85956-22-5

Basic information

• Product Name: Pravastatin Lactone
• Synonyms: (2S)-2-Methyl-Butanoic Acid (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;R 414;(1S)-1β-[2-[[(2R,4R)-3,4,5,6-Tetrahydro-4β-hydroxy-6-oxo-2H-pyran]-2-yl]ethyl]-1,2,6,7,8,8aβ-hexahydro-2β-methyl-8α-[[(S)-2-methyl-1-oxobutyl]oxy]naphthalen-6β-ol;PRAVASTATIN SODIUM(RG);Pravastatin EP IMpurity D;Pravastatin IMpurity D;SQ 31369;Pravastatin class ester
• CAS NO: 85956-22-5
• Molecular Formula: C₂₃H₃₄O₆
• Molecular Weight: 406.51
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Chiral Reagents;Heterocycles
• Mol File: 85956-22-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 140-143°C
• Boiling Point: 590.537°C at 760 mmHg
• Flash Point: 199.475°C
• Appearance: /
• Density: 1.189g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.548
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• PKA: 13.49±0.40(Predicted)
• CAS DataBase Reference: Pravastatin Lactone(CAS DataBase Reference)
• NIST Chemistry Reference: Pravastatin Lactone(85956-22-5)
• EPA Substance Registry System: Pravastatin Lactone(85956-22-5)

Safety Data

• Hazardous Substances Data: 85956-22-5(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Powder

Uses

Different sources of media describe the Uses of 85956-22-5 differently. You can refer to the following data:
1. Pravastatin Lactone is a metabolite of Pravastatin (P702000).
2. lipid-lowering drugs

InChI:InChI=1/C23H34O6/c1-4-13(2)23(27)29-20-11-16(24)9-15-6-5-14(3)19(22(15)20)8-7-18-10-17(25)12-21(26)28-18/h5-6,9,13-14,16-20,22,24-25H,4,7-8,10-12H2,1-3H3/t13-,14-,16+,17?,18+,19-,20?,22-/m0/s1

Upstream product

• 81131-70-6 pravastatin sodium salt 
• 143842-74-4 <3R-<3α,5α(S^*)>>-8-methyl-3-(phenylmethoxy)-1-oxaspiro<4.5>dec-6-en-2-one 
• 143842-93-7 (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester 
• 143842-94-8 (S)-2-Methyl-butyric acid (1S,3S,5S,7S,8S,8aR)-3-(tert-butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R)-4-(tert-butyl-diphenyl-silanyloxy)-6-oxo-tetrahydro-pyran-2-yl]-ethyl}-5-hydroxy-7-methyl-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 143842-92-6 (S)-2-Methyl-butyric acid (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-yl ester 
• 143842-91-5 (1aS,3S,4S,4aS,5S,7S,8aR)-7-(tert-Butyl-diphenyl-silanyloxy)-4-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-3-methyl-octahydro-1-oxa-cyclopropa[d]naphthalen-5-ol 
• 143857-20-9 (1S,3R,7S,8S,8aR)-3-(tert-Butyl-diphenyl-silanyloxy)-8-{2-[(2R,4R,6S)-4-(tert-butyl-diphenyl-silanyloxy)-6-methoxy-tetrahydro-pyran-2-yl]-ethyl}-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-ol 
• 143842-90-4 Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,6S)-6-methoxy-4-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 143857-19-6 Acetic acid (1S,3R,7S,8S,8aR)-3-acetoxy-8-[2-((2R,4R,6S)-4-hydroxy-6-methoxy-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester 
• 143842-81-3 <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-N,N,2-trimethyl-6-(phenylmethoxy)-8-<(trimethylsilyl)oxy>-1-naphthaleneacetamide 
• 143842-80-2 <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-8-hydroxy-N,N,2-trimethyl-6-(phenylmethoxy)-1-naphthaleneacetamide 
• 143842-78-8 <1S-<1α,3(S^*),6α>>-3-<4-hydroxy-2-(phenylmethoxy)butyl>-N,N,6-trimethyl-2-cyclohexene-1-acetamide 
• 143842-87-9 <1S-<1α,2α,6α,8β,8aα>>-1,2,3,5,6,7,8,8a-octahydro-2-methyl-6-hydroxy-8-<(trimethylsilyl)oxy>-1-naphthalenepropionaldehyde 
• 143842-79-9 2-[(1S,6S)-3-((R)-2-Benzyloxy-4-oxo-butyl)-6-methyl-cyclohex-2-enyl]-N,N-dimethyl-acetamide 

Downstream Products

• 136590-28-8 R-195 
• 135716-16-4 (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 
• 136491-73-1 (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 
• 135716-15-3 (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 

Relevant articles and documents

Preparation method of oxidation impurities of hypolipidemic drugs

The invention discloses a preparation method of oxidation impurities of hypolipidemic drugs. The preparation method provided by the invention comprises the following step: in a solvent, under the action of an oxidizing agent and superfine silica powder, carrying out oxidation reaction as shown in the specification on a lactone compound as shown in a formula I to obtain a carbonyl compound as shown in a formula II. According to the preparation method disclosed by the invention, the superfine silica powder is adopted as a catalyst for oxidation reaction, so that the yield of the reaction is greatly improved.

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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.