Mevalonolactone

Base Information

• Chemical Name: Mevalonolactone
• CAS No.: 19115-49-2
• Molecular Formula: C6H10 O3
• Molecular Weight: 130.144
• Hs Code.: 29329990
• European Community (EC) Number: 433-160-9
• UNII: 661X270Z3L
• Nikkaji Number: J37.661B
• Wikidata: Q27136326
• Metabolomics Workbench ID: 123441
• ChEMBL ID: CHEMBL1401520
• Mol file: 19115-49-2.mol

Synonyms:mevalonic acid lactone;mevalonolactone;mevalonolactone, (+-)-isomer;mevalonolactone, (R)-isomer;mevalonolactone, (S)-isomer;mevalonolactone, 3-(14)C-labeled

Chemical Property of Mevalonolactone

Chemical Property:

• Vapor Pressure: 0.000662mmHg at 25°C
• Refractive Index: -21.5 ° (C=3, EtOH)
• Boiling Point: 274.9°C at 760 mmHg
• PKA: 13.57±0.20(Predicted)
• Flash Point: 110℃
• PSA: 46.53000
• Density: 1.189g/cm³
• LogP: 0.07440
• Storage Temp.: 2-8°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 132

Purity/Quality:

98% ^*data from raw suppliers

(R)-Mevalonolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCOC(=O)C1)O
• Isomeric SMILES: C[C@]1(CCOC(=O)C1)O
• General Description: (R)-BETA-HYDROXY-BETA-METHYL-DELTA-VALEROLACTONE, also known as (R)-mevalonolactone, is a chiral lactone derivative of mevalonic acid, which serves as a key intermediate in the biosynthesis of isoprenoids and steroids. (R)-BETA-HYDROXY-BETA-METHYL-DELTA-VALEROLACTONE was synthesized enantioselectively in this study via a multi-step route starting from (2S,3R)-epoxide derived from nerol, achieving high enantiomeric purity (>95% ee). The synthetic pathway involved protective group strategies, ozonolysis, oxidative elimination, and catalytic hydrogenation, ultimately yielding (R)-mevalonolactone. This synthesis has potential applications in developing analytical tools, such as radioimmunoassays, for quantifying mevalonic acid in biological systems.

Technology Process of Mevalonolactone

There total 2 articles about Mevalonolactone 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:

macrophorin D → macrophorin A + (R)-mevalonolactone (19115-49-2,503-48-0)

Guidance literature:

With borane; In tetrahydrofuran;

Reference yield:

→ gymnoprenol A (m=5, n=2) (86989-11-9) + gymnoprenol A (m=6, n=2) (86989-10-8) + C55H106O10 + (R)-mevalonolactone (19115-49-2,503-48-0)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 0 ℃; for 24h;

DOI:10.1016/0031-9422(92)80475-T

Reference yield: 57.0%

4-(Hydroxyethyl)-4-methyl-1,3-dioxane + (R)-mevalonolactone (19115-49-2,503-48-0) → meglutol (503-49-1)

Guidance literature:

With nitric acid;

Downstream raw materials:

(3R)-1-[(S)-1-phenylethyl]mevalonamide

(3R)-5-O-acetyl-1-<(S)-phenylethyl>-mevalonamide

(2S,4S,8S)-10-Benzyloxymethoxy-8-methoxymethoxy-8-methyl-dec-5-yne-2,4-diol

(2R,4S,8S)-10-Benzyloxymethoxy-8-methoxymethoxy-8-methyl-dec-5-yne-2,4-diol

Refernces

A synthesis of (R)-mevalonolactone

10.1016/S0040-4020(01)88311-3

The study details an enantioselective synthesis of (R)-mevalonolactone (1) starting from (2S,3R)-epoxide 2, which was prepared with >95% enantiomeric excess (ee) by asymmetric epoxidation of nerol. The primary hydroxyl group of epoxide 2 was protected by formation of ethoxyethyl ether 5, and subsequent reduction yielded 6. Conversion of 6 to its benzyl ether 7 was followed by ozonolysis to afford intermediate 8. To remove an additional carbon from 8, it was converted to phenylselenide 9, and oxidative elimination formed an alkene, which was cleaved by further oxidation to yield alkenol 11. Oxidation of 11 with pyridinium dichromate in DMF gave 12, and reductive ozonolysis of 12 afforded benzyl ether 13. Finally, removal of the benzyl group by catalytic hydrogen transfer yielded (R)-mevalonolactone (1). The study aimed to develop a synthetic pathway that could lead to both prospective haptens and (R)-mevalonolactone from a common intermediate, with potential applications in the development of a radioimmunoassay for measuring mevalonic acid concentration in biological media.