(3aS,4R,5S,6aR)-(+)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
[CAS# 76704-05-7]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aS,4R,5S,6aR)-(+)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aS,4R,5S,6aR)-5-hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• CAS Registry Number: 76704-05-7
• 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 ° (c=1.4 in MeOH)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P280-P305+P351+P338

Discovery and Applications

(3aS,4R,5S,6aR)-(+)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one is a chemical compound that has garnered attention for its unique structural features and potential applications in various fields, particularly in medicinal chemistry. This compound belongs to a class of bicyclic lactones, which are known for their bioactive properties and versatility in organic synthesis.

The discovery of this compound is rooted in the exploration of natural products and the development of synthetic methodologies aimed at constructing complex molecular architectures. Researchers have been particularly interested in lactones due to their presence in numerous biologically active natural products, which often exhibit significant pharmacological activities. The specific stereochemistry of (3aS,4R,5S,6aR)-(+)-hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one enhances its potential interactions with biological targets, making it a compound of interest for drug discovery.

The synthesis of this lactone typically involves strategies such as cyclization reactions and functional group manipulations. The presence of hydroxyl groups at specific positions in the structure contributes to its reactivity and potential for further modifications, allowing for the creation of a variety of derivatives that may exhibit enhanced biological activities.

In terms of applications, this compound is being investigated for its therapeutic potential, particularly in the treatment of various diseases. Its structural features suggest that it may interact with specific biological pathways, providing a foundation for the development of new drugs. Preliminary studies have indicated that derivatives of this compound may possess anti-inflammatory, antitumor, and antimicrobial properties, making them suitable candidates for further exploration in pharmaceutical research.

Furthermore, the unique chemical structure of (3aS,4R,5S,6aR)-(+)-hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one may also find applications in materials science. The ability to modify the compound's structure can lead to the development of novel materials with specific properties, such as biodegradability or enhanced mechanical strength.

In summary, (3aS,4R,5S,6aR)-(+)-hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one is a noteworthy compound with potential applications in drug development and materials science. Its discovery and ongoing research into its biological activities highlight the significance of lactone derivatives in advancing medicinal chemistry and related fields.

References

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