Acetyl simvastatin

Base Information

• Chemical Name: Acetyl simvastatin
• CAS No.: 145576-25-6
• Molecular Formula: C27H40O6
• Molecular Weight: 460.611
• Hs Code.: 2932206000
• European Community (EC) Number: 641-866-5
• UNII: 171OXS3HEK
• DSSTox Substance ID: DTXSID10163099
• Metabolomics Workbench ID: 155008
• Nikkaji Number: J2.092.418G
• Wikidata: Q27251852
• Mol file: 145576-25-6.mol

Synonyms:Acetyl simvastatin;4'-Acetyl Simvastatin;145576-25-6;Simvastatin Acetate;4-Acetylsimvastatin;4'-Acetylsimvastatin;Simvastatin acetate ester;171OXS3HEK;(1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-(Acetyloxy)-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-3,7-dimethyl-1,2,3,7,8,8ahexahydronaphthalen-1-yl 2,2-dimethylbutanoate;[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-acetyloxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] 2,2-dimethylbutanoate;Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-8-(2-((2R,4R)-4-(acetyloxy)tetrahydro-6-oxo-2H-pyran-2-yl)ethyl)-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl ester;Butanoic acid, 2,2-dimethyl-, (1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-(acetyloxy)tetrahydro-6-oxo-2H-pyran-2-yl]ethyl]-1,2,3,7,8,8a-hexahydro-3,7-dimethyl-1-naphthalenyl ester;UNII-171OXS3HEK;acetylsimvastatin;(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-(Acetyloxy)-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-Dimethylbutanoate (Simvastatin Acetate Ester);Simvastatin Imp. B (EP);Acetyl Simvastatin;(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-(Acetyloxy)-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl 2,2-Dimethylbutanoate;Simvastatin Acetate Ester;Simvastatin Impurity B;Simvastatin specified impurity B [EP];Simvastatin impurity, acetyl simvastatin- [USP];SIMVASTATIN IMPURITY-B;SCHEMBL661954;DTXSID10163099;ACETYL SIMVASTATIN [USP-RS];AKOS040732310;DB14648;HY-135405;CS-0112448;SIMVASTATIN IMPURITY B [EP IMPURITY];J-008126;Q27251852;SIMVASTATIN IMPURITY, ACETYL SIMVASTATIN- [USP IMPURITY]

Chemical Property of Acetyl simvastatin

Chemical Property:

• Vapor Pressure: 3.1E-13mmHg at 25°C
• Refractive Index: 1.519
• Boiling Point: 575.2 °C at 760 mmHg
• Flash Point: 243.2 °C
• PSA: 78.90000
• Density: 1.11 g/cm³
• LogP: 5.15640
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Ethyl Acetate (Slightly), Methan
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 460.28248899
• Heavy Atom Count: 33
• Complexity: 809

Purity/Quality:

97% ^*data from raw suppliers

4''-AcetylSimvastatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)OC(=O)C)C
• Isomeric SMILES: CCC(C)(C)C(=O)O[C@H]1C[C@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]3C[C@H](CC(=O)O3)OC(=O)C)C
• Uses: Simvastatin (S485000) impurity.

Technology Process of Acetyl simvastatin

There total 10 articles about Acetyl simvastatin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

C21H30O5 (145576-24-5) + α,α-dimethylbutanoic anhydride (29138-64-5) → simvastatin acetate (145576-25-6)

Guidance literature:

With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; acetonitrile; at 20 ℃; for 0.5 - 1h; Product distribution / selectivity;

Reference yield: 98.0%

acetic anhydride (108-24-7) + simvastatin (123049-81-0,79902-63-9) → simvastatin acetate (145576-25-6)

Guidance literature:

acetic anhydride; With pyridine; In dichloromethane; at 20 ℃; for 0.166667h; Inert atmosphere;

simvastatin; With dmap; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1002/anie.201814123

Reference yield: 83.2%

C21H30O5 (145576-24-5) + 2,2-dimethylbutanoyl chloride (5856-77-9) → simvastatin acetate (145576-25-6)

Guidance literature:

With pyridine; lithium bromide; Product distribution / selectivity;

upstream raw materials:

C₂₁H₃₀O₅

2,2-dimethylbutanoyl chloride

C₂₃H₃₂O₆

(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

Downstream raw materials:

simvastatin

simvastatin acid

anhydrosimvastatin

simvastatin ammonium salt