2381-87-5

Basic information

• Product Name: Dehydromevalonolactone
• Synonyms: 5,6-Dihydro-4-methyl-2H-pyran-2-one;Dehydromevalonolactone;Δ2-Anhydromevalonic lactone;2H-Pyran-2-one,5,6-dihydro-4-methyl-
• CAS NO: 2381-87-5
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.1265
• Mol File: 2381-87-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 234.8°Cat760mmHg
• Flash Point: 89.7°C
• Appearance: /
• Density: 1.065g/cm³
• Vapor Pressure: 0.0518mmHg at 25°C
• Refractive Index: 1.464
• CAS DataBase Reference: Dehydromevalonolactone(CAS DataBase Reference)
• NIST Chemistry Reference: Dehydromevalonolactone(2381-87-5)
• EPA Substance Registry System: Dehydromevalonolactone(2381-87-5)

Safety Data

• Hazardous Substances Data: 2381-87-5(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 104, p. 5486, 1982 DOI: 10.1021/ja00384a040The Journal of Organic Chemistry, 49, p. 1647, 1984 DOI: 10.1021/jo00183a030

InChI:InChI=1/C6H8O2/c1-5-2-3-8-6(7)4-5/h4H,2-3H2,1H3

Upstream product

• 87894-65-3 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride 
• 674-26-0 mevalonolactone 
• 1443-80-7 4-cyanophenyl methyl ketone 

Downstream Products

• 111392-93-9 Acetic acid (S)-3,5-dihydroxy-3-methyl-1-phenethyl-pentyl ester 
• 111392-91-7 (S)-1-(tert-Butyl-dimethyl-silanyloxy)-3-methyl-7-phenyl-heptane-3,5-diol 
• 111466-33-2 (4R,6S)-4-Hydroxy-4-methyl-6-phenethyl-tetrahydro-pyran-2-one 
• 111466-31-0 (4R,6R)-4-Hydroxy-4-methyl-6-phenethyl-tetrahydro-pyran-2-one 
• 372-42-9 3-methylpent-2-enedioic acid 
• 4457-71-0 3-methylpentane-1,5-diol 
• 29293-06-9 3-methylpent-2-ene-1,5-diol 
• 1392278-17-9 5-hydroxy-N-methoxy-N,3-dimethyl-3-phenylpentanamide 
• 1259930-17-0 (R)-4-methyl-4-phenyltetrahydro-2H-pyran-2-one 
• 1392278-10-2 (S)-4-methyl-4-phenyltetrahydro-2H-pyran-2-one 
• 1121-84-2 4-methyl-tetrahydro-pyran-2-one 

Relevant articles and documents

PROCESSES FOR CONVERSION OF BIOLOGICALLY DERIVED MEVALONIC ACID

The invention relates to a process comprising reacting mevalonic acid, or a solution comprising mevalonic acid, to yield a first product or first product mixture, optionally in the presence of a solid catalyst and/or at elevated temperature and/or pressure. The invention further relates to a process comprising: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting said biobased mevalonic acid to yield a first product or first product mixture.

Reinvestigation of a Synthesis of (R,S)-Mevalonolactone

An n.m.r. study of the reaction of 3-hydroxy-3-methylpentane-1,5-dioic acid (5) with excess of acetic anhydride is described.It has shown that 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), previously described by Scott and Shishido as an intermediate in their synthesis of mevalonolactone, is formed only transiently, along with 3-acetoxy-3-methylpentane-1,5-dioic acid (6).Both intermediates eventually give 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).To obtain (R,S)-mevalonolactone, sodium borohydride reduction of 3-hydroxy-3-methylpentane-1,5-dioic acid anhydride (2), prepared from the diacid (5) and N,N-dicyclohexylcarbodi-imide, is shown to be better than reduction of 3-acetoxy-3-methylpentane-1,5-dioic acid anhydride (3).