Stabilization and first direct spectroscopic evidence of the o-quinone methide derived from vitamin E.
[reaction: see text] The o-quinone methide (2) derived from vitamin E (1) can be stabilized at low temperatures in a complex with the highly polar N-methylmorpholine-N-oxide (5). The lifetime of 2 can thus be prolonged from less than 10 s to several minutes. In the complex formed, 2 adopts a zwitterionic, aromatic structure with the exocyclic methylene group in perpendicular arrangement to the ring plane, stabilized by the negatively charged oxygen in 5.
Rosenau
Thomas
T
University of Agricultural Sciences, Institute of Chemistry, Muthgasse 18, A-1190 Vienna, Austria. trosenau@edv2.boku.ac.at
Potthast
Antje
A
Elder
Tom
T
Kosma
Paul
P
D004355:Drug Stability; D045563:Indolequinones; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011809:Quinones / Q000138:chemical synthesis* / Q000737:chemistry*; D013696:Temperature; D014810:Vitamin E / Q000737:chemistry*
D045563:Indolequinones; D007211:Indoles; D011809:Quinones; C068040:quinone methide; D014810:Vitamin E