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Simvastatin ammonium salt is a metabolite of Simvastatin, which is a competitive inhibitor of HMG-CoA reductase. It is a white powder in its chemical form and is widely recognized for its pharmaceutical applications.

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  • Factory Supply 1-Naphthaleneheptanoic acid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-b,d-dihydroxy-2,6-dimethyl-, monoammonium salt,(bR,dR,1S,2S,6R,8S,8aR)- (9CI);

    Cas No: 139893-43-9

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  • 1-Naphthaleneheptanoicacid, 8-(2,2-dimethyl-1-oxobutoxy)-1,2,6,7,8,8a-hexahydro-b,d-dihydroxy-2,6-dimethyl-, ammonium salt (1:1), (bR,dR,1S,2S,6R,8S,8aR)-

    Cas No: 139893-43-9

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  • 139893-43-9 Structure
  • Basic information

    1. Product Name: Simvastatin ammonium salt
    2. 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
    3. CAS NO:139893-43-9
    4. Molecular Formula: C25H40O6*H3N
    5. Molecular Weight: 453.61
    6. EINECS: 1533716-785-6
    7. Product Categories: Inhibitors;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;HMG-CoA reductase;Chiral Reagents;Heterocycles;Metabolites & Impurities
    8. Mol File: 139893-43-9.mol
  • Chemical Properties

    1. Melting Point: 128-131°C
    2. Boiling Point: N/A
    3. Flash Point: N/A
    4. Appearance: /
    5. Density: N/A
    6. Vapor Pressure: 0.001Pa at 25℃
    7. Refractive Index: N/A
    8. Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
    9. Solubility: DMSO (Sparingly), Ethanol (Slightly), Methanol (Slightly), Water (Slightly)
    10. Water Solubility: 3.3g/L at 20℃
    11. BRN: 4836426
    12. CAS DataBase Reference: Simvastatin ammonium salt(CAS DataBase Reference)
    13. NIST Chemistry Reference: Simvastatin ammonium salt(139893-43-9)
    14. EPA Substance Registry System: Simvastatin ammonium salt(139893-43-9)
  • Safety Data

    1. Hazard Codes: Xi,T
    2. Statements: 36/37/38-64-52/53-40-61
    3. Safety Statements: 26-36-36/37/39-24/25-22-53
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 139893-43-9(Hazardous Substances Data)

139893-43-9 Usage

Uses

Used in Pharmaceutical Industry:
Simvastatin ammonium salt is used as a pharmaceutical agent for its role as a competitive inhibitor of HMG-CoA reductase. This function makes it a key component in the treatment of high cholesterol and related cardiovascular conditions.
Used in Drug Development:
Simvastatin ammonium salt is also used as a starting point for the development of new drugs targeting HMG-CoA reductase. Its properties as a metabolite of Simvastin provide a foundation for further research and innovation in the field of cholesterol management and cardiovascular health.
Used in Research Applications:
In the field of medical research, Simvastatin ammonium salt is utilized as a research tool to study the mechanisms of HMG-CoA reductase inhibition and its effects on cholesterol synthesis. This helps scientists better understand the underlying processes and develop more effective treatments for related health issues.

Check Digit Verification of cas no

The CAS Registry Mumber 139893-43-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,8,9 and 3 respectively; the second part has 2 digits, 4 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 139893-43:
(8*1)+(7*3)+(6*9)+(5*8)+(4*9)+(3*3)+(2*4)+(1*3)=179
179 % 10 = 9
So 139893-43-9 is a valid CAS Registry Number.

139893-43-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (07363)  Tenivastatin ammonium salt  analytical standard

  • 139893-43-9

  • 07363-25MG

  • 1,547.91CNY

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139893-43-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 13, 2017

Revision Date: Aug 13, 2017

1.Identification

1.1 GHS Product identifier

Product name Simvastatin Ammonium Salt

1.2 Other means of identification

Product number -
Other names azanium,(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

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:139893-43-9 SDS

139893-43-9Relevant articles and documents

For the preparation of simvastatin method

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, (2017/08/25)

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.

Lov-D acyltransferase mediated acylation

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Page/Page column 26; 27, (2016/08/17)

Methods for the improved acylation of chemical substrates using LovD acyltransferases, thioesters having acyl groups, and (i) thiol scavengers and/or (ii) precipitating agents are presented. An improved method for the production of simvastatin using (i) activated charcoal as a thiol scavenger and/or (ii) ammonium hydroxide as a precipitating agent is also presented.

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

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Paragraph 0044-0047, (2017/05/04)

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

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Page/Page column 10-12, (2009/07/18)

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.

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

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Page/Page column 3; 4, (2009/07/03)

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.

New synthesis of simvastatin

Singamsetty, Radha Krishna,Vujjini, Satish Kumar,Manne, Nagaraju,Venkata Naga, Brahmeshwara Rao Mandava,Himabindu, Vurimidi,Battacharya, Apurba,Ghanta, Mahesh Reddy,Bandichhor, Rakeshwar

experimental part, p. 4452 - 4459 (2009/04/11)

A noninfringing synthesis of simvastatin 1, starting from lovastatin 2, is presented. This synthesis features the protection of the free hydroxyl group of the lovastatin with 3,4-dihydro-2H-pyran (DHP) and opening of the lactone ring with n-BuNH2 to afford amide 4 as a key intermediate. Copyright Taylor & Francis Group, LLC.

Process for preparing simvastatin and intermediates thereof

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Page/Page column 12/1, (2010/11/27)

Novel processes for the preparation of simvastatin and intermediates of such processes. Preferred embodiments include the preparation of lovastatin amides, protected lovastatin amide derivatives, simvastatin dihydroxy acid amide derivatives, alkali salts, simvastatin dihydroxy acids, simvastatin ammonium salts, and simvastatin.

PROCESS FOR PREPARING SIMVASTATIN

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Page/Page column 9/2, (2010/11/27)

A process for preparing simvastatin, intermediate compounds, and a solid premix comprising simvastatin and butylated hydroxyanisole.

IMPROVED PROCESS FOR MANUFACTURING STATINS

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Page/Page column 7, (2010/11/27)

The present invention provides an improved process for manufacturing statins comprising the following steps (i) reacting lovastatin with butyl amine to produce lovastatin amide (ii) isolating lovastatin butylamide in solid form by crystallization, from organic solvent (iii) optionally subjecting to hydroxyl protection to get diprotected lovastatin butylamide, (iv) subjecting proteceted or unprotected amide so obtained to C-Methylation employing lithium pyrrolidide prepared in situ by reacting butyl lithium and pyrrolidine, isolating the title product by conventional methods, and converting to its pharmacologically acceptable salt by known methods.

PROCESS FOR PREPARING SIMVASTATIN FROM LOVASTATIN AMINE SALTS IN THREE STEPS

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Page/Page column 6-7, (2008/06/13)

The application describes a new process for preparing Simvastatin from Lovastatin amine salts in three steps. Lovastatin was hydrolysed to acid form and then isolated in the form of amine salt like cyclopropyl or t-octyl amine etc. The salts isolated were methylated directly without any protection and deprotection of hydroxy groups. The Simvastatin ammonium salt was produced directly, converted to Simvastatin by conventional methods and then purified to Simvastatin.

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