Latanoprost Lactone Diol
[CAS# 145667-75-0]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: Latanoprost Lactone Diol
• Synonyms: (3aR,4R,5R,6aS)-Hexahydro-5-hydroxy-4-[(3R)-3-hydroxy-5-phenylpentyl]-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.38
• CAS Registry Number: 145667-75-0
• EC Number: 689-784-9
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)CC[C@H](CCC3=CC=CC=C3)O)O

Properties

• Density: 1.202
• Melting point: 69-71 °C

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

Latanoprost lactone diol is a significant chemical intermediate in the synthesis of latanoprost, a widely used pharmaceutical for treating glaucoma and ocular hypertension. The discovery of latanoprost lactone diol is tied to the development of prostaglandin analogs, where scientists sought to create more effective treatments for reducing intraocular pressure. The chemical structure of latanoprost lactone diol incorporates a lactone ring and diol functionality, making it a versatile intermediate in synthetic pathways.

The synthesis of latanoprost lactone diol is generally achieved through multi-step organic reactions that involve selective oxidation and reduction processes. The lactone ring, in particular, is crucial in determining the molecule’s stereochemistry and overall reactivity. Its discovery came as part of the ongoing research into prostaglandin derivatives, which started gaining traction in the 1990s. Latanoprost lactone diol serves as a precursor in the final steps of latanoprost synthesis, providing the molecular framework necessary for its biological activity.

In terms of application, latanoprost lactone diol’s primary role is in pharmaceutical manufacturing, specifically as an intermediate in producing latanoprost. Latanoprost is a prostaglandin F2α analog that helps increase the outflow of aqueous humor from the eyes, thereby lowering intraocular pressure. As glaucoma treatments became more refined, latanoprost emerged as one of the most effective drugs due to its favorable side effect profile and potency. The development of latanoprost lactone diol was essential to this success, enabling the efficient production of latanoprost on a commercial scale.

Beyond its role in latanoprost synthesis, latanoprost lactone diol has also been investigated for its potential in creating other prostaglandin analogs. Its chemical structure allows for modifications that can lead to the creation of new drugs with improved therapeutic properties. The versatility of the lactone diol structure is important in medicinal chemistry, where small changes in molecular configuration can significantly impact drug efficacy and safety.

References

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