13C nuclear magnetic resonance studies on .ALPHA.-tocopherol and its derivatives.

Shiro Urano, Yuji Hattori, Shinju Yamanoi, Mitsuyoshi Matsuo

Chemical and Pharmaceutical Bulletin · 1980 · 40 citations · 1 references

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Abstract

The 13C signal assignments of the aromatic carbon atoms in α-tocopherol were confirmed using [methyl-13C] α-tocopherol. The 13C-NMR spectra of α-tocopherol alkyl ethers and 5-alkyl-2, 5, 7, 8-tetramethyl-2-(4, 8, 12-trimethyltridecyl) chroman-6 (5H)-ones, which are formed in the radical scavenging reaction of α-tocopherol with alkylradicals, were recorded and examined. In α-tocopherol and its alkyl ethers, C-5 is more shielded than nearly equivalent C-7. The chemical shift difference seems to be consistent with the reactivity difference between these carbon atoms, which is known as the"Mills-Nixon effect."

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