[3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(Benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
[CAS# 69793-37-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(Benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.28
• CAS Registry Number: 69793-37-9
• SMILES: c1ccc(cc1)C(=O)OC[C@H]2[C@@H](C[C@H]3[C@@H]2CC(=O)O3)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.310
• Index of Refraction: 1.575, Calc.^*
• Boiling Point: 478.6±25.0 ºC (760 mmHg), Calc.^*
• Flash Point: 181.8±16.7 ºC, Calc.^*

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

Discovory and Applicatios

The chemical substance [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one represents a significant milestone in the field of synthetic organic chemistry and medicinal chemistry, primarily due to its unique structural attributes and potential therapeutic applications. This compound, with its complex bicyclic framework, has attracted attention for its promising bioactive properties.

The discovery of this particular compound is embedded in the broader context of research aimed at synthesizing derivatives of naturally occurring compounds. The design of [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is inspired by bioactive natural products known for their medicinal benefits. Researchers sought to enhance the pharmacological profiles of these compounds by modifying their structures, leading to the synthesis of this novel compound.

One of the primary applications of [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one lies in its potential as a therapeutic agent. Preliminary studies suggest that this compound exhibits anti-inflammatory and analgesic properties, making it a candidate for addressing various conditions such as pain, arthritis, and other inflammatory diseases. The incorporation of the benzoyloxy group enhances its bioavailability and potency, allowing for improved interactions with biological targets.

Additionally, the unique hexahydro-2H-cyclopenta[b]furan moiety contributes to the compound's stability and solubility, important factors for pharmaceutical applications. This structural feature not only aids in biological activity but also serves as a valuable scaffold for further derivatization. The ability to modify the compound opens up avenues for creating a library of analogs, which can be screened for enhanced efficacy or reduced side effects.

Moreover, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one is also of interest in the context of structure-activity relationship (SAR) studies. By analyzing how structural modifications influence its biological activity, researchers can optimize the compound for specific therapeutic targets. This knowledge is essential for the rational design of more effective drug candidates.

Research continues to explore the pharmacokinetics and pharmacodynamics of this compound, focusing on its mechanism of action and potential for combination therapies. Understanding how it interacts with various biological systems will be crucial for determining its therapeutic window and safety profile in clinical applications.

Overall, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-4-[(benzoyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one exemplifies the innovation in modern chemistry aimed at discovering new pharmacologically active compounds. Its promising bioactivity and structural complexity underscore its potential role in drug development and the advancement of medicinal chemistry.