(3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
[CAS# 57930-46-8]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₀H₁₄O₅
• Molecular Weight: 214.22
• CAS Registry Number: 57930-46-8
• SMILES: CC(=O)OC[C@H]1[C@@H](C[C@H]2[C@@H]1CC(=O)O2)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.297
• Index of Refraction: 1.510, Calc.^*
• Boiling Point: 382.7±22.0 °C (760 mmHg), Calc.^*
• Flash Point: 152.8±15.8 °C, Calc.^*

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

Discovery and Applications

(3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one, a member of the cyclopentanoid family, has drawn attention in medicinal chemistry due to its structural complexity and potential biological activities. This compound is characterized by its unique bicyclic structure, which includes an acetyloxy group and a hydroxymethyl moiety, contributing to its reactivity and biological interactions.

The discovery of this compound emerged from studies focused on synthesizing and modifying cyclopentanoid structures, which are known for their diverse pharmacological properties. Researchers aimed to explore the synthetic pathways leading to this compound to assess its potential therapeutic applications. The synthesis typically involves the use of advanced organic chemistry techniques, including stereoselective reactions that enable the construction of its complex chiral framework.

In terms of application, (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one has shown promise in various biological assays, particularly those examining anti-inflammatory and analgesic activities. The presence of the hydroxyl group suggests the potential for hydrogen bonding interactions, which can enhance binding affinity to specific biological targets. This characteristic is essential for its exploration as a lead compound in drug development.

Research indicates that the compound's structure allows for the modulation of certain pathways related to pain and inflammation, making it a candidate for treating conditions such as arthritis and other inflammatory diseases. Furthermore, the acetyloxy group could enhance its pharmacokinetic properties, potentially improving its bioavailability and therapeutic efficacy.

Ongoing investigations are focused on elucidating the compound's mechanism of action and its interactions with biological receptors. These studies are critical for understanding how structural modifications can influence biological activity, guiding future synthesis and development of analogs with improved therapeutic profiles.

The exploration of (3aR,4S,5R,6aS)-4-[(Acetyloxy)methyl]hexahydro-5-hydroxy-2H-cyclopenta[b]furan-2-one exemplifies the significance of natural product-inspired synthetic compounds in drug discovery. With further research, this compound may pave the way for novel therapeutic agents targeting inflammatory disorders and contribute to the broader understanding of cyclopentanoid chemistry.

References

none