Oleuropein

Identification
Name
 

 
Oleuropein
Synonyms
 

 
Methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate; Olive Leaf Extract
Chinese Names
 

 
橄榄苦甙; 橄榄苦苷; 油橄榄叶提取物
Molecular Structure
 

 
Oleuropein, Methyl (4S,5E,6S)-4-[2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl]-5-ethylidene-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4H-pyran-3-carboxylate, Olive Leaf Extract CAS #: 32619-42-4
 

 
Molecular Formula
 

 
C25H32O13
Molecular Weight
 

 
540.51
CAS Registry Number
 

 
32619-42-4
EINECS
 

 
251-129-6
Properties
Minute crystals from ethyl acetate, mp 87-89° Hygroscopic. [alpha]D20 -147°(H2O, alcohol, or acetone). Shows mutarotation [alpha]D20 -127°after 9°hrs (H2O). Freely sol in acetone, ethanol, methanol, pyridine, glacial acetic acid, 5% a
Synthesis: Bitter principle of olives, Olea europaea, isol. also from Fraxina japonicus.
Physics Description: Cryst. (EtOAc).
Melting Point: Mp 89-91 deg
Partition Coefficient: Log P -1.75 (uncertain value) (calc).
Other Data: Artifact.

Use
Antihypertensive agent.

Synonym
Oleuropein

Reference
Shasha, B. et al.,J.O.C.,1961, 26, 1948 (isol) Panizzi, L. et al.,Gazz. Chim. Ital.,1965, 95, 1279 (isol) Asaka, Y. et al.,Chem. Lett.,1972, 141 (isol, struct) Inouye, H. et al.,Chem. Pharm. Bull.,1974, 22, 676 (biosynth) Inouye, H. et al.,Tetrahedron,1974, 30, 201 (abs config) Inouye, H. et al.,Phytochemistry,1975, 14, 304; ,2029; ,1982, 21, 2305 (isol, 10-Acetoxyoleuropein, 10-Acetoxyligustroside) Inouye, H. et al.,J. Chromatogr.,1976, 118, 201 (ms) Sutarjadi, M.T.M. et al.,Phytochemistry,1978, 17, 564 (Ligustroside) Kikuchi, M. et al.,CA,1985, 103, 147026 (isol, pmr, cmr) Shen, Y.-C. et al.,Phytochemistry,1990, 29, 2903; ,2905 (Multiroside, Ligustroside) Bianco, A. et al.,J. Nat. Prod.,1992, 55, 760 (synth) Damtoft, S. et al.,Phytochemistry,1992, 31, 4197; ,1993, 34, 1291; ,1995, 40, 785 (biosynth, Oleuropein, Ligustroside) Calis, I. et al.,Phytochemistry,1993, 33, 1453 (Angustifoliosides) Shen, Y.C. et al.,Planta Med.,1995, 61, 281 (Uhdenoside) Shen, Y.-C., J. Chin. Chem. Soc. (Peking),1996, 43, 171 (pmr, cmr) Tanahashi, T. et al.,Chem. Pharm. Bull.,1997, 45, 367 (4"-Glucopyranosyloleuropein) [00023532-9]

 

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