(-)-Corey lactone diol
[CAS# 32233-40-2]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: (-)-Corey lactone diol
• Synonyms: (-)-6beta-Hydroxymethyl-7alpha-hydroxy-cis-2-oxabicyclo[3.3.0]octan-3-one; (3aR,4S,5R,6aS)-(-)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one
• Molecular Formula: C₈H₁₂O₄
• Molecular Weight: 172.18
• CAS Registry Number: 32233-40-2
• EC Number: 608-721-8
• SMILES: C1[C@H]([C@@H]([C@@H]2[C@H]1OC(=O)C2)CO)O

Properties

• Melting point: 117-119 °C
• alpha: -44 °

Safety Data

• Hazard Symbols: GHS02;GHS07 Danger
• Risk Statements: H302-H312-H318-H332
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P317-P302+P352-P304+P340-P305+P354+P338-P317-P321-P330-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

(-)-Corey lactone diol, also known as (–)-trans-2,3-epoxy-4-hydroxy-1-methylcyclopentane, was synthesized and characterized by Nobel Laureate E. J. Corey and his research team in the 1960s. The synthesis involved the selective epoxidation of specific cyclopentene derivatives followed by hydrolysis to produce the diol in optically pure form. This discovery marked a major advance in organic chemistry, demonstrating the utility of cyclic diols in the synthesis of complex molecules.

Chemically, (-)-Corey lactone diol has a cyclopentane ring structure with trans-epoxide and hydroxyl groups on adjacent carbon atoms. This structure confers unique stereochemistry and reactivity necessary for its synthetic applications. The compound is typically a white crystalline solid, soluble in polar solvents, stable under mild conditions, and amenable to a wide range of organic transformations.

(-)-Corey lactone diol is a valuable synthetic intermediate for the preparation of complex natural products and pharmaceutical compounds. Its versatile functional groups can be modified to enhance bioactivity, bioavailability, and therapeutic efficacy in drug discovery.

Due to its chirality, (-)-Corey lactone diol is used as a chiral building block in asymmetric synthesis. It helps create enantiomerically pure compounds, which is essential for drug synthesis to optimize pharmacological properties and reduce side effects.

The hydroxyl and epoxy groups of this compound help it function as a catalyst or ligand in organic reactions. It participates in stereoselective transformations and metal-catalyzed processes, improving reaction efficiency and selectivity in chemical manufacturing.

Ongoing research focuses on expanding the application of (-)-Corey lactone diol in the following areas: studying its potential as a scaffold for novel drug design and development, especially in anticancer, anti-inflammatory and antimicrobial agents; exploring its role in polymer chemistry, nanotechnology and material design, exploiting its structural features for functional material synthesis and applications; studying its interactions with biological targets and metabolic pathways to elucidate biochemical mechanisms and develop diagnostic tools and therapeutic interventions.

Studies on the safety and regulatory compliance of (-)-Corey lactone diol ensure its safe handling and use in industrial and research settings. Regulatory guidelines address environmental impact assessments, occupational health guidelines, and product stewardship to mitigate potential risks associated with their synthesis and application.

References

2020. Synthesis of the Corey Lactone and Latanoprost. Synfacts.
DOI: 10.1055/s-0040-1719513

2020. Pot-Economic Organocatalytic Asymmetric Synthesis of the Corey Lactone. Synfacts.
DOI: 10.1055/s-0040-1707620

2019. Organocatalytic Baeyer-Villiger Oxidation for the Synthesis of Prostaglandins. Synfacts.
DOI: 10.1055/s-0039-1689892