Pravastatin lactone

Base Information

• Chemical Name: Pravastatin lactone
• CAS No.: 85956-22-5
• Molecular Formula: C23H34 O6
• Molecular Weight: 406.519
• European Community (EC) Number: 642-154-7
• UNII: JBE3Z4192Q
• DSSTox Substance ID: DTXSID70235286
• Nikkaji Number: J384.840J
• Wikidata: Q27281422
• Mol file: 85956-22-5.mol

Synonyms:Pravastatin lactone;85956-22-5;(+)-Pravastatin lactone;UNII-JBE3Z4192Q;SQ-31369;JBE3Z4192Q;R-414;PRAVASTATIN EP IMPURITY D;[(1S,3S,7S,8S,8aR)-3-hydroxy-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate;Pravastatin sodium specified impurity D [EP];(1S,3S,7S,8S,8aR)-3-Hydroxy-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8ahexahydronaphthalen-1-yl (2S)-2-methylbutanoate;Butanoic acid, 2-methyl-, (1S,3S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-3-hydroxy-7-methyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-;Pravastatin sodium impurity, pravastatin lactone- [USP];(1S,3S,7S,8S,8aR)-3-Hydroxy-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-Methylbutanoate (Pravastatin Lactone);SCHEMBL12122532;BDBM86706;DTXSID70235286;CHEBI:145933;HMS2090H21;AKOS040755957;CS-O-30741;AB01275516-01;PRAVASTATIN SODIUM IMPURITY D [EP IMPURITY];Q27281422;PRAVASTATIN SODIUM IMPURITY, PRAVASTATIN LACTONE- [USP IMPURITY];(S)-((1S,3S,7S,8S,8aR)-3-hydroxy-8-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl) 2-methylbutanoate;Pravastatin Sodium Imp. D (EP);Pravastatin Imp. D (EP);(1S,3S,7S,8S,8aR)-3-Hydroxy-8-[2-[(2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl;Pravastatin Lactone;Pravastatin Sodium Impurity D;Pravastatin Impurity D

Chemical Property of Pravastatin lactone

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 140-143oC
• Boiling Point: 590.537°C at 760 mmHg
• PKA: 13.49±0.40(Predicted)
• Flash Point: 199.475°C
• PSA: 93.06000
• Density: 1.189g/cm³
• LogP: 2.92030
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 406.23553880
• Heavy Atom Count: 29
• Complexity: 668

Purity/Quality:

99%+, ^*data from raw suppliers

PravastatinLactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(=O)OC1CC(C=C2C1C(C(C=C2)C)CCC3CC(CC(=O)O3)O)O
• Isomeric SMILES: CC[C@H](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)O)O
• Uses: Pravastatin Lactone is a metabolite of Pravastatin (P702000). lipid-lowering drugs

Technology Process of Pravastatin lactone

There total 31 articles about Pravastatin lactone 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: 85.0%

(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (143842-95-9) → pravastatin lactone (85956-22-5)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; water; for 29h;

DOI:10.1021/jo00052a029

Reference yield:

pravastatin sodium salt (81131-70-6,81176-41-2,124917-23-3) → lactone form of C-6 epimer of pravastatin (85798-96-5) + pravastatin (81093-37-0,81131-74-0,250737-12-3) + pravastatin lactone (85956-22-5) + SQ 31906

Guidance literature:

pH=2; Acidic aq. solution;

Reference yield:

pravastatin sodium salt (81131-70-6,81176-41-2,124917-23-3) → pravastatin lactone (85956-22-5) + R-195 (136590-28-8) + SQ 31906

Guidance literature:

With water; at 50 ℃; for 504000h; Further Variations:; Reagents; pH-values; Product distribution;

DOI:10.1021/js980434g

upstream raw materials:

pravastatin

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

pravastatin sodium salt

(1S,4S)-1-((R)-2-Benzyloxy-but-3-enyl)-4-methyl-cyclohex-2-enol

Downstream raw materials:

(S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,4aS,7S,8S,8aS)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3-oxo-decahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

R-195

Refernces

• 1、 -. "Preparation method of oxidation impurities of hypolipidemic drugs". Paragraph 0053; 0068-0069. . Retrieved 2021/05/12.
• 2、 Nigovic, Biljana,Vegar, Ivana. "Capillary electrophoresis determination of pravastatin and separation of its degradation products". experimental part. p. 615 - 622. Retrieved 2009/12/03.