(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one
[CAS# 41639-74-1]

Identification

• Classification: Flavors and spices >> Synthetic spice >> Lactone and oxygen-containing heterocyclic compound >> Furan and pyran
• Name: (+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3S)-3-hydroxy-5-phenylpent-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• Molecular Formula: C₁₈H₂₂O₄
• Molecular Weight: 302.36
• CAS Registry Number: 41639-74-1
• EC Number: 689-776-5
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)/C=C/[C@H](CCC3=CC=CC=C3)O)O

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.640, Calc.^*
• Boiling Point: 509.2±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 185.6±23.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H361
• Safety Statements: P203-P264-P280-P302+P352-P318-P321-P332+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361

Discovery and Applications

(+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one is a notable chemical compound recognized for its structural complexity and potential applications in medicinal chemistry and organic synthesis. The discovery of this compound is rooted in the broader study of cyclopentafuran derivatives, which have gained attention for their bioactivity and versatility as synthetic intermediates.

The synthesis of this compound is typically achieved through multi-step processes that involve the construction of the cyclopentafuran core followed by selective functionalization of the hydroxyl groups. The stereochemical configuration of the molecule is critical, as it influences the biological activity and reactivity of the compound. Techniques such as asymmetric synthesis and chiral catalysis are often employed to ensure the correct stereochemistry is obtained, reflecting the compound's complex chiral nature.

One of the primary applications of (+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one lies in its potential use as a bioactive molecule in pharmaceutical research. The presence of multiple hydroxyl groups and the phenyl substituent suggest that this compound may exhibit significant interactions with biological targets, potentially leading to the development of new therapeutic agents. Studies have indicated that similar compounds in the cyclopentafuran class demonstrate various biological activities, including anti-inflammatory and anti-cancer properties.

Additionally, this compound serves as an important intermediate in the synthesis of more complex molecules. The hexahydro-2H-cyclopenta[b]furan-2-one structure can be utilized in various chemical reactions, such as nucleophilic substitutions and cycloadditions, making it a valuable building block for constructing diverse organic frameworks. Its structural motifs can lead to the development of novel materials with tailored properties, useful in fields such as materials science and nanotechnology.

The interest in this compound is further supported by ongoing research into its mechanisms of action and potential applications in drug design. By understanding the pharmacological profile and reactivity of (+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one, chemists aim to leverage its unique structural features for the synthesis of new compounds that may address unmet medical needs.

In conclusion, (+)-(3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-5-phenyl-1-pentenyl]-2H-cyclopenta[b]furan-2-one represents a significant compound in organic synthesis and medicinal chemistry. Its structural complexity and potential bioactivity make it a focus of ongoing research, with implications for the development of novel therapeutic agents and synthetic methodologies.

References

2003. Latanoprost. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-12-0013