(3aalpha,4alpha,5beta,6aalpha)-(±)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
[CAS# 81244-64-6]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (3aalpha,4alpha,5beta,6aalpha)-(±)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Synonyms: [4-(hydroxymethyl)-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• Molecular Formula: C₁₅H₁₆O₅
• Molecular Weight: 276.29
• CAS Registry Number: 81244-64-6
• EC Number: 888-715-1
• SMILES: C1C2C(CC(=O)O2)C(C1OC(=O)C3=CC=CC=C3)CO

Properties

• Solubility: Very slightly soluble (0.94 g/L) (25 °C), Calc.^*
• Density: 1.33±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Discovery and Applications

(3aα,4α,5β,6aα)-(±)-5-(Benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one is a complex organic compound that has attracted attention due to its unique structural characteristics and potential applications in the fields of medicinal chemistry and material science. This compound belongs to a class of bicyclic lactones, which are known for their diverse biological activities and significance as synthetic intermediates.

The discovery of this compound can be linked to the growing interest in bicyclic structures within natural product chemistry. Bicyclic lactones, particularly those with hydroxymethyl and benzoyloxy substituents, are often found in various natural products with therapeutic properties. Researchers have synthesized derivatives of such compounds to explore their potential pharmacological effects and to develop new medicinal agents. The specific stereochemistry of (3aα,4α,5β,6aα)-(±)-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one plays a crucial role in determining its biological activity, making it an intriguing target for synthetic organic chemists.

The synthesis of this compound typically involves multiple steps, including the formation of the lactone ring and the introduction of functional groups such as the benzoyloxy and hydroxymethyl moieties. These synthetic strategies often require careful control of reaction conditions to ensure the desired stereochemistry is achieved, which is critical for the compound’s bioactivity.

In terms of applications, (3aα,4α,5β,6aα)-(±)-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one has shown potential in medicinal chemistry as a lead compound for the development of new pharmaceuticals. Preliminary studies suggest that derivatives of this compound may exhibit anti-inflammatory, antitumor, and antiviral properties, making them candidates for further investigation in drug development programs.

Moreover, the unique structural features of this bicyclic lactone lend themselves to applications in material science. The ability to modify the compound's structure opens avenues for creating novel materials with specific properties, such as improved mechanical strength, thermal stability, and biodegradability. Such materials can find uses in a variety of applications, including drug delivery systems, packaging, and coatings.

In conclusion, (3aα,4α,5β,6aα)-(±)-5-(benzoyloxy)hexahydro-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one is a significant compound in the realm of organic chemistry, with its discovery and potential applications highlighting the importance of bicyclic lactones in advancing medicinal and material sciences.

References

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