DL-Mevalonolactone
[CAS# 674-26-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Lactone compound
• Name: DL-Mevalonolactone
• Synonyms: DL-Mevalonic acid lactone; (4R)-4-Hydroxy-4-methyl-oxan-2-one; (+/-)-Tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one
• Molecular Formula: C₆H₁₀O₃
• Molecular Weight: 130.14
• CAS Registry Number: 674-26-0
• EC Number: 211-615-0
• SMILES: CC1(CCOC(=O)C1)O

Properties

• Melting point: 24-27 °C
• Flash point: 113 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

DL-Mevalonolactone, with the chemical formula C6H10O3, is an important organic compound that plays a significant role in biochemical research and industrial applications. It is a lactone derivative of mevalonic acid, a key intermediate in the biosynthesis of sterols and other isoprenoids. DL-Mevalonolactone is utilized for its chemical properties and its role in various synthetic pathways.

The discovery of DL-mevalonolactone is closely linked to the study of mevalonic acid metabolism. Mevalonic acid, discovered in the 1950s by the research of A. K. G. and J. M., is a critical intermediate in the mevalonate pathway, which is involved in the biosynthesis of cholesterol, steroid hormones, and other isoprenoids. The lactone form, DL-mevalonolactone, was subsequently identified as a useful derivative for various chemical transformations and studies. It was found to possess unique reactivity, making it a valuable compound in organic synthesis.

In the realm of organic chemistry, DL-mevalonolactone is used primarily as an intermediate in the synthesis of complex molecules. Its lactone structure allows for further functionalization and transformation, making it a versatile building block in the creation of various chemical compounds. It is particularly useful in the synthesis of isoprenoid derivatives and in studies related to cholesterol and steroid metabolism. By modifying the lactone structure, researchers can explore different chemical and biological properties.

DL-mevalonolactone also has applications in pharmaceutical research. It serves as a precursor in the synthesis of drugs and other biologically active molecules. Its role in the mevalonate pathway makes it a relevant compound for studying the mechanisms of cholesterol synthesis and its regulation. Furthermore, DL-mevalonolactone's ability to participate in various chemical reactions makes it useful in designing new therapeutic agents.

In summary, DL-mevalonolactone is a key compound in organic synthesis and pharmaceutical research due to its role as an intermediate in the mevalonate pathway. Its discovery and development have enabled advancements in the synthesis of complex molecules and the study of cholesterol metabolism, highlighting its importance in both chemical and biological sciences.

References

2023. p140Cap modulates the mevalonate pathway decreasing cell migration and enhancing drug sensitivity in breast cancer cells. Cell Death & Disease, 14(12).
DOI: 10.1038/s41419-023-06357-z

1980. Mevalonolactone derivatives as inhibitors of 3-hydroxy-3-methylglutaryl coenzyme A reductase. Chemical and Pharmaceutical Bulletin, 28(5).
DOI: 10.1248/cpb.28.1509

1962. Cholesterol synthesis in rat brain: Differential incorporation of mevalonolactone-2-C14 and potassium mevalonate-2-C14. Archives of Biochemistry and Biophysics, 99(3).
DOI: 10.1016/0003-9861(62)90302-8