79952-44-6

Basic information

• Product Name: Epi Lovastatin
• Synonyms: Epi Lovastatin;(2R)-2-Methylbutanoic acid (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 ester;Epilovastatin, 10 - 15% isoMers;Lovastatin epi-Isomer;Simvastatin EP Impurity F;(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2R)-2-methylbutanoate;(R)-(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2-methylbutanoate;Epilovastatin, 95%, 10 - 15% isomers
• CAS NO: 79952-44-6
• Molecular Formula: C24H36O5
• Molecular Weight: 404.53964
• Product Categories: Chiral Reagents;Heterocycles;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 79952-44-6.mol

Chemical Properties

• Melting Point: 108-110?C
• Boiling Point: 559.198°C at 760 mmHg
• Flash Point: 185.304°C
• Appearance: /
• Density: 1.12
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.532
• Storage Temp.: -20?C Freezer
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Epi Lovastatin(CAS DataBase Reference)
• NIST Chemistry Reference: Epi Lovastatin(79952-44-6)
• EPA Substance Registry System: Epi Lovastatin(79952-44-6)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 79952-44-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Epi Lovastatin is used as an impurity in the production of Lovastatin, an antihypercholesterolemic compound. It plays a crucial role in the synthesis and formulation of Lovastatin, which is used for lowering cholesterol levels in the blood and treating conditions related to high cholesterol, such as atherosclerosis and coronary heart disease.
Epi Lovastatin is also used as a reference standard for quality control and analytical purposes in the pharmaceutical industry. It helps ensure the purity, potency, and consistency of Lovastatin products, contributing to the overall safety and efficacy of the medication.

InChI:InChI=1/C24H36O5/c1-5-15(3)24(27)29-21-11-14(2)10-17-7-6-16(4)20(23(17)21)9-8-19-12-18(25)13-22(26)28-19/h6-7,10,14-16,18-21,23,25H,5,8-9,11-13H2,1-4H3/t14?,15?,16-,18+,19+,20-,21?,23-/m0/s1

Upstream product

• 75225-51-3 lovastatin acid 
• 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 
• 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 
• 117020-90-3 *),3α,7β,8β(2S^*,4S^*,6RS^*),8aβ>>-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-8-<2-(tetrahydro-4,6-dihydroxy-2H-pyran-2-yl)ethyl>-1-naphthalenyl 2-methylbutanoate 
• 314729-27-6 7-1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-(2-methylbutyryloxy)-1(S)-naphthyl-3(R),5(R)-dihydroxyheptanoic acid 
• 237073-64-2 Ammonium-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R),dimethyl-8(S)-(2-methylbutyryloxy)-1(S)-naphthyl]-3(R),5(R)-dihydroxyheptanoate 
• 102963-74-6 N-benzyl 7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2(S)-methylbutanoyl>oxy>-1(S)-naphthyl>-3(R)-<(tert-butyldimethylsilyl)oxy>-5(R)-hydroxyheptanoic acid amide 
• 103063-54-3 6(S)-<2-<8(S)-<<2(S)-methylbutanoyl>oxy>-2(S),6(R)-dimethyl-1,2,6,7,8,8a(R)-hexahydro-1(S)-naphthyl>ethyl>-4-(R)-<(tert-butyldimethylsilyl)oxy>-3,4,5,6-tetrahydro-2H-pyran-2-one 
• 158041-69-1 (3R,4aR,7S,8S,8aS)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 158041-68-0 (3R,4aR,7S,8S,8aR)-8-(tert-Butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one 
• 158041-67-9 (2Z,8E,10E)-(R)-1-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-dodeca-2,8,10-trien-4-one 
• 158041-79-3 (E)-(R)-3-(tert-Butyl-dimethyl-silanyloxy)-7-[(1S,2S,6S,8S,8aR)-2,6-dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-5-oxo-hept-6-enoic acid methyl ester 
• 158111-07-0 (R)-7-[(1S,2S,6S,8S,8aR)-2,6-Dimethyl-8-((S)-2-methyl-butyryloxy)-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl]-3-hydroxy-5-oxo-heptanoic acid methyl ester 
• 158041-77-1 (S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-8-(tert-butyl-dimethyl-silanyloxymethyl)-3,7-dimethyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 

Downstream Products

• 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 
• 75225-51-3 lovastatin acid 
• 151006-15-4 (4R,6R)-4-hydroxy-6-(2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)ethyl)tetrahydro-2H-pyran-2-one 
• 81189-92-6 (S)-2-methyl-butyric acid (3R,7S,8S,8aR)-8-{2-[(2R,4R)-4-acetoxy-6-oxo-tetrahydro-pyran-2yl]-ethyl}-3,7-dimetyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 105227-52-9 (S)-2-Methyl-butyric acid (1S,3R,7S,8S,8aR)-3,7-dimethyl-8-(2-{(2S,4R)-4-[2-(4-nitro-phenyl)-acetoxy]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester 
• 121009-77-6 simvastatin acid 
• 132748-10-8 (3R,5R)-3,5-dihydroxy-7-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid 
• 75225-50-2 lovastatin hydroxy acid sodium salt 
• 79902-31-1 (4R,6R)-6-[2-((1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthyl)ethyl]-4-[(tert-butyldimethylsilyl)oxy]-3,4,5,6-tetrahydro-2H-pyran-2-one 

Relevant articles and documents

Bioprospecting lovastatin production from a novel producer Cunninghamella blakesleeana

Beside anti-cholesterol activity, lovastatin garners worldwide attention for therapeutical application against various diseases especially cancer. A total of 36 filamentous fungi from soil samples were isolated and screened for lovastatin production by yeast growth bioassay method. C9 strain (later identified as Cunninghamella blakesleeana) was screened as potential strain of lovastatin production. Further confirmation of the compound was made using TLC, HPTLC and HPLC in which similar Rf value, densitogram peak and chromatogram peak against the standard lovastatin were observed, respectively. The purified lovastatin subjected for IR analysis showed a lactone ring peak at 1763.63?cm?1 similar to standard lovastatin. Further structural analysis including NMR and LC–MS of the purified lovastatin reassures the molecular formula and molecular weight similar to standard. In quantitative terms, C. blakesleeana, Aspergillus terreus and Aspergillus flavus produced 1.4?mg?g?1 DWS, 0.83?mg?g?1 DWS and 0.3?mg?g?1 DWS of lovastatin, respectively, (p 50: 145.9?μg?mL?1 (140?μL), and the percentage of inhibition is maximum at 199.5?μg/mL which is statistically significant (p 0.0001).

Drug or Supplement Combination with Conjugated Linoleic Acid for Fat Loss in Mammals

Food, feed or drug combinations with conjugated linoleic acid are described that cause enhanced fat loss in mammals more efficiently than any of the individual components of the combination. Food, feed, or drugs that activate AMP activated protein kinase, agonists of nuclear receptors that bind RXR in adipocytes, or statin inhibitors were found to be more effective for fat loss when combined with conjugated linoleic acid.

PROCESS FOR THE PURIFICATION OF LOVASTATIN

The invention relates to a process for the preparation of lovastatin. More particularly, it relates to the preparation of lovastatin substantially free of dihydrolovastatin. The invention also relates to pharmaceutical compositions that include the lovastatin substantially free of dihydrolovastatin and use of said compositions for treating hypercholesterolemia.

A METHOD FOR THE MANUFACTURE OF LOVASTATIN

A method for the manufacture of Lovastatin of formula (I) is disclosed. The method comprises of: A. lactonisation of Mevinolinic acid (II) and isolation of impure Lovastatin (I), B. purification of impure Lovastatin (I), C. optionally, repurification of pure Lovastatin (I) from a mixture of alumina and a water miscible solvent.

AN IMPROVED METHOD FOR MANUFACTURE OF 4-HYDROXY PYRAN-2-ONE DERIVATIVES

A process for preparation of 4-hydroxy-pyran-2-one derivative of formula (I), wherein R is (a), and wherein R1 and R2 are methyl and R3 is hydrogen or methyl, comprising the steps of, heating a compound of formula (II), wherein R is as defined before, and R4 is hydrogen, NH4+ or an alkali metal, in a solvent mixture consisting of an aromatic hydrocarbon and a ketone in an inert atmosphere at a temperature of between 60°C to 92°C in the absence or presence of orthophosphoric acid or its alkali dihydrogen salts or alkali hydrogen salts of a dibasic acid, followed by optional neutralization of the reaction mixture with an organic base and obtaining compound of formula (I) in high purity and substantially free of impurities through a step of isolation and crystallization. The process leads to formation of derivatives of formula (I) in high purity with dimmer impurity (III) less than 0.1% and anhydro impurity (IV) below 0.15%.

LACTONIZATION PROCESS

The instant invention discloses a process for preparation of compound of formula (II) comprising treatment of compound of formula (I) with sulphuric acid, wherein the sulphuric acid is added in one portion, at less than 0.8 equivalents of compound of formula (I); at a temperature less than -150 C; for a time less than 1 hour; in a water miscible solvent, preferably acetonitrile, where G = unsubstituted or substituted alkyl, aryl or hetero aryl and X = H or metal or amine.

FED BATCH SOLID STATE FERMENTATION FOR THE PRODUCTION OF HMG-COA REDUCTASE INHIBITORS

The present invention provides a novel method for producing compound of formula (I), its acid form or any salt form, where R1 is H or CH3, by solid state fermentation using fed-batch technique by culturing microorganisms capable of producing the compound of formula (I).

Treatment of type 1 diabetes with PDE5 inhibitors

The use of a PDE5 inhibitor without substantial PDE2 inhibiting activity, or a pharmaceutically acceptable salt thereof in the preparation of a medicament for the treatment of Type 1 Diabetes. A method of treating Type 1 Diabetes in an individual suffering from Type 1 Diabetes, which method comprises administering to said individual an effective amount of a PDE5 inhibitor without substantial PDE2 inhibiting activity, or a pharmaceutically acceptable salt thereof.

Method for producing pharmaceutical dosage forms

The invention relates to a method for producing a granulate while using spray-dried D-mannitol and to the production of pharmaceutical dosage forms comprised of granulates of this type. The invention additionally relates to granulates obtained by using this method and to pharmaceutical dosage forms, which contain statins, especially cerivastatin, and which can be produced from said granulates.

Highly purified simvastatin compositions

The present invention relates to a process to prepare semi synthetic statins, to intermediates formed during said process and to highly purified simvastatin produced by the process.