(+/-)-Corey lactone diol
[CAS# 54423-47-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound
• Name: (+/-)-Corey lactone diol
• Synonyms: (3aR,4S,5R,6aS)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• CAS Registry Number: 54423-47-1
• EC Number: 608-721-8
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)CO)O

Properties

• Density: 1.365
• Melting point: 117-119 °C
• alpha: -44

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H312-H318-H332
• Safety Statements: P261,

Discovery and Applications

(+/-)-Corey lactone diol is a significant organic compound that has drawn attention in the fields of synthetic organic chemistry and medicinal chemistry. This compound is a derivative of the Corey lactone family, which encompasses various cyclic esters recognized for their diverse biological activities and structural versatility. The discovery of Corey lactones, including the diol form, is attributed to the innovative synthetic methodologies developed by the renowned chemist Elias J. Corey, whose work has greatly influenced the field of organic synthesis.

The synthesis of Corey lactones dates back to the 1960s, when Corey introduced a series of strategies for constructing these complex cyclic structures. His groundbreaking research enabled chemists to assemble intricate molecular architectures that are prevalent in many natural products. The development of (+/-)-Corey lactone diol involved expanding upon these synthetic methods, allowing for the introduction of hydroxyl groups into the lactone framework, resulting in a compound with unique chemical properties and potential reactivity.

The synthetic pathway to (+/-)-Corey lactone diol typically begins with the lactone precursor, which is subjected to reduction reactions to yield the diol. This transformation often requires careful control of reaction conditions to achieve the desired stereochemistry and to minimize the formation of by-products. The resultant diol features two hydroxyl groups, which not only enhance its solubility but also provide functional handles for further chemical modifications.

One of the primary applications of (+/-)-Corey lactone diol lies in its role as an intermediate in the synthesis of more complex organic molecules. The presence of hydroxyl groups enables it to participate in various reactions, such as esterifications or etherifications, facilitating the construction of diverse compounds with potential biological activities. Researchers have explored its utility in the development of pharmaceutical agents, particularly those aimed at treating cancer and other diseases.

Additionally, (+/-)-Corey lactone diol has been investigated for its potential applications in materials science. The hydroxyl functionality can be leveraged to create polymeric materials with tailored properties, such as improved thermal stability or enhanced mechanical strength. Its unique chemical structure also allows for the design of specialized coatings or adhesives, which may find use in industrial applications.

In summary, (+/-)-Corey lactone diol represents a valuable compound in organic chemistry, serving as a versatile building block for further synthetic endeavors. Its discovery, rooted in the pioneering work of Elias J. Corey, has paved the way for continued research and exploration of lactone derivatives in both medicinal and materials chemistry.

References

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