(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one
[CAS# 53872-60-9]

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-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one
• Synonyms: (3aR,4R,5R,6aS)-5-hydroxy-4-[(E,3R)-3-hydroxy-4-[3-(trifluoromethyl)phenoxy]but-1-enyl]-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
• Molecular Formula: C₁₈H₁₉F₃O₅
• Molecular Weight: 372.34
• CAS Registry Number: 53872-60-9
• EC Number: 805-964-3
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)/C=C/[C@H](COC3=CC=CC(=C3)C(F)(F)F)O)O

Safety Data

• Hazard Symbols: GHS07;GHS08 Warning
• Risk Statements: H315-H319-H335-H361-H362
• Safety Statements: P203-P260-P261-P263-P264-P264+P265-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P318-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Lact.	-	H362
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

(+)-(3aR,4R,5r,6aS)-Hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one is a complex organic compound notable for its unique bicyclic structure and potential applications in medicinal chemistry. The discovery of this compound is rooted in the exploration of structurally diverse bicyclic molecules, which has attracted significant attention due to their potential biological activity and utility in drug development.

The molecular architecture of (+)-(3aR,4R,5r,6aS)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one features a hexahydrocyclopentafuran moiety that contributes to its rigidity and defines its three-dimensional conformation. The presence of hydroxyl and trifluoromethyl groups introduces polarity and enhances the compound's potential interactions with biological targets. These structural characteristics are significant in determining the compound's reactivity and pharmacological properties.

This compound has garnered attention due to its possible applications in treating conditions related to ocular health. Its structural similarity to known ophthalmic agents suggests that it may act as a potent modulator of intraocular pressure, making it a candidate for the management of glaucoma. Research into the pharmacological properties of this compound indicates that it may exhibit prostaglandin-like effects, which could be beneficial in the treatment of ocular hypertension.

Furthermore, the presence of the trifluoromethyl group enhances the compound's lipophilicity, facilitating its absorption and distribution within biological systems. This characteristic is particularly advantageous in drug development, where optimizing pharmacokinetics is crucial for the efficacy of therapeutic agents. Studies have indicated that compounds with similar structural features can effectively penetrate biological membranes, allowing for targeted action in specific tissues, such as the eye.

The potential applications of (+)-(3aR,4R,5r,6aS)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one extend beyond ophthalmology. Its unique structure and reactivity also make it a valuable intermediate in the synthesis of other biologically active compounds. The compound can participate in various chemical transformations, including nucleophilic substitutions and functional group modifications, contributing to the development of new drugs with enhanced therapeutic profiles.

In summary, (+)-(3aR,4R,5r,6aS)-hexahydro-5-hydroxy-4-[(1E,3R)-3-hydroxy-4-(3-trifluoromethyl)phenoxy-1-butenyl]-2H-cyclopenta[b]furan-2-one is a promising compound in the field of medicinal chemistry, with potential applications in treating ocular diseases and serving as an intermediate for further synthetic development. Ongoing research is focused on elucidating its full pharmacological profile and exploring its utility in various therapeutic contexts, underscoring its significance in advancing drug discovery and development.

References

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