Novel tocopherol compounds IV. 5-tocopherylacetic acid and its derivatives

Heterocycles

Volumn 43, Issue 4, 1996, Pages 787-798

  Rosenau, Thomas ^c   Habicher, Wolf Dieter ^a   Chen, Chen Loung ^b  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

^b NORTH CAROLINA STATE UNIVERSITY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001692487     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-95-7328     Document Type: Article

References (19)

1. T. Rosenau and W. D. Habicher, Tetrahedron, 1995, 51, 7919. T. Rosenau, C. L. Chen, and W. D. Habicher, J. Org. Chem., 1995, 60, 8120.
2. T. Rosenau and W. D. Habicher, Tetrahedron, 1995, 51, 7919. T. Rosenau, C. L. Chen, and W. D. Habicher, J. Org. Chem., 1995, 60, 8120.
3. 5-Tocopherylacetic acids and some of its derivatives show promising behavior with regard to the establishment of reversible redox systems, i.e., compounds that can be oxidized and re-reduced several times without loss in substance. This renders them particularly valuable as phase-transfer catalysts in oxidation reactions.
4. H. M. Fales, J. Chem. Soc., Perkin Trans. 2, 1990, 1005.
5. P. Schudel, H. Mayer, J. Metzger, R. Rüegg, and O. Isler, Helv. Chim. Acta, 1963, 46, 636.
6. Houben-Weyl 'Methoden der Organischen Chemie,' Vol. VI-3, G. Thieme, Stuttgart, 1965, pp. 56.
7. A. Pinner, 'Die Imidoaether und ihre Derivate,' Oppenheim, Berlin, 1892. For a review see: R. Roger and D. G. Neison, Chem. Rev., 1961, 61, 179.
8. A. Pinner, 'Die Imidoaether und ihre Derivate,' Oppenheim, Berlin, 1892. For a review see: R. Roger and D. G. Neison, Chem. Rev., 1961, 61, 179.
9. The ortho-quinonemethide of α-tocopherol formed by C-5a has been widely accepted as a commonly occurring intermediate in the chemistry of vitamin E: R. M. Parkhurst and W. A. Skinner, The Chemistry of Heterocyclic Compounds: Chromans and Tocopherols,' Vol. 37, ed. by G. P.Ellis and I. M. Lockhardt, John Wiley and Sons, Inc., New York, 1981. Analogously, the frequently observed occurrence of the ortho-quinonemethide in oxidation reactions of α-tocopherol or its model 2,2,5,7,8-pentamethylchroman-6-ol demonstrates that this intermediate is also favored in the case of oxidation reactions, and explains the huge number of products derived from this intermediate depending on the different oxidants and solvents applied: S. Suarna and P. T. Southwell-Keley, Lipids, 1989, 24, 56; S. Suarna and P. T Southwell-Keley, Lipids, 1989, 26, 187.
10. The ortho-quinonemethide of α-tocopherol formed by C-5a has been widely accepted as a commonly occurring intermediate in the chemistry of vitamin E: R. M. Parkhurst and W. A. Skinner, The Chemistry of Heterocyclic Compounds: Chromans and Tocopherols,' Vol. 37, ed. by G. P.Ellis and I. M. Lockhardt, John Wiley and Sons, Inc., New York, 1981. Analogously, the frequently observed occurrence of the ortho-quinonemethide in oxidation reactions of α-tocopherol or its model 2,2,5,7,8-pentamethylchroman-6-ol demonstrates that this intermediate is also favored in the case of oxidation reactions, and explains the huge number of products derived from this intermediate depending on the different oxidants and solvents applied: S. Suarna and P. T. Southwell-Keley, Lipids, 1989, 24, 56; S. Suarna and P. T Southwell-Keley, Lipids, 1989, 26, 187.
11. The ortho-quinonemethide of α-tocopherol formed by C-5a has been widely accepted as a commonly occurring intermediate in the chemistry of vitamin E: R. M. Parkhurst and W. A. Skinner, The Chemistry of Heterocyclic Compounds: Chromans and Tocopherols,' Vol. 37, ed. by G. P.Ellis and I. M. Lockhardt, John Wiley and Sons, Inc., New York, 1981. Analogously, the frequently observed occurrence of the ortho-quinonemethide in oxidation reactions of α-tocopherol or its model 2,2,5,7,8-pentamethylchroman-6-ol demonstrates that this intermediate is also favored in the case of oxidation reactions, and explains the huge number of products derived from this intermediate depending on the different oxidants and solvents applied: S. Suarna and P. T. Southwell-Keley, Lipids, 1989, 24, 56; S. Suarna and P. T Southwell-Keley, Lipids, 1989, 26, 187.
12. The products obtained strongly resemble the fragments observed in ms spectra of natural tocopherols. Compare: J. R. Trudell, S. D. Sample Woodgate, and K. Djerassi, Org. Mass Spectr., 1970, 3, 753; S. E. Scheppele, R. K. Mitchum, C. J. Rudolph, K. F. Kinneberg, and G. V. Odell, Lipids, 1971, 7, 297, and references cited therein.
13. The products obtained strongly resemble the fragments observed in ms spectra of natural tocopherols. Compare: J. R. Trudell, S. D. Sample Woodgate, and K. Djerassi, Org. Mass Spectr., 1970, 3, 753; S. E. Scheppele, R. K. Mitchum, C. J. Rudolph, K. F. Kinneberg, and G. V. Odell, Lipids, 1971, 7, 297, and references cited therein.
14. S. Urano and M. Matsuo, Chem. Pharm. Bull., 1980, 28, 1992; S. Brownstein and K. U. Ingold, J. Org. Chem., 1989, 54, 561.
15. S. Urano and M. Matsuo, Chem. Pharm. Bull., 1980, 28, 1992; S. Brownstein and K. U. Ingold, J. Org. Chem., 1989, 54, 561.
16. IUPAC-IUB Commission on Biochem. Nomenclature (CBN), Arch. Biochim. Biophys., 1974, 165, 1; IUPAC-IUB Nomenclature of Tocopherols, Eur. J. Biochim., 1982, 123, 473.
17. IUPAC-IUB Commission on Biochem. Nomenclature (CBN), Arch. Biochim. Biophys., 1974, 165, 1; IUPAC-IUB Nomenclature of Tocopherols, Eur. J. Biochim., 1982, 123, 473.
18. 10 before it was used as a solvent.
19. The use of HBr seems to be crucial. Lower yields were obtained, if HCl was applied instead of HBr. Apart from this, crystallization of the imidate hydrochlorides was considerably impeded as compared to the imidate hydrobromides.