(3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one
[CAS# 62939-82-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₂H₁₆O₆
• Molecular Weight: 256.25
• CAS Registry Number: 62939-82-6
• SMILES: CC(=O)OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)OC(=O)C

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.27
• Index of Refraction: 1.497, Calc.^*
• Boiling Point: 384.6±27.0 °C (760 mmHg), Calc.^*
• Flash Point: 171.4±23.8 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

(3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one is a chemically intriguing compound belonging to the class of cyclopentanoid derivatives. This compound has garnered attention due to its potential biological activities and unique structural features, which include multiple functional groups that can engage in various biochemical interactions.

The discovery of (3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one was facilitated by a systematic exploration of cyclopentanoid frameworks, often derived from natural sources or synthesized through advanced organic chemistry techniques. Researchers aimed to create modified cyclopentanoids to investigate their pharmacological properties and therapeutic potentials. The acetyloxy and hydroxymethyl groups in this compound contribute significantly to its reactivity and biological interactions, enabling various synthetic pathways for modification and optimization.

The primary applications of (3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one lie in medicinal chemistry. Its structure suggests potential roles in anti-inflammatory and analgesic therapies, as compounds within this structural class often exhibit biological activity related to pain and inflammation modulation. The presence of acetyloxy groups may enhance the compound's solubility and bioavailability, critical factors in the development of therapeutic agents.

Recent studies have explored the compound’s interaction with specific biological targets, examining its efficacy in inhibiting pathways associated with inflammatory responses. The dual acetyloxy functionality not only enhances its pharmacokinetic properties but may also influence its affinity for receptors involved in pain signaling. These features make (3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one a compelling candidate for further development in the context of drug discovery.

Moreover, ongoing research aims to optimize this compound through structural modifications to enhance its pharmacological profile. By understanding the structure-activity relationship, scientists hope to design analogs with improved efficacy and selectivity for therapeutic applications, particularly in treating chronic inflammatory diseases.

The study of (3aR,4S,5R,6aS)-5-(Acetyloxy)-4-[(acetyloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-one exemplifies the innovative approaches in medicinal chemistry, where natural product-inspired structures are refined for therapeutic use. Continued investigation into its biological activities and mechanisms of action is expected to shed light on its potential as a new therapeutic agent in the pharmacopoeia.

References

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