On the constitution of α-tocopherol
On the constitution of α-tocopherol
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DOI：
10.1021/ja01270a057
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发表时间：
1938-01-01
影响因子：
15
通讯作者：
Fernholz, E
中科院分区：
文献类型：
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作者：
Fernholz, E
当从C29 H50 O2中减去durohydroquinone（C10 H14 O2）时，仍有烃残基C19 H36。热裂解是一个相对平稳的反应，并以67%的产率分离出杜对苯二酚。还分离出烃，并且其具有预期的性质。它不与过苯甲酸反应，但加入了大约一个溴分子。这一结果似乎最好通过使α-生育酚具有杜洛氢醌（II）与醇的单醚结构来解释，由于缺少两个氢原子，该单醚必须含有一个异环。然而，随着对α-生育酚研究的进展，这一假设不得不被放弃。在讨论这些实验之前，必须提及同时出现在其他实验室的某些出版物。独立地，麦克阿瑟和Watson 4进行了非常相似的观察，当他们注意到在高温下用硒处理α-生育酚时形成杜醌。加拿大调查人员从他们的观察中得出结论，
When durohydroquinone, C10H14O2, is sub-tracted from C29H50O2 there remains a hydrocarbon residue C19H36. The thermal splitting is a comparatively smooth reaction and durohydroquinone was isolated in a yield of 67%. A hydrocarbon also was isolated and it had the expected properties. It did not react with per-benzoic acid, but added approximately one molecule of bromine. This result seemed to bebest explained by giving «-tocopherol the structure of a mono-ether of durohydroquinone (II) with an alcohol which on account of a deficit of two hy-drogen atoms would have to contain an isocyclic ring. This assumption had to be abandoned, however, as the investigation of «-tocopherol progressed.Before entering into a discussion of these ex-periments, mention must be made of certain publications which, in the meantime haveappeared from other laboratories. Independently, McArthur and Watson4 made a very similar observation, when they noted the formation of duroquinone when «-tocopherol was subjected to treatment with seleniumat high temperatures. The Canadian investigators have drawn conclu-sions from their observations which, in a very