Reaktion #2122496

ord-eb31309ac947484988c8b15260c6a2a4

Reaktionsgleichung

CC(=O)[O-].[Na+]
sodium acetate
C/C=C1/[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1
oleuropein
C/C=C1/[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1
oleuropein
→
OCCCc1ccc(O)c(O)c1
Hydroxytyrosol
C/C=C1/[C@H](O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1
oleuropein aglycone

Edukte

CC(=O)[O-].[Na+]
sodium acetate
C/C=C1/[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1
oleuropein
C/C=C1/[C@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C(C(=O)OC)[C@H]1CC(=O)OCCc1ccc(O)c(O)c1
oleuropein

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeisolated from OLE
  2. 2
    Sonstigeat 37° C.
  3. 3
    Sonstigefor 1 hr
  4. 4
    Sonstigeto remove the glucose moiety

Vorschrift

Hydroxytyrosol was prepared from homogeneous oleuropein isolated from OLE. The procedure involves treatment of oleuropein with β-glycosidase (including but not limited to Sigma G4511) in 80 mM sodium acetate pH 5.0 using 1 Unit of enzyme/μmole of substrate at 37° C. for 1 hr to remove the glucose moiety and to yield oleuropein aglycone. The oleuropein aglycone was then be treated with esterase (including but not limited to Sigma E0887) in sodium phosphate buffer at pH 7.5 using 1 Unit of enzyme/μ mole of substrate at 25° C. for 1 hr to yield hydroxytyrosol and elonelic acid. The final products were resolved and quantitated by LC-MS as described above. Detection and quantification were performed at 280 and 320 nm for hydroxytyrosol at 0.698 min (m/z 153) and oleuropein aglycone at 2.087 min (m/z 377), while 240 nm was used for the detection of elenolic acid at 1.846 min (m/z 241).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08574635B2uspto-grants-2013_11