(-)-Corey Lactone Benzoate Chemical Properties

Melting point:

116-120 °C

alpha 

-80 º (c=0.8, CHCl3 25 ºC)

Boiling point:

379.19°C (rough estimate)

Density 

1.2379 (rough estimate)

refractive index 

1.5000 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

pka

14.79±0.10(Predicted)

color 

White to Pale Yellow

InChI

InChI=1S/C15H16O5/c16-8-11-10-6-14(17)19-12(10)7-13(11)20-15(18)9-4-2-1-3-5-9/h1-5,10-13,16H,6-8H2/t10-,11-,12+,13-/m1/s1

InChIKey

OBRRYUZUDKVCOO-FVCCEPFGSA-N

SMILES

O1C(=O)C[C@]2([H])[C@@H](CO)[C@H](OC(=O)C3=CC=CC=C3)C[C@]12[H]

CAS DataBase Reference

39746-00-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

36/37/39-26

HS Code 

29321900

MSDS

• Language:English Provider:ACROS

(-)-Corey Lactone Benzoate Usage And Synthesis

Chemical Properties

Colorless crystalline powder

Uses

(-)-Corey Lactone Benzoate is a corey lactone derivative used in the preparation prostaglandin analogues for use as vasolidator as well as EP4 receptor agonists.

Synthesis

A 1:1 methanol:methylene chloride solution (40 mL) of (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-2H-cyclopenta[b]furan-2-one-4-carbaldehyde (1) (purchased from Cayman Chemical Company, Ann Arbor, MI) (3.5 g, 12.8 mmol) in a 1:1 methanol:dichloromethane solution (40 mL). After 25 min of reaction, the reaction was quenched by careful addition of saturated aqueous citric acid solution (60 mL). The mixture was extracted with ethyl acetate (3 × 40 mL) and the organic layers were combined and washed sequentially with water (2 × 80 mL) and saturated saline (2 × 80 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the target compound 2 (2.43 g, 69% yield).

References

[1] Patent: US6353000, 2002, B1. Location in patent: Page column 10
[2] Journal of Pharmacology and Experimental Therapeutics, 1999, vol. 290, # 3, p. 1278 - 1284
[3] Patent: US6353014, 2002, B1. Location in patent: Page column 18

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