Stabilization and first direct spectroscopic evidence of the o-quinone methide derived from vitamin E

Org Lett. 2002 Nov 28;4(24):4285-8. doi: 10.1021/ol026917f.

Abstract

[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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Stability
  • Indolequinones*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Oxidation-Reduction
  • Quinones / chemical synthesis*
  • Quinones / chemistry*
  • Temperature
  • Vitamin E / chemistry*

Substances

  • Indolequinones
  • Indoles
  • Quinones
  • quinone methide
  • Vitamin E