[3aR-(3aalpha,4alpha,5beta,6aalpha)]-Hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one
[CAS# 81190-06-9]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: [3aR-(3aalpha,4alpha,5beta,6aalpha)]-Hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aR,4S,5R,6aS)-Hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.30
• CAS Registry Number: 81190-06-9
• SMILES: C1[C@H]2[C@H](CC(=O)O2)[C@H]([C@@H]1OCC3=CC=CC=C3)CO

Properties

• Solubility: Slightly soluble (1.6 g/L) (25 ºC), Calc.^*
• Density: 1.25±0.1 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.576, Calc.^*
• Boiling Point: 456.1±35.0 ºC (760 mmHg), Calc.^*
• Flash Point: 172.7±19.4 ºC, Calc.^*

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

Discovory and Applicatios

The chemical substance [3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one represents an intriguing compound within the realm of synthetic organic chemistry. This bicyclic structure has garnered interest for its potential applications in medicinal chemistry, primarily due to its unique molecular characteristics and possible therapeutic benefits.

The discovery of [3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one is rooted in ongoing efforts to explore and modify naturally occurring compounds for enhanced biological activity. Researchers have focused on the structural features of cyclopenta[b]furan derivatives, which are known for their diverse range of biological activities. The addition of hydroxymethyl and phenylmethoxy groups in this compound serves to improve its pharmacological profile, making it a candidate for further investigation.

The applications of [3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one extend primarily into the pharmaceutical sector, particularly in developing therapeutic agents for treating inflammatory and pain-related conditions. Preliminary studies suggest that this compound exhibits notable anti-inflammatory and analgesic properties, making it a potential candidate for addressing conditions such as arthritis, musculoskeletal pain, and other inflammatory disorders.

The presence of the hydroxymethyl group enhances the compound's solubility and bioavailability, which are crucial factors in pharmacokinetics. This structural modification allows for better interaction with biological targets, thereby improving therapeutic efficacy. The phenylmethoxy moiety contributes to the compound’s stability and provides a site for potential interactions with cellular receptors, further enhancing its activity profile.

Research is currently focused on the mechanism of action of this compound, with particular attention to how it interacts with specific pathways related to inflammation and pain. Understanding its pharmacodynamics will help elucidate the therapeutic window and guide dosage considerations in clinical settings.

Additionally, [3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one is also being explored for its potential in structure-activity relationship (SAR) studies. This involves modifying different parts of the molecule to assess changes in activity, providing valuable insights for the design of more effective analogs.

The ongoing research and development of [3aR-(3aalpha,4alpha,5beta,6aalpha)]-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one underline its significance in medicinal chemistry and drug discovery. Its unique structure and promising biological activity highlight the compound’s potential in contributing to new therapeutic strategies.