Vitamins, 4. Vitamin E (Tocopherols, Tocotrienols)
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Vitamins, 4. Vitamin E (Tocopherols, Tocotrienols)
Vitamins, 4. Vitamin E (Tocopherols, Tocotrienols)
Vitamins
Kai-U. Baldenius
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorLinda von dem Bussche-Hünnefeld
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorEckhard Hilgemann
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorKai-U. Baldenius
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorLinda von dem Bussche-Hünnefeld
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorEckhard Hilgemann
BASF Aktiengesellschaft, Ludwigshafen, Germany
Search for more papers by this authorAbstract
The article contains sections titled:
1. |
Introduction |
2. |
History |
3. |
Physical Properties |
4. |
Chemical Properties |
5. |
Metabolism and Importance in the Organism |
6. |
Deficiency, Requirement, and Application |
7. |
Analysis and Standardization |
8. |
Occurrence |
9. |
Economic Aspects |
10. |
Biosynthesis |
11. |
Production |
11.1. |
Semisynthetic Vitamin E: Isolation from Plant Oils and Methylation |
11.2. |
Totally Synthetic Vitamin E: Industrial Synthesis |
11.3. |
Trimethylhydroquinone |
11.4. |
Phytol and Isophytol |
11.5. |
Stereoselective Syntheses of α-Tocopherol |
General References
- 1 O. Isler, G. Brubacher: Vitamine I, Georg Thieme Verlag, Stuttgart 1982, p. 126.
- 2 P. Schudel, H. Mayer, O. Isler, in W. H. Sebrell, R. S. Harris (eds.): The Vitamins, vol. V, Academic Press, New York 1972.
- 3 L. J. Machlin (ed.): Vitamin E–A Comprehensive Treatise, Marcel Dekker, New York 1980.
- 4 W. Friedrich: Handbuch der Vitamine, Urban & Schwarzenberg, München 1987, p. 151.
- 5 M. Mino et al. (eds.): Vitamin E, Jpn. Sci. Soc. Press, Tokyo; Karger, Basel 1993.
- 6 L. Packer, J. Fuchs (eds.): Vitamin E in Health and Disease, Marcel Dekker, New York 1993.
- 7 Vitamin E Research & Information Service: Vitamin E Fact Book, La Grange, Illinois 1994.
- 8 Kirk-Othmer, vol. 21, p. 574.
Specific References
- 9 H. M. Evans, K. S. Bishop, Science (Washington D.C.) 56 (1922) 650.
- 10 H. M. Evans, Proc. Natl. Acad. Sci. USA 11 (1925) 373.
- 11 A. M. Pappenheimer, M. Goetsch, J. Exp. Med. 53 (1931) 11.
- 12 M. Goetsch, A. M. Pappenheimer, J. Exp. Med. 54 (1931) 145.
- 13
J. Wadell,
H. Steenbock,
J. Biol. Chem.
80
(1928)
431.
10.1016/S0021-9258(18)83864-9 Google Scholar
- 14 H. M. Evans, O. H. Emerson, G. A. Emerson, J. Biol. Chem. 113 (1936) 319.
- 15 O. H. Emerson, G. A. Emerson, A. Mohammad, H. M. Evans, J. Biol. Chem. 122 (1937) 99.
- 16 Distillation Products, US 2 486 541, 1946 (J. G. Baxter et al.).
- 17 E. Fernholz, J. Am. Chem. Soc. 60 (1938) 700.
- 18 P. Karrer et al., Helv. Chim. Acta 21 (1938) 520.
- 19 J. Green, P. Mamalis, S. Marcinkiewicz, D. McHale, Chem. Ind. (London) 73 (1960) . D. McHale, J. Green et al., J. Chem. Soc. 1963, 784. J. F. Pennock et al., Biochem. Biophys. Res. Commun. 17 (1964) 542.
- 20 P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 2517.
- 21 J. W. Scott, F. T. Bizzarro, D. R. Parrish, G. Saucy, Helv. Chim. Acta 59 (1976) 290.
- 22 C. D. Robeson, J. Am. Chem. Soc. 65 (1943) 1660.
- 23 C. D. Robeson, J. Am. Chem. Soc. 64 (1942) 1487.
- 24 P. Schudel, H. Mayer, J. Metzger, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 333.
- 25 J. G. Baxter, C. D. Robeson, J. D. Taylor, R. W. Lehman, J. Am. Chem. Soc. 65 (1943) 918.
- 26 H. Mayer, P. Schudel, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 650.
- 27 P. W. R. Eggitt, F. W. Norris, J. Sci. Food. Agric. 6 (1955) 689.
- 28 J. Green et al., J. Chem. Soc. 1959, 3362.
- 29 H. Rosenkrantz, J. Biol. Chem. 173 (1948) 439.
- 30 H. Finegold, H. T. Slover, J. Org. Chem. 32 (1967) 2557.
- 31 K. Tsukida, M. Ito, F. Ikeda, J. Vitaminol. 18 (1972) 24.
- 32 H. Mayer et al., Helv. Chim. Acta 50 (1967) 1168.
- 33 S. E. Scheppele et al., Lipids 7 (1972) 297.
- 34 R. P. Evstigneva, E. I. Zakharova, Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 34 (1991) 3.
- 35 J. Kohar, C. Suarna, P. T. Southwell-Keely, Lipids 28 (1993) 1015. S. Matsumoto, Y. Iitaka, S.-I. Nakano, M. Matsuo, J. Chem. Soc., Perkin Trans. 1 1993, 2727. C. Martius, H. Eilingsfeld, Justus Liebigs Ann. Chem. 607 (1957) 159. P. Schudel, H. Mayer, R. Rüegg, O. Isler, Helv. Chim. Acta 46 (1963) 637.
- 36 G. W. Burton, K. U. Ingold, Acc. Chem. Res. 19 (1986) 194. M. Foti, K. U. Ingold, J. Lusztyk, J. Am. Chem. Soc. 116 (1994) 9440. S.-I. Nagaoka et al., J. Phys. Chem. 96 (1992) 2754, 8184. R. H. Bisby, A. W. Parker, J. Am. Chem. Soc. 117 (1995) 5664.
- 37 G. W. Burton, Proc. Nutr. Soc. 53 (1994) 251.
- 38 V. W. Bowry, K. U. Ingold, R. Stocker, Biochem. J. 288 (1992) 341. K. U. Ingold, V. W. Bowry, R. Stocker, C. Walling, Proc. Natl. Acad. Sci. USA 90 (1993) 45. V. W. Bowry, D. Mohr, J. Cleary, R. Stocker, J. Biol. Chem. 270 (1995) 5756.
- 39 W. A. Pryor et al., J. Org. Chem. 58 (1993) 3521. K.-H. Ha, O. Igarashi, J. Nutr. Sci. Vitaminol. 36 (1990) 411. G. W. Burton et al., J. Am. Chem. Soc. 107 (1985) 7053. G. W. Burton, K. U. Ingold, J. Am. Chem. Soc. 103 (1981) 6472. E. Niki et al., Bull. Chem. Soc. Jpn. 59 (1986) 497. J. Lehmann, H. T. Slover, Lipids 11 (1976) 853.
- 40 B. Halliwell, J. M. C. Gutteridge: Free Radicals in Biology and Medicine, Clarendon Press, Oxford 1987.
- 41 G. W. Burton, K. U. Ingold: “Vitamin E: Biochemistry and Health Implications,” Ann. N.Y. Acad. Sci. 570 (1988) 7.
- 42 H. J. Kayden, M. G. Traber, J. Lipid Res. 34 (1993) 343.
- 43 H. E. Gallo-Torres in L. J. Machlin in (3) p. 193.
- 44 F. Gey, P. Puska: “Vitamin E: Biochemistry and Health Implications,” Ann. N.Y. Acad. Sci. 570 (1988) 268.
- 45 M. K. Horwitt, Nutr. Rev. 38 (1980) 105.
- 46 J. R. Walton, L. Packer in [(3), p. 495].
- 47 R. S. Panush, J. C. Delafuente, World Rev. Nutr. Diet. 45 (1985) 97.
- 48 H. J. Kayden, Neurology 43 (1993) 2167.
- 49 A. Emmerie, C. Engel, Recl. Trav. Chim. Pays-Bas 57 (1938) 1351.
- 50 C. C. Tsen, Anal. Chem. 33 (1961) 849.
- 51 G. T. Vatassery, G. A. Martenson, Clin. Chem. (Winston Salem, N.C.) 18 (1972) 1475. S. L. Taylor, M. P. Lambden, A. L. Tappel, Lipids 11 (1976) 530.
- 52 W. Boguth, R. Repges, Int. Z. Vitaminforsch. 39 (1969) 289. F. Linow, J. Pohl, Nahrung 14 (1970) 269.
- 53 J. D. Desai in (3) p. 68. A. P. De Leenheer, W. E. Lambert et al. (eds.): Modern Chromatographic Analysis of the Vitamins, 2nd ed., Marcel Dekker, New York 1992.
- 54 T.-S. Shin, J. S. Godber, J. Am. Oil Chem. Soc. 70 (1993) 1289.
- 55 W. Schüep, R. Rettenmaier, Methods Enzymol. 234 (1994) 294.
- 56 N. Cohen et al., Helv. Chim. Acta 64 (1981) 1158.
- 57 W. Bremser, F. Vogel, Org. Magn. Reson. 14 (1980) 155.
- 58 M. Vecchi et al., Helv. Chim. Acta 73 (1990) 782. G. Riss et al., Methods Enzymol. 234 (1994) 302.
- 59 National Formulary 14 (1975) 758.
- 60 S. R. Ames, J. Nutr. 109 (1979) 2198.
- 61 H. Weiser, M. Vecchi, Int. J. Vitam. Nutr. Res. 52 (1982) 351.
- 62 S. R. Ames, M. J. Ludwig, D. R. Nelan, C. D. Robeson, Biochemistry 2 (1963) 188. H. Weiser, M. Vecchi, M. Schlachter, Int. J. Vitam. Nutr. Res. 56 (1986) 45.
- 63 J. Bruggemann, K. H. Niesar, C. Zentz, Int. Z. Vitaminforsch. 33 (1963) 180.
- 64 M. K. Horwitt, Am. J. Clin. Nutr. 8 (1960) 451.
- 65 M. L. Scott, I. D. Desai, J. Nutr. 83 (1964) 39.
- 66 L. J. Machlin, E. Gabriel, M. Brian, J. Nutr. 112 (1982) 1437.
- 67 E.-L. Syväoja et al., J. Am. Oil Chem. Soc. 63 (1986) 328.
- 68 J. Bauernfeind in (3) p. 99.
- 69 O. Isler, Experientia 33 (1977) 555.
- 70 W. Janiszowska, J. F. Pennock, Vitam. Horm. (N.Y.) 34 (1976) 77.
- 71 G. Thomas, O. R. Threlfall, Biochem. J. 142 (1974) 437.
- 72 H. D'Harlingue, B. Camara, J. Biol. Chem. 260 (1985) 15200. O. Dogbo, B. Camara, Biochim. Biophys. Acta 920 (1987) 140.
- 73 P. S. Marshall, S. R. Morris, D. R. Threlfall, Phytochemistry 24 (1985) 1705.
- 74 A. Stocker, A. Rüttimann, W.-D. Woggon, Helv. Chim. Acta 76 (1993) 1729.
- 75 A. Stocker et al., Helv. Chim. Acta 77 (1994) 1721.
- 76 A. R. Welburn, Phytochemistry 9 (1970) 743.
- 77 A. M. Gavin, J. Am. Oil Chem. Soc. 58 (1981) 175.
- 78 T. Rubel: Vitamin-E-Manufacture, Noyes Development Corp., Park Ridge, N.J. 1969.
- 79 Eastman Kodak, US 3 153 054, US 3 153 055, 1962.
- 80 Hoffmann-La Roche, EP 316 729, 1987 (C. Fizet). Eastman-Kodak, US 3 108 120, 1963.
- 81 Eastman-Kodak, GB 774 855, 1955. Refining, US 2 704 764, 1955. Nisshin Oil Mills, JP 57 144 281, 1981. Nisshin Flour Milling, US 4 454 329, 1980 (Y. Kai, Y. Takagi). S. K. Kim, J. S. Rhee, Korean. J. Food. Sci. Technol. 14 (1982) 174.
- 82 General Mills, US 3 418 335, 1966.
- 83 Henkel, US 4 148 810, 1976. A. Struve, R. Schuh, Fette Seifen Anstrichmittel 87 (1985) 103.
- 84 Nisshin Oil Mills, GB 2 145 418, 1983. Eastman-Kodak, US 2 843 610, 1955; US 3 335 154, 1963. Nisshin Oil Mills, JP 055 959, 1974.
- 85 Yoshihara Seiyu, JP 057 729, 1981. Henkel, EP 171 009, 1984 (S. M. Willing, R. R. Swanson). Distillation Products, US 2 349 275, 1941 (K. C. D. Hickman); US 2 454 692, 1946 (N. D. Embree, N. H. Kuhrt). Showa Denko, JP 60 048 981, 1983.
- 86 Hoffmann-La Roche, EP 610 742, 1993 (C. Fizet).
- 87 Eisai, US 3 122 565, 1960 (S. Kijima et al.); US 3 402 182, 1966 (S. Kijima, T. Nakamura). Nisshin Flour Milling, JP 60 109 586, 1983. Bidec Bioind Dev Center, US 5 190 618, 1988 (T. Kawada et al.).
- 88 General Mills, US 3 819 657, 1972 (N. S. Baldwin et al.); DE 2 351 272, 1972. Eastman-Kodak, US 4 239 691, 1979. Ajinomoto, JP 56 068 677 = JP-AS 86/48838, 1979 (D. R. Neler, C. H. Foster). Henkel, EP 178 400, 1984 (S. M. Willing).
- 89 Eastman Kodak, US 2 640 058, 1949 (L. Weisler).
- 90 BASF, EP 338 429, 1989 (P. Lechtken, U. Hörcher, B. Jessel).
- 91 Distillation Products, US 2 486 539, 1946 (L. Weisler); US 2 486 542, (L. Weisler, A.-J. Chechak, L. Weisler, A.-J. Chechak).
- 92 Vitamins Lim., US 2 992 235, 1957 (J. Green, S. Z. Marcinkiewicz).
- 93 Eastman Kodak, US 2 592 531, US 2 592 628 , US 2 592 629, US 2 592 630, 1949 (J. G. Baxter). Eastman Kodak, US 2 843 604, 1955 (O. D. Hawks).
- 94 Henkel, EP 159 018, 1984 (N. S. Baldwin et al.).
- 95 Hoffmann-La Roche, US 2 411 967, US 2 411 968, US 2 411 969, 1946 (P. Karrer et al.). Eastman Kodak, US 3 444 213, 1967 (D. R. Nelan); US 3 631 068, 1971. Diamond Shamrock, US 3 708 505, 1971 (S. B. Greenbaum, W. Hacke, H. Horn). Nisshin Flour Milling, DE 2 743 920, 1976 (Y. Yoshino, K. Kondo, S. Kawagoe). Sumitomo, JP 60 054 380, 1983, 1985; Chem. Abstr. 103 (1985), 123 731. Eisai, JP 60 072 881, 1983, 1985; Chem. Abstr. 103 (1985) 160 390. A. Skoda, B. Proksa, M. Majar, CS 254 402, 1983; Chem. Abstr. 111 (1989) 233 286. BASF, EP 100 471, 1982 (J. L. Finnan); DE 3 203 487, 1983 (B. Schulz, E. Renauer).
- 96 Hoffmann-La Roche, US 2 723 278, 1954 (J. D. Surmatis et al.); DE-OS 1 909 164, 1968 (W. Metlesics, P. A. Wehrli). P. A. Wehrli, R. I. Fryer, W. Metlesics, J. Org. Chem. 36 (1971) 2910.
- 97 Hoffmann-La Roche, US 3 789 086, 1974.
- 98 Hoffmann-La Roche, EP 012 824, 1978 (P. Fitton, R. Propper).
- 99 BASF, DE 4 208 477, 1992 (P. Grafen et al.).
- 100 BASF, DE 4 243 464, 1992 (R. Lowack et al.).
- 101 Eisai, US 3 459 774, 1964. Eastman Kodak, US 3 538 119, 1970.
- 102 Rhône-Poulenc, FR 2 602 772, 1986 (A. Beind, F. Sagi).
- 103 G. S. Chernikov, N. G. Baranova, U. M. Azizov, I. B. Afanas'er, Khim. Farm. Zh. 22 (1988) 1244.
- 104 BASF, DE 1 739 183, 1968 (L. Schuster, H. Pommer); DE 1 668 874, 1968 (A. Arnold, H. Pasedach, H. Pommer). Rhône-Poulenc, DE 2 450 908, 1974 (M. Jouffret).
- 105 Hoffmann-La Roche, DE 2 221 624, 1972 (W. Brenner); EP 35 635, 1980 (D. Bartoldus, B. Lohri). Kuraray, JP 55 072 136, 1978. Sun Refining, EP 070 665, 1981 (C. X. Hsu, J. F. Lyons); EP 107 427, 1982 (C. Y. Hsu, J. F. Lyons). BASF, EP 93 880, 1982 (F. Thoemel, W. Hoffmann); DE 4 029 198, 1990 (B. Bockstiegel et al.). Mitsubishi Gas, EP 127 888, 1983, EP 167 153, 1986 (T. Ishiki et al.). Eisai, EP 294 584, 1987 (N. Hirose et al.). Jpn. Agency of Ind. Science and Techn., EP 369 823, 1988 (K. Takehira et al.). M. Shimizu et al., Bull. Chem. Soc. Jpn. 65 (1992) 1522. CK Fine Chemicals, JP 087 993, 1989. British Petroleum, EP 175 574, 1984 (C. G. Griggs).
- 106 S. Fujibayashi, K. Nakayama, Y. Nishiyama, Y. Ishii, Chem. Lett. 1994, 1345. O. A. Kholdeeva, A. V. Golovin, R. I. Maksimovskaya, I. V. Kozhevnikov, J. Mol. Catal. 75 (1992) 235. H. Lissel, H. Jansen in de Wal, R. Neumann, Tetrahedron Lett. 33 (1992) 1795. M. Shimizu, H. Orita, T. Hayakawa, K. Takehira, Tetrahedron Lett. 30 (1989) 471. Jpn. Agency Ind. Sciences Techn., EP 338 666, 1988 (M. Shimizu et al.).
- 107 BASF, DE 1 940 386, 1969 (L. Schuster, R. Oster). Kuraray; DE 2 250 066, 1971 (T. Kawaguchi et al.); DE 2 309 051 ,1972 (K. Murakami, T. Yasui). Union Rheinische Braunkohlen Kraftstoff, DE 225 543, 1972 (H. Hoever, E. Biller). BASF, EP 152 842, 1984 (F. J. Broecker et al.). Mitsubishi Gas, EP 198 476, 1985 (T. Yui, A. Ito, T. Takata); EP 264 823, 1986 (T. Yui, A. Ito).
- 108 Hoffmann-La Roche, DE 2 415 930, 1974. Mitsubishi Gas, EP 419 045, 1989. V. Durgakumari, G. Sreekanth, S. Narayanan, Res. Chem. Intermed. 14 (1990) 223. Asahi, JP 06 116 189, 1992 (K. Sakai, H. Oohashi).
- 109 BASF, DE 1 793 037, 1968 (L. Arnold et al.). Hoffmann-La Roche, US 3 857 892, 1972 (P. A. Wehrli).
- 110 BASF, DE 1 668 874, 1968 (L. Arnold et al.). P. A. Wehrli, R. I. Fryer, F. Pigott, G. Silverman, J. Org. Chem. 37 (1972) 2340.
- 111 V. A. Bushmelev, T. A. Kondrat'eva, M. A. Lipkin, A. V. Kondrat'ev, Khim. Farm. Zh. 25 (1991) 65.
- 112 Teijin, DE 2 314 600, 1973. Y. Ichikawa et al., Ind. Eng. Chem. Prod. Res. Dev. 18 (1979) 373.
- 113 Rhône-Poulenc, US 4 612 401, 1986 (M. Constantini et al.). C. K. Fine Chemicals, JP 62 192 337, 1986 (D. Yoshida). Mitsubishi Gas, EP 84 158, 1986 (T. Tomita); JP 59 227 835, 1984; US 4 477 682, 1981 (T. Tomita et al.).
- 114 Teijin, DE 2 345 062, 1973 (Y. Ichikawa et al.). Kuraray, JP 62 263 136, 1986 (T. Kuwimoti, H. Tamai).
- 115 C. Mercier, P. Cabardes, Pure Appl. Chem. 66 (1994) 1509. C. Mercier, P. Chabardes, Chem. Ind. (Dekker) 62 (1995) 213.
- 116 Rhône-Poulenc, DE-OS 2 418 342, 1973 (D. Michelet).
- 117 Rhône-Poulenc, DE-OS 2 518 028, 1974 (M. Jouffret).
- 118 Rhône-Poulenc, US 4 247 720, 1975 (M. M. Baudouin, R. M. Perron). Eastman Kodak, DE-OS 2 149 159, 1970 (J. G. Thweatt, F. M. Rash). Y. A. Joe et al., Bull. Korean Chem. Soc. 12 (1991) 253.
- 119 G. Saucy, R. Marbet, Helv. Chim. Acta 50 (1967) 2091.
- 120 BASF, DE 1 068 696, 1955; DE 1 073 476, 1960 (H. Pasedach, M. Seefelder); US 4 310 705, 1979 (A. Nissen et al.). W. Hoffmann, H. Pasedach, H. Pommer, Justus Liebigs Ann. Chem. 729 (1969) 52. W. Hoffmann, Chem. Ztg. 97 (1973) 23. Hoffmann-La Roche, US 2 628 250, 1951; 2 638 484, 1952; 2 660 608, 1952; 2 795 617, 1957 (W. Kimel). M. F. Carroll, J. Chem. Soc. 1940, 704, 1266; J. Chem. Soc. 1941, 507.
- 121 G. Saucy, R. Marbet, Helv. Chim. Acta 50 (1967) 162; Angew. Chem. 72 (1960) 869.
- 122 K. Itoi in R. Noyori (ed.): Organic Synthesis in Japan, Past, Present, and Future, Tokyo Kagaku Dozin, Tokyo 1993, p. 165.
- 123 Rhône-Poulenc, EP 44 771, 1980 (D. Morel). Rhône-Poulenc, EP 441 708, 1991 (P. Chabardes, C. Mercier). D. Morcel, G. Mignani, Y. Colenille, Tetrahedron Lett. 26 (1985) 6337. C. Mercier, G. Mignani, M. Aufrand, G. Allmang, Tetrahedron Lett. 32 (1991) 1433.
- 124 C. Fuganti, P. Grasselli, J. Chem. Soc., Chem. Commun. 1982, 205; 1979, 995. N. Cohen et al., J. Org. Chem. 46 (1981) 2445. N. Cohen et al., J. Am. Chem. Soc. 101 (1979) 6710. K. Chan et al., J. Org. Chem. 43 (1978) 3435. K. Chan, G. Saucy, J. Org. Chem. 42 (1977) 3828. K. Chan et al., J. Org. Chem. 41 (1976) 3497. N. Cohen et al., J. Org. Chem. 41 (1976) 3505, 3512. H. Mayer et al., Helv. Chim. Acta 61 (1978) 837. H. Leuenberger et al., Helv. Chim. Acta 62 (1979) 455. M. Schmid, R. Barner, Helv. Chim. Acta 62 (1979) 464. R. Zell, Helv. Chim. Acta 62 (1979) 474. R. Barner, M. Schmid, Helv. Chim. Acta 62 (1979) 2384. J. W. Scott et al., Helv. Chim. Acta 59 (1976) 290. L. Crombie et al., J. Chem. Soc., Chem. Commun. 1978, 59. D. L. Coffen et al., Heterocycles 39 (1994) 527.
- 125 BASF, EP 1 217 73, 1984 (H. Ernst et al.); EP 122 426, 1983 (H. P. Gehrken et al.). BASF, EP 76 448, 1983 (H. Ernst et al.).
- 126 N. Cohen et al., Helv. Chim. Acta 64 (1981) 1158.
- 127 J. Hübscher, R. Barner, Helv. Chim. Acta 73 (1990) 1068.
- 128 K. Sato et al., J. Org. Chem. 52 (1987) 5497. S. Takano et al., Synlett 1990, 451. Hoffmann-La Roche, EP 392 389, 1989 (A. Knierzinger, M. Scalone). Hoffmann-La Roche, EP 183 042, 1984 (H. Imfeld).
- 129 Hoffmann-La Roche, WO 90/01554, 1988 (A. Stokker, W. D. Woggon). Hoffmann-La Roche, EP 531 639, 1991 (F. Grüninger et al.).
- 130 Hoffmann-La Roche, EP 104 376, 1982 (R. Schmid et al.); EP 257 411, 1987 (Heiser, Stoller). K. Takabe et al., Tetrahedron Lett. 26 (1985) 5153. R. Noyori et al., J. Am. Chem. Soc. 109 (1987) 1596.
Further Reading
- G. Ball: Vitamins, 2nd ed., Wiley, Hoboken 2010.
-
John H. Block:
Vitamins, Survey,
Kirk Othmer Encyclopedia of Chemical Technology,
5th ed., vol. 25,
p. 781–808,
John Wiley & Sons,
Hoboken, NJ,
2007,
online DOI: 10.1002/0471238961.1921182219031520.a01.pub2.
10.1002/0471238961.1921182219031520.a01.pub2 Google Scholar
- G. F. Combs: The Vitamins, 3rd ed., Academic Press, 2007.
-
M. F. Holick:
Vitamin D,
2nd ed.,
Humana,
London
2010.
10.1007/978-1-60327-303-9 Google Scholar
- G. W. A. Milne, M. Delander: Vitamin D Handbook, Wiley-Interscience, Hoboken 2008.
-
J. Zempleni,
R. B. Rucker,
J. W. Suttie,
D. B. McCormick:
Handbook of Vitamins,
4th ed.,
CRC Press,
Boca Raton, FL
2007.
10.1201/9781420005806 Google Scholar