1192-42-3

Basic information

• Product Name: MEVALONATE
• Synonyms: MEVALONATE;2,4-Dihydroxy-2-methylbutyric acid γ-lactone;2-Hydroxy-2-methylbutanolide;Dihydro-3-hydroxy-3-methyl-2(3H)-furanone;R,S-Mevalonolactone
• CAS NO: 1192-42-3
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.12
• Mol File: 1192-42-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 105-106 °C(Press: 5 Torr)
• Appearance: /
• Density: 1.266±0.06 g/cm3(Predicted)
• PKA: 13.14±0.20(Predicted)
• CAS DataBase Reference: MEVALONATE(CAS DataBase Reference)
• NIST Chemistry Reference: MEVALONATE(1192-42-3)
• EPA Substance Registry System: MEVALONATE(1192-42-3)

Safety Data

• Hazardous Substances Data: 1192-42-3(Hazardous Substances Data)

Usage

General Description

Mevalonate is a key intermediate in the synthesis of isoprenoids, a large and diverse group of natural products that include cholesterol, steroids, and various hormones. It is synthesized from acetyl-CoA through a series of enzymatic reactions in the mevalonate pathway, which is crucial for the biosynthesis of important cellular components such as dolichol, ubiquinone, and heme A, as well as for the production of isoprenoid-derived metabolites. Mevalonate is also a precursor for the synthesis of squalene, a key intermediate in the biosynthesis of cholesterol and steroid hormones. Given its pivotal role in cellular metabolism, mevalonate and its derivatives have been identified as potential targets for the development of novel drugs for various diseases, including cancer, cardiovascular disorders, and metabolic syndromes.

Upstream product

• 252575-70-5 (2R,5S,6R)-2-(2-Hydroxy-ethyl)-2,4,5-trimethyl-6-phenyl-morpholin-3-one 
• 252575-66-9 ((2R,5S,6R)-2,4,5-Trimethyl-3-oxo-6-phenyl-morpholin-2-yl)-acetaldehyde 
• 207223-25-4 2R,5S,6R-2,4,5-trimethyl-2-(2-propenyl)-6-phenyl-morpholin-3-one 
• 266694-67-1 Benzoic acid (R)-3-hydroxy-3-((2R,4aR,7R,8aR)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-butyl ester 
• 590-90-9 1-Hydroxy-3-butanone 
• 151-50-8 potassium cyanide 
• 6322-49-2 4-chloro-2-butanone 

Downstream Products

• 22122-36-7 3-methyl-5H-furan-2-one 
• 33693-67-3 α-bromo-α-methyl-γ-butyrolactone 

Relevant articles and documents

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Enantioselective syntheses of substituted γ-butyrolactones

The previously described chiral 2-acyloxathianes 5 (Scheme I) are used in two different enantioselective syntheses of γ-butyrolactones. In one synthesis, Grignard addition, cleavage and reduction to carbinols RR'C(OH)CH2OH is followed by tosylation, malonate homologation, lactonization, and removal of the carbomethoxy group to give optically active γ-lactones. A modification of this synthesis (Scheme I) leads to optically active α-methylene-γ-lactones. In the second synthesis, reaction of a bromomagnesium enolate with ketones 5 leads to β-hydroxyesters, which, by appropriate sequences of reduction and cleavage (Scheme II) are converted to optically active α- or β-hydroxy-γ-lactones.

Preparation of α-Hydroxy-γ-lactones and their Application in the Synthesis of α,β-Butenolides, α-Alkylidene-γ-lactones and Furans

A straightforward synthesis of α-hydroxy-γ-butyrolactones was carried out by condensation reaction of the lithium anion of ethoxyethyl-protected cyanohydrins with epoxides, followed by acidic treatment.Synthetic applications of these synthons in the preparation of interesting α,β-butenolides, α-alkylidene-γ-lactones and furans are described.