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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:54:48 UTC
Update Date2022-03-07 02:54:40 UTC
HMDB IDHMDB0035872
Secondary Accession Numbers
  • HMDB35872
Metabolite Identification
Common NameOleuropein
DescriptionOleuropein is found in fruits. Oleuropein is a bitter principle of olives. Nutriceutical with antioxidant properties.Oleuropein is a chemical compound found in olive leaf from the olive tree (and leaves of privet) together with other closely related compounds such as 10-hydroxyoleuropein, ligstroside, and 10-hydroxyligstroside. All these compounds are tyrosol esters of elenolic acid that are further hydroxylated and glycosylated. Oleuropein and its metabolite hydroxytyrosol have powerful antioxidant activity both in vivo and in vitro and give extra-virgin olive oil its bitter, pungent taste. Oleuropein preparations have been claimed to strengthen the immune system
Structure
Thumb
Synonyms
Chemical FormulaC25H32O13
Average Molecular Weight540.518
Monoisotopic Molecular Weight540.18429109
IUPAC Namemethyl (2S,3E,4S)-4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethylidene-2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate
Traditional Nameoleuropein
CAS Registry Number32619-42-4
SMILES
[H][C@]1(CC(=O)OCCC2=CC(O)=C(O)C=C2)\C(=C/C)[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C1C(=O)OC
InChI Identifier
InChI=1S/C25H32O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h3-5,8,11,14,18,20-22,24-28,30-32H,6-7,9-10H2,1-2H3/b13-3+/t14-,18+,20+,21-,22+,24-,25-/m0/s1
InChI KeyRFWGABANNQMHMZ-ZCHJGGQASA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentMelleolides and analogues
Alternative Parents
Substituents
  • Melleolide-skeleton
  • P-methoxybenzoic acid or derivatives
  • O-hydroxybenzoic acid ester
  • Salicylic acid or derivatives
  • Benzoate ester
  • 3-halobenzoic acid or derivatives
  • Methoxyphenol
  • Halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Methoxybenzene
  • M-cresol
  • Anisole
  • 4-chlorophenol
  • 4-halophenol
  • Phenoxy compound
  • Phenol ether
  • Chlorobenzene
  • Halobenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Toluene
  • Phenol
  • Benzenoid
  • Aryl chloride
  • Monocyclic benzene moiety
  • Aryl halide
  • Vinylogous acid
  • Tertiary alcohol
  • Cyclic alcohol
  • Carboxylic acid ester
  • Cyclobutanol
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Ether
  • Organohalogen compound
  • Organochloride
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aldehyde
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point89 - 91 °CNot Available
Boiling Point772.86 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1734 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.865 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00003093
Chemspider ID4444876
KEGG Compound IDNot Available
BioCyc IDCPD-17784
BiGG IDNot Available
Wikipedia LinkOleuropein
METLIN IDNot Available
PubChem Compound5281544
PDB IDNot Available
ChEBI ID7747
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1666971
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Medina E, Brenes M, Romero C, Garcia A, de Castro A: Main antimicrobial compounds in table olives. J Agric Food Chem. 2007 Nov 28;55(24):9817-23. Epub 2007 Oct 31. [PubMed:17970590 ]
  2. Jemai H, Bouaziz M, Fki I, El Feki A, Sayadi S: Hypolipidimic and antioxidant activities of oleuropein and its hydrolysis derivative-rich extracts from Chemlali olive leaves. Chem Biol Interact. 2008 Nov 25;176(2-3):88-98. doi: 10.1016/j.cbi.2008.08.014. Epub 2008 Sep 7. [PubMed:18823963 ]
  3. Zbidi H, Salido S, Altarejos J, Perez-Bonilla M, Bartegi A, Rosado JA, Salido GM: Olive tree wood phenolic compounds with human platelet antiaggregant properties. Blood Cells Mol Dis. 2009 May-Jun;42(3):279-85. doi: 10.1016/j.bcmd.2009.01.001. Epub 2009 Feb 4. [PubMed:19195914 ]
  4. Jemai H, El Feki A, Sayadi S: Antidiabetic and antioxidant effects of hydroxytyrosol and oleuropein from olive leaves in alloxan-diabetic rats. J Agric Food Chem. 2009 Oct 14;57(19):8798-804. doi: 10.1021/jf901280r. [PubMed:19725535 ]
  5. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  6. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  7. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  8. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  9. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.