(-)-Corey Lactone Diol, 98%

Name: (-)-Corey Lactone Diol, 98% | CAS 32233-40-2
Brand: J&K Scientific
Availability: InStock

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Vendor: J&K Scientific

Product Information

Product Name	(-)-Corey Lactone Diol
IUPAC Name	(3aR,4S,5R,6aS)-5-Hydroxy-4-(hydroxymethyl)-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
CAS Number	32233-40-2
Molecular Formula	C₈H₁₂O₄
Molecular Weight	172.18 g/mol
MDL Number	MFCD00075234
PubChem CID	2724453
Purity	≥98% (GC)
Appearance	White to off-white crystalline powder
Melting Point	115–119 °C
Boiling Point	406.6 °C at 760 mmHg
Specific Rotation	[α]²⁰/D = −39° (c = 1, MeOH)
Solubility	Soluble in DMSO (34 mg/mL), methanol, and chloroform
InChI Key	VYTZWRCSPHQSFX-GBNDHIKLSA-N
SMILES	OC[C@H][C@H](O)C[C@@H]2OC(=O)C[C@H]12
Storage	Room temperature, dry, and sealed. Recommended below 15 °C.
Synonyms	(-)-Corey Lactone; Corey Lactone Diol; L-Corey Lactone; (-)-Corey Diol; (3aR,4S,5R,6aS)-(-)-Hexahydro-5-hydroxy-4-(hydroxymethyl)-2H-cyclopenta[b]furan-2-one

Applications

Prostaglandin Drug Synthesis

(-)-Corey lactone diol is the most widely used starting material in the industrial synthesis of prostaglandin-based therapeutics, including:

Glaucoma medications — latanoprost, travoprost, bimatoprost, and tafluprost (prostaglandin F₂α analogs that reduce intraocular pressure)
Pulmonary hypertension therapies — beraprost and iloprost (prostacyclin analogs with vasodilatory and antiplatelet properties)
Reproductive health agents — misoprostol and carboprost (prostaglandin E₁ and F₂α analogs used in obstetrics and gastroenterology)
Antiviral agents — entecavir (a nucleoside analog for hepatitis B, whose formal synthesis uses the Corey lactone skeleton)

Asymmetric Synthesis and Medicinal Chemistry

Beyond the prostaglandin family, Corey lactone diol serves as a versatile chiral synthon for constructing enantiomerically pure cyclopentanoid natural products and their analogs. Its well-defined stereochemistry, functional group compatibility, and commercial availability in enantiopure form make it a preferred starting material in academic total synthesis and pharmaceutical process development.

Structure–Activity Relationship (SAR) Studies

Researchers employ Corey lactone diol to rapidly generate libraries of prostaglandin analogs with modified side chains, enabling systematic exploration of structure–activity relationships for anti-inflammatory, cardiovascular, and oncological targets.

Handling and Safety

Store in a tightly sealed container at room temperature (recommended below 15 °C) in a dry environment. Avoid exposure to moisture and strong oxidizing agents. Refer to the Safety Data Sheet (SDS) for detailed handling precautions.

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Quality Assurance

J&K Scientific is ISO 9001:2015 certified. Each batch of (-)-Corey lactone diol is tested for purity (GC), melting point, specific rotation, and spectral conformity (IR, ¹H NMR) before release. A Certificate of Analysis (COA) is available upon request.

Bulk and Custom Orders

Need larger quantities or custom specifications? J&K Scientific offers scale-up from grams to kilograms with competitive pricing and reliable supply.

Selected Literature

Corey, E. J.; Weinshenker, N. M.; Schaaf, T. K.; Huber, W. J. Am. Chem. Soc. 1969, 91, 5675–5677. (Seminal Corey lactone synthesis)
Umekubo, N.; Suga, Y.; Hayashi, Y. Chem. Sci. 2020, 11, 1205–1209. (One-pot enantioselective Corey lactone synthesis)
Achmatowicz, B. et al. Tetrahedron Lett. 1985, 26(45), 5597–5600. (BF₃-mediated prostaglandin approach from Corey lactone)