vol. 343, Pg. 973, 1994.
human	TDLo	oral	8750ug/kg/14D (8.75mg/kg)	BEHAVIORAL: WAKEFULNESS BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)	Clinical Pharmacology and Therapeutics Vol. 50, Pg. 730, 1991.
man	TDLo	oral	240mg/kg/60W- (240mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS	Annals of Pharmacotherpy. Vol. 26, Pg. 190, 1992.
mouse	LD50	oral	> 1gm/kg (1000mg/kg)		Journal of Antibiotics. Vol. 32, Pg. 852, 1979.
women	TDLo	oral	285mg/kg/30W- (285mg/kg)	LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), ZONAL" LIVER: LIVER FUNCTION TESTS IMPAIRED SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Israel Journal of Medical Sciences. Vol. 28, Pg. 101, 1992.

Safety Profile

Hazard Codes of Lovastatin (CAS NO.75330-75-5): Irritant Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-36/37/39-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: 3077
WGK Germany: 3
RTECS: EK7907000
HazardClass: 9
PackingGroup: III

Specification

Lovastatin , its cas register number is 75330-75-5. It also can be called (1S,3R,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-3,7-dimethyl-8-(2-(2R,4R)-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl (S)-2-methyl-butyrate ; (S)-2-Methylbutyric acid, 8-ester with (4R,6R)-6-(2-((1S,2S,6R,8S,8aR)-1,2,6,7,8,8a-hexahydro-8-hydroxy-2,6-dimethyl-1-naphthyl)ethyl)tetrahydro-4-hydroxy-2H-pyran-2-one ; 6-alpha-Methylcompactin ; 6alpha-Methylcompactin ; Cholestra ;
Lipivas ; Lipofren ; Lovalip; Lovalord ; Lovasterol ; Mevinacor ; Mevinolin ; Mevlor ; Monacolin K ; Nergadan ; Paschol ; Rodatin .

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