Corey lactone
[CAS# 69222-61-3]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Lactone
• Name: Corey lactone
• Synonyms: (3aR,4S,5R,6aS)-Hexahydro-4-(hydroxymethyl)-5-[(tetrahydro-2H-pyran-2-yl)oxy]-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₃H₂₀O₅
• Molecular Weight: 256.29
• CAS Registry Number: 69222-61-3
• EC Number: 614-936-8
• SMILES: C1CCOC(C1)O[C@@H]2C[C@H]3[C@@H]([C@H]2CO)CC(=O)O3

Properties

• Density: 1.26

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovory and Applicatios

Corey lactone is a significant compound in organic chemistry, primarily recognized for its structural complexity and versatility in synthetic applications. The compound is named after the esteemed chemist Elias J. Corey, who made groundbreaking contributions to the field of organic synthesis, earning the Nobel Prize in Chemistry in 1990. The discovery of Corey lactones is rooted in the development of novel synthetic methodologies during the 1960s, which enabled chemists to construct intricate cyclic structures efficiently.

The synthesis of Corey lactone typically involves the cyclization of acyclic precursors, often employing strategies such as intramolecular esterification. This method allows for the formation of a lactone ring, characterized by the presence of a carbonyl group adjacent to an ether. Corey lactone derivatives can be synthesized through various routes, including the use of suitable protecting groups and functional group interconversions, making them adaptable for diverse applications.

One of the primary applications of Corey lactone is as a building block in the synthesis of biologically active compounds. The compound has been utilized as an intermediate in the preparation of numerous natural products and pharmaceuticals, owing to its unique reactivity and functionalization potential. For example, Corey lactones have been employed in the synthesis of steroidal compounds and alkaloids, which possess a wide range of pharmacological activities.

In addition to its applications in medicinal chemistry, Corey lactone has also found utility in materials science. Its unique chemical structure enables the design of novel polymeric materials with tailored properties. The lactone can be polymerized to create polyesters, which are of interest in various fields, including biodegradable plastics and drug delivery systems.

Corey lactone has garnered attention in the academic community, where researchers continue to explore its synthetic utility and potential applications. Ongoing studies focus on the modification of the lactone structure to enhance its biological activity and the development of new synthetic methodologies to access a broader range of derivatives.

In summary, Corey lactone stands out as a crucial compound in organic synthesis, attributed to its discovery by Elias J. Corey and its extensive applications in pharmaceuticals and materials science. Its versatility as a synthetic intermediate continues to inspire research and innovation in various chemical domains.