139893-43-9

Basic information

• Product Name: Simvastatin ammonium salt
• Synonyms: SIMVASTATIN AMMONIUM SALT;SIMVASTATIN HYDROXY ACID, AMMONIUM SALT;Ammonium (3R,5R)-7-[(1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutyryloxy)-1,2,6,7,8,8a-hexahydro-2,6-dimethyl-1-naphthyl]-3,5-dihydroxyheptanoate;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a;1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-,d-dihydroxy-2,6-dimethyl-, monoammonium salt, (R,dR,1S,2S,6R,8S,8aR)- (9CI);Simvastatin impurity A;(3R,5R)-7-((1S,2S,6R,8S,8aR)-8-(2,2-dimethylbutanoyloxy)-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoate ammonium salt;Simvastatin acid ammonium salt
• CAS NO: 139893-43-9
• Molecular Formula: C₂₅H₄₀O₆*H₃N
• Molecular Weight: 453.61
• EINECS: 1533716-785-6
• Product Categories: Inhibitors;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;HMG-CoA reductase;Chiral Reagents;Heterocycles;Metabolites & Impurities
• Mol File: 139893-43-9.mol
• Article Data: 15

Chemical Properties

• Melting Point: 128-131°C
• Appearance: /
• Vapor Pressure: 0.001Pa at 25℃
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility: 3.3g/L at 20℃
• BRN: 4836426
• CAS DataBase Reference: Simvastatin ammonium salt(CAS DataBase Reference)
• NIST Chemistry Reference: Simvastatin ammonium salt(139893-43-9)
• EPA Substance Registry System: Simvastatin ammonium salt(139893-43-9)

Safety Data

• Hazard Codes: Xi,T
• Statements: 36/37/38-64-52/53-40-61
• Safety Statements: 26-36-36/37/39-24/25-22-53
• WGK Germany: 3
• Hazardous Substances Data: 139893-43-9(Hazardous Substances Data)

Usage

Chemical Properties

White Powder

Uses

Different sources of media describe the Uses of 139893-43-9 differently. You can refer to the following data:
1. A competitive inhibitor of HMG-CoA reductase. A metabolite of Simvastin
2. A metabolite of Simvastin (S485000). A competitive inhibitor of HMG-CoA reductase.

Upstream product

• 5856-77-9 2,2-dimethylbutanoyl chloride 
• 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 
• 134970-30-2 N-butyl-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),5(R)-bis<(tert-butyldimethylsilyl)oxy>heptanoic acid amide 
• 134970-29-9 N-butyl-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),5(R)-dihydroxyheptanoic acid amide 
• 938063-63-9 methyl 3-[(2,2-dimethyl-1-oxobutyl)thio]propionate 
• 101314-97-0 simvastatin sodium salt 
• 77550-67-5 ammonium mevinolinic acid 
• 75330-75-5 lovastatin 
• 123049-81-0 simvastatin 
• 939809-60-6 C₃₂H₄₇NO₅ 
• 121009-77-6 simvastatin acid 
• 476305-26-7 N-benzyl-7-[1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-[[2,2-dimethylbutanoyl]oxy]-1(S)naphthyl]-3(R),5(R)-bis[(tert-butyldimethylsilyl)oxy]heptanoic acid amide 
• 134970-33-5 N-butyl-7-<1,2,6,7,8,8a(R)-hexahydro-2(S),6(R)-dimethyl-8(S)-<<2,2-dimethylbutanoyl>oxy>-1(S)-naphthyl>-3(R),5(R)-dihydroxyheptanoic acid amide 
• 145576-25-6 simvastatin acetate 

Downstream Products

• 476305-24-5 C₅₀H₇₆O₁₀ 
• 123049-81-0 simvastatin 
• 121009-77-6 simvastatin acid 

Relevant articles and documents

For the preparation of simvastatin method

The present invention discloses a simvastatin preparation method, which comprises using lovastatin and alkyl amine to prepare lovastatin amide, protecting the hydroxyl in the lovastatin amide molecules, carrying out methylation on the protected lovastatin amide to obtain protected simvastatin amide, carrying out deprotection, alkaline hydrolysis and ammonium salt forming on the protected simvastatin amide to obtain a simvastatin ammonium salt, and carrying out cyclization on the simvastatin ammonium salt to generate simvastatin. According to the present invention, the methyl cyclohexane is adopted as the methylation reaction solvent, such that the tetrahydrofuran consumption is reduced, the cost is reduced, the production safety is improved, and the solvent recovery and reuse process is simplified.

A simvastatin ammonium salt can be used for synthesizing process for the preparation of the acyl donor

The invention relates to a preparation method of acyl donor capable of synthesizing simvastatin ammonium salt, which comprises the following steps: in a nitrogen protective atmosphere, reacting 2-mercaptoethanol and 2,2-dimethyl butyryl chloride at -5 to +5 DEG C for 2-6 hours, reacting at 20-30 DEG C for 8-12 hours to generate 2,2-dimethylbutyric acid-2-sulfhydrylglycolate, reacting the 2,2-dimethylbutyric acid-2-sulfhydrylglycolate with acetyl chloride at 0-10 DEG C for 2-3 hours, and reacting at 20-30 DEG C for 6-12 hours to generate the simvastatin ammonium salt side chain acyl donor 2,2-dimethylbutyric acid-2-sulfhydrylethoxyglycolate. The method has the advantages of cheap and accessible synthesis raw materials and simple synthesis technique, and is easy to amplify; and the 2-mercaptoethanol is low in boiling point and easy to recycle and reuse, thereby reducing the pollution and further lowering the cost, and thus, the product has high competitive power.

ISOLATION AND RECOVERY OF SIMVASTATIN IN LACTONE FORM OR IN THE FORM OF AN ACID SALT FROM THE HARVESTED FERMENTATION BROTH

The present invention relates to a novel process for isolation and recovery of compounds such as biosynthetically produced simvastatin in either lactone form or in the form of its acid salt in high yield and purity, from microbial fermentation broth and isolating the said statin from harvested microbial broth.