Title: Oleuropein
CAS Registry Number: 32619-42-4
CAS Name: [2S-(2a,3E,4b)]-3-Ethylidene-2-(b-D-glucopyranosyloxy)-3,4-dihydro-5-(methoxycarbonyl)-2H-pyran-4-acetic acid 2-(3,4-dihydroxyphenyl)ethyl ester
Molecular Formula: C25H32O13
Molecular Weight: 540.51
Percent Composition: C 55.55%, H 5.97%, O 38.48%
Literature References: Bitter glucoside; first secoiridoid to be isolated. Isolation from olives and the leaves and bark of the olive tree, Olea europaea L., Oleaceae and structural studies: Panizzi et al., Gazz. Chim. Ital. 90, 1449 (1960); Beyerman et al., Bull. Soc. Chim. Fr. 1961, 1821; Shasha, Leibowitz, J. Org. Chem. 26, 1948 (1961). Isoln from the ripe fruits of Ligustrum lucidum and L. japonicum Thunb, Oleaceae: Inouye, Nishioka, Tetrahedron 28, 4231 (1972). Revised structure and stereochemistry: Inouye et al., Tetrahedron Lett. 1970, 2459. Pharmacology: Petkov, Manolov, Arzneim.-Forsch. 22, 1476 (1972). Partial synthesis: A. Bianco et al., J. Nat. Prod. 55, 760 (1992).
Properties: Minute crystals from ethyl acetate, mp 87-89°. Hygroscopic. [a]D20 -147° (H2O, alcohol, or acetone). Shows mutarotation [a]D20 -127° after 9 hrs (H2O). Freely sol in acetone, ethanol, methanol, pyridine, glacial acetic acid, 5% aq NaOH soln. Moderately sol in water, dioxane, butanol, ethyl acetate, butyl acetate. Practically insol in ether, petr ether, chloroform, benzene, carbon tetrachloride.
Melting point: mp 87-89°
Optical Rotation: [a]D20 -147° (H2O, alcohol, or acetone); [a]D20 -127° |