Vitamins, 4. Vitamin E (Tocopherols, Tocotrienols)
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Vitamins
Manfred Eggersdorfer, Geo Adam, Michael John, Wolfgang Hähnlein, Ludvik Labler, Kai-U. Baldenius, Linda von dem Bussche-Hünnefeld, Eckhard Hilgemann, Peter Hoppe, Rainer Stürmer, Fritz Weber, August Rüttimann, Gérard Moine, Hans-Peter Hohmann, Roland Kurth, Joachim Paust, Wolfgang Hähnlein, Horst Pauling, Bernd–Jürgen Weimann, Bruno Kaesler, Bernd Oster, Ulrich Fechtel, Klaus Kaiser, Bernd de Potzolli, Michael Casutt, Thomas Koppe, Michael Schwarz, Bernd-Jürgen Weimann, Urs Hengartner, Antoine de Saizieu, Christof Wehrli, René Blum,
Werner Bonrath, Adrian Wyss, Gilberto Litta, Kai-U. Baldenius,
Linda von dem Bussche-Hünnefeld,
Eckhard Hilgemann,
Peter Hoppe, Rainer Stürmer, Thomas Netscher,
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 authorWerner Bonrath, Adrian Wyss, Gilberto Litta, Kai-U. Baldenius,
Linda von dem Bussche-Hünnefeld,
Eckhard Hilgemann,
Peter Hoppe, Rainer Stürmer, Thomas Netscher,
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 authorFirst published: 16 July 2021
Abstract
The article contains sections titled:
| 1 | Introduction |
| 2 | Historical Aspects |
| 3 | Physical and Chemical Properties |
| 4 | Occurrence |
| 5 | Biosynthesis |
| 6 | Production |
| 6.1 | Vitamin E from Natural Sources (Isolation from Plant Oils and Methylation) |
| 6.2 | Totally Synthetic Vitamin E: Industrial Synthesis |
| 6.3 | Trimethylhydroquinone |
| 6.4 | Phytol and Isophytol |
| 6.5 | Stereoselective Syntheses of α-Tocopherol |
| 7 | Metabolism and Importance for the Organism |
| 8 | Deficiency, Requirement, and Application |
| 8.1 | Symptoms and Health Benefits in Humans |
| 8.2 | Deficiency Symptoms and Animal Nutrition |
| 9 | Analysis and Standardization |
| 10 | Economic Aspects |
| References |
General References
- 1Isler, O. and Brubacher, G. (1982) Die E-Vitamine, in Vitamine I, Einleitung, Fettlösliche Vitamine, Georg Thieme Verlag, Stuttgart, pp. 1, 126–28; Chapt. 3, 151.
- 2 W.H. Sebrell and R.S. Harris eds. (1972) Tocopherols, in The Vitamins, vol. V, Chapt. 16, Academic Press, New York, pp. 165–317.
- 3 L.J. Machlin ed. (1980) Vitamin E – A Comprehensive Treatise, Marcel Dekker, New York.
- 4Bässler, K.H. (1987) Fettlösliche Vitamine, in Vitamine, Steinkopf, Darmstadt, pp. 90–136. doi: 10.1007/978-3-642-72435-0_3.
10.1007/978‐3‐642‐72435‐0_3 Google Scholar
- 5 L. Packer and J. Fuchs eds. (1993) Vitamin E in Health and Disease, Marcel Dekker, New York.
- 6Block, J.H. (2017) Vitamins; Kirk Othmer Encyclopedia of Chemical Technology, J. Wiley & Sons, New York, Print ISBN: 9780471484943, Online ISBN: 9780471238966. doi: 10.1002/0471238961.1921182219031520.a01.
10.1002/0471238961.1921182219031520.a01 Google Scholar
- 7Scott, J.W. (2000) Vitamins, Survey; Kirk Othmer Encyclopedia of Chemical Technology, J. Wiley & Sons, New York, Print ISBN: 9780471484943, Online ISBN: 9780471238966. doi: 10.1002/0471238961.
10.1002/0471238961 Google Scholar
- 8Casani, R. (2000) Vitamin E; Kirk Othmer Encyclopedia of Chemical Technology, J. Wiley & Sons, New York, Print ISBN: 9780471484943, Online ISBN: 9780471238966. doi: 10.1002/0471238961.2209200103011901.a01.
10.1002/0471238961.2209200103011901.a01 Google Scholar
- 9 G. Litwack ed. (2007) Vitamin E, Series Vitamins and Hormones, vol. 76, Elsevier, Inc.
- 10Ball, G.F.M. (2006) Vitamins In Foods: Analysis, Bioavailability, and Stability, CRC Press, Boca Raton, FL.
Specific References
- 11 IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN) (1982) Eur. J. Biochem. 123, 473–475; Pure Appl. Chem. 54, 1507–1510.
- 12Müller-Mulot, W., Rohrer, G., Oesterhelt, G., et al. (1983) Fette, Seifen, Anstrichmittel 85, 66–72.
- 13Matsumoto, A., Takahashi, S., Nakano, K. and Kijima, S. (1995) J. Jpn. Oil Chem. Soc. (Yukagaku) 44, 593–597; Chem. Abstr. 123, 226445.
- 14Irías-Mata, A., Stuetz, W., Sus, N., et al. (2017) J. Agric. Food Chem. 65, 7476–7482.
- 15Müller, M., Kröpfl, A. and Vetter, W. (2020) Anal. Bioanal. Chem. 412, 795–802.
- 16Evans, H.M. and Bishop, K.S. (1922) Science (Washington D.C.) 56, 650–651.
- 17Evans, H.M. (1925) Proc. Natl. Acad. Sci. USA 11, 373–377.
- 18Pappenheimer, A.M. and Goettsch, M. (1931) J. Exp. Med. 53, 11–26, plus 3 addnl. pages.
- 19Pappenheimer, A.M. and Goettsch, M. (1931) J. Exp. Med. 53, 145–164, plus 3 addnl. pages.
10.1084/jem.53.1.11 Google Scholar
- 20Wadell, J., Steenbock, H. and Van Donk, E. (1928) J. Biol. Chem. 80, 431–442.
10.1016/S0021-9258(18)83864-9 Google Scholar
- 21Evans, H.M., Emerson, O.H. and Emerson, G.A. (1936) J. Biol. Chem. 113, 319–332.
- 22Emerson, O.H., Emerson, G.A., Mohammad, A. and Evans, H.M. (1937) J. Biol. Chem. 122, 99–107.
- 23Baxter, J.G., Stern, M.H. and Weisler, L. (1949) US 2 486 541 (Distillation Products, Inc.).
- 24Fernholz, E. (1938) J. Am. Chem. Soc. 60, 700–705.
- 25Karrer, P., Fritzsche, H., Ringier, B.H. and Salomon, H. (1938) Helv. Chim. Acta 21, 520–525.
- 26Green, J., Mamalis, P., Marcinkiewicz, S. and McHale, D. (1960) Chem. Ind. 73–74.
- 27McHale, D., Green, J., Marcinkiewicz, S., et al. (1963) J. Chem. Soc. 784–791.
- 28Pennock, J.F., Hemming, F.W. and Kerr, J.D. (1964) Biochem. Biophys. Res. Commun. 17, 542–548.
- 29Schudel, P., Mayer, H., Metzger, J., et al. (1963) Helv. Chim. Acta 46, 2517–2526.
- 30Mayer, H., Schudel, P., Rüegg, R. and Isler, O. (1963) Helv. Chim. Acta 46, 963–982.
- 31Scott, J.W., Bizzarro, F.T., Parrish, D.R. and Saucy, G. (1976) Helv. Chim. Acta 59, 290–306.
- 32Eggersdorfer, M., Laudert, D., Létinois, U., et al. (2012) Angew. Chem. Int. Ed. 51, 12960–12990.
- 33Robeson, C.D. (1943) J. Am. Chem. Soc. 65, 1660.
- 34Robeson, C.D. (1942) J. Am. Chem. Soc. 64, 1487.
- 35Schudel, P., Mayer, H., Metzger, J., et al. (1963) Helv. Chim. Acta 46, 333–343.
- 36Baxter, J.G., Robeson, C.D., Taylor, J.D. and Lehman, R.W. (1943) J. Am. Chem. Soc. 65, 918–924.
- 37Stern, M.H., Robeson, C.D., Weisler, L. and Baxter, J.G. (1947) J. Am. Chem. Soc. 69, 869–874.
- 38Schudel, P., Mayer, H. and Isler, O. (1972) Chapt. 16. Tocopherols, II. Chemistry, in The Vitamins, (eds. W.H. Sebrell and R.S. Harris), vol. V, Academic Press, New York, pp. 168–218.
- 39Mayer, H., Schudel, P., Rüegg, R. and Isler, O. (1963) Helv. Chim. Acta 46, 650–671.
- 40Cohen, N., Scott, C.G., Neukom, C., et al. (1981) Helv. Chim. Acta 64, 1158–1173.
- 41Robeson, C.D. and Nelan, D.R. (1962) J. Am. Chem. Soc. 84, 3196–3197.
- 42Mayer, H., Schudel, P., Rüegg, R. and Isler, O. (1962) Chimia 16, 367.
- 43Schudel, P., Mayer, H., Metzger, J., et al. (1963) Helv. Chim. Acta 46, 636–649.
- 44Schudel, P., Mayer, H., Rüegg, R. and Isler, O. (1962) Chimia 16, 368.
- 45Nelan, D.R. and Robeson, C.D. (1962) Nature 193, 477.
- 46Eggitt, P.W.R. and Norris, F.W. (1955) J. Sci. Food Agric. 6, 689–696.
- 47Finegold, H. and Slover, H.T. (1967) J. Org. Chem. 32, 2557–2561.
- 48Tsukida, K., Ito, M. and Ikeda, F. (1972) J. Vitaminol. 18, 24–28.
- 49Baker, J.K. and Myers, C.W. (1991) Pharm. Res. 8, 763–770.
- 50Ohnmacht, S., West, R., Simionescu, R. and Atkinson, J. (2008) Magn. Res. Chem. 46, 287–294.
- 51Green, J., McHale, D., Marcinkiewicz, S., et al. (1959) J. Chem. Soc. 3362–3373.
- 52Rosenkrantz, H. (1948) J. Biol. Chem. 173, 439–447.
- 53Mayer, H., Vetter, W., Metzger, J., et al. (1967) Helv. Chim. Acta 50, 1168–1178.
- 54Scheppele, S.E., Mitchum, R.K., Rudolph, C.J. Jr., et al. (1972) Lipids 7, 297–304.
- 55Evstigneva, R.P. and Zakharova, E.I. (1991) Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. 34, 3–26.
- 56Kohar, I., Suarna, C. and Southwell-Keely, P.T. (1993) Lipids 28, 1015–1120.
- 57Matsumoto, S., Iitaka, Y. and Nakano, S.-i. and Matsuo, M. (1993) J. Chem. Soc., Perkin Trans. 1, 2727–2735.
10.1039/p19930002727 Google Scholar
- 58Martius, C. and Eilingsfeld, H. (1957) Justus Liebigs Ann.Chem. 607, 159–168.
- 59Schudel, P., Mayer, H., Rüegg, R. and Isler, O. (1963) Helv. Chim. Acta 46, 637–649.
- 60Burton, G.W. and Ingold, K.U. (1986) Acc. Chem. Res. 19, 194–201.
- 61Foti, M., Ingold, K.U. and Lusztyk, J. (1994) J. Am. Chem. Soc. 116, 9440–9447.
- 62Nagaoka, S.-I., Kuranaka, A., Tsuboi, H., et al. (1992) J. Phys. Chem. 96, 2754–2761.
- 63Nagaoka, S.-I., Mukai, K., Itoh, T. and Katsumata, S. (1992) J. Phys. Chem. 96, 8184–8187.
- 64Bisby, R.H. and Parker, A.W. (1995) J. Am. Chem. Soc. 117, 5664–5670.
- 65Burton, G.W. (1994) Proc. Nutr. Soc. 53, 251–262.
- 66Bowry, V.W., Ingold, K.U. and Stocker, R. (1992) Biochem. J. 288, 341–344.
- 67Ingold, K.U., Bowry, V.W., Stocker, R. and Walling, C. (1993) Proc. Natl. Acad. Sci. USA 90, 45–49.
- 68Bowry, V.W., Mohr, D., Cleary, J. and Stocker, R. (1995) J. Biol. Chem. 270, 5756–5763.
- 69Pryor, W.A., Cornicelli, J.A., Devall, L.J., et al. (1993) J. Org. Chem. 58, 3521–3532.
- 70Ha, K.-H. and Igarashi, O. (1990) J. Nutr. Sci. Vitaminol. 36, 411–421.
- 71Burton, G.W., Doba, T., Gabe, E.J., et al. (1985) J. Am. Chem. Soc. 107, 7053–7065.
- 72Burton, G.W. and Ingold, K.U. (1981) J. Am. Chem. Soc. 103, 6472–6477.
- 73Niki, E., Tsuchiya, J., Yoshikawa, Y., et al. (1986) Bull. Chem. Soc. Jpn. 59, 497–501.
- 74Lehmann, J. and Slover, H.T. (1976) Lipids 11, 853–857.
- 75Syväoja, E.-L., Piironen, V., Varo, P., et al. (1986) J. Am. Oil Chem. Soc. 63, 328–329.
- 76Slover, H.T. (1971) Lipids 6, 291–296.
- 77Piironen, V., Syväoja, E.-L., Varo, P., et al. (1986) J. Agric. Food Chem. 34, 742–746.
- 78Puah, C.W., Choo, Y.M., Ma, A.N. and Chuah, C.H. (2007) Am. J. Appl. Sci. 4, 374–377.
- 79Sheppard, A.J., Weihrauch, J.L. and Pennington, J.A.T. (1993) Chapt. I. Natural Occurrence and Tissue Levels, A. Plants, 2. Analysis and Distribution of Vitamin E in Vegetable Oils and Foods, in Vitamin E in Health and Disease, (eds. L. Packer and J. Fuchs), Marcel Dekker, pp. 9–32, New York.
- 80McLaughlin, P.J. and Weihrauch, J.L. (1979) J. Am Diet. Assoc. 75, 647–665.
- 81Ball, G.F.M. (2006) Chapt. 5.3.1 Occurrence, in Vitamins In Foods: Analysis, Bioavailability, and Stability, CRC Press, Boca Raton, FL, pp. 123–126.
- 82Taylor, P. and Barnes, P. (1981) Chem. Ind. 722–726.
- 83Bauernfeind, J. (1980) Chapt. 4, Tocopherols in Foods, in Vitamin E – A Comprehensive Treatise, (ed. L.J. Machlin), Marcel Dekker, New York, pp. 99–167.
- 84Hogarty, C.J., Ang, C. and Eitenmiller, R.R. (1989) J. Food Compos. Anal. 2, 200–209.
- 85Isler, O. (1977) Experientia 33, 555–573.
- 86Threlfall, D.R. (1971) Vitam. Horm. 29, 153–200.
- 87Janiszowska, W. and Pennock, J.F. (1976) Vitam. Horm. 34, 77–105.
- 88Thomas, G. and Threlfall, D.R. (1974) Biochem. J. 142, 437–440.
- 89d'Harlingue, H. and Camara, B. (1985) J. Biol. Chem. 260, 15200–15203.
- 90Dogbo, O. and Camara, B. (1987) Biochim. Biophys. Acta 920, 140–148.
- 91Porfirova, S., Bergmüller, E., Tropf, S., et al. (2002) Proc. Natl. Acad. Sci. USA 99, 12495–12500.
- 92Shigeoka, S., Ishiko, H., Nakano, Y. and Mitsunaga, T. (1992) Biochim. Biophys. Acta 1128, 220–226.
- 93Marshall, P.S., Morris, S.R. and Threlfall, D.R. (1985) Phytochemistry 24, 1705–1711.
- 94Sen, C.K., Khanna, S., Rink, C. and Roy, S. (2007) Vitam. Horm. 76, 203–261.
- 95Stocker, A., Rüttimann, A. and Woggon, W.-D. (1993) Helv. Chim. Acta 76, 1729–1738.
- 96Stocker, A., Netscher, T., Rüttimann, A., et al. (1994) Helv. Chim. Acta 77, 1721–1737.
- 97Wellburn, A.R. (1970) Phytochemistry 9, 743–748.
- 98DellaPenna, D. (2005) J. Plant Physiol. 162, 729–737.
- 99Yang, W., Cahoon, R.E., Hunter, S.C., et al. (2011) Plant J. 65, 206–217.
- 100Lushchak, V.I. and Semchuk, N.M. (2012) Acta Physiol. Plant 34, 1607–1628.
- 101Muñoz, P. and Munné-Bosch, S. (2019) Trends Plant Sci. 24, 1040–1051.
- 102Nagegowda, D.A. and Gupta, P. (2020) Plant Sci. 294, 110457.
- 103Pellaud, S., Bory, A., Chabert, V., et al. (2018) New Phytol. 217, 245–260.
- 104Kobayashi, N. and DellaPenna, D. (2008) Plant J. 55, 607–618.
- 105Shintani, D. and DellaPenna, D. (1998) Science 282, 2098–2100.
- 106Van Eenennaam, A.L., Lincoln, K., Durrett, T.P., et al. (2003) Plant Cell 15, 3007–3019.
- 107Woggon, W.-D. (1999) Angew. Chem. Int. Ed. 38, 2715–2716.
10.1002/(SICI)1521-3773(19990917)38:18<2715::AID-ANIE2715>3.0.CO;2-K CAS PubMed Web of Science® Google Scholar
- 108Gavin, A.M. (1981) J. Am. Oil Chem. Soc. 58, 175–184.
- 109Rubel, T. (1969) Vitamin E Manufacture, Chem. Proc. Rev. No. 39, Noyes Development Corp., Park Ridge, NJ.
- 110(a) Brown, W. (1964) US 3 153 054 (Eastman Kodak); (b) Brown, W. and Smith, F.E. (1964) US 3 153 055 (Eastman Kodak).
- 111(a) Fizet, C. (1989) EP 316 729 (F. Hoffmann-La Roche AG); (b) Brown, W. and Meng, K.H. (1963) US 3 108 120 (Eastman-Kodak).
- 112(a) Eastman Kodak, (1957) GB 774 855; (b) Mattikow, M. and Perlman, D. (1955) US 2 704 764 (Refining); (c) Takagi, Y., Yamagami, K. and Kuwabara, M. (1982) JP 57 144 281 (Nisshin Oil Mills); Chem. Abstr. (1983) 98, 89081; (d) Takagi, Y. and Kai, Y. (1980) US 4454329 (Nisshin Oil Mills).
- 113Kim, S.K. and Rhee, J.S. (1982) Korean J. Food Sci. Technol. 14, 174–178.
- 114Nakanishi, S. (1968) US 3 418 335 (General Mills).
- 115Struve, A. (1979) US 4 148 810 (Henkel Kommanditgesellschaft).
- 116Struve, A. and Schuh, R. (1985) Fette, Seifen, Anstrichmittel 87, 103–106.
- 117(a) Uchida, M., Takagi, Y., Maeda, K., et al. (1985) GB 2 145 418 (Nisshin Oil Mills); (b) Brown, W. and Rawlings, H.W. (1958) US 2 843 610 (Eastman Kodak Co.); (c) Smith, F.E. (1967) US 3 335 154 (Eastman Kodak Co.).
- 118(a) Willing, S.M. and Swanson, R.R. (1986) EP 171 009 (Henkel Corp.); (b) Hickman, K.C.D. (1944) US 2 349 275 (Distillation Products); (c) Embree, N.D. and Kuhrt, N.H. (1948) US 2 454 692 (Distillation Products); (d) Onodera, S. and Kiyono, M. (1985) JP 60 048 981 (Showa Denko KK).
- 119Fizet, C. (1993) EP 610 742 (F. Hoffmann-La Roche AG).
- 120(a) Kijima, S., Naito, K. and Mori, T. (1964) US 3 122 565 (Eisai Co.); (b) Kijima, S. and Nakamura, T. (1968) US 3 402 182 (Eisai Co.); (c) Toyoda, H. and Yuge, H. (1985) JP 60 109 586 (Nisshin Flour Milling Co.); (d) Top, A.G.M., Leong, L.W., Ong, A.S.H., et al. (1993) US 51 90 618 (Bidec, Palm Oil Board Malaysia).
- 121(a) Baldwin, W.S. and Keeney, K.W. (1974) US 3 819 657 (General Mills Chemicals); (b) Baldwin, W.S. and Keeney, K.W. (1974) DE 2 351 272 (General Mills Chemicals); (c) Nelan, D.R. and Foster, C.H. (1980) US 4 239 691 (Eastman Kodak Co.); (d) Eguchi, A., Kakizaki, F. and Saitou, H. (1981) JP 56 068 677 (Ajinomoto Co.); (e) Willing, S.M. (1986) EP 178 400 (Henkel Corp.).
- 122Brüggemann, K., Herguijuela, J.R. and Netscher, T. (1997) EP 0 769 497 (F. Hoffmann-La Roche AG).
- 123Weisler, L. (1953) US 2 640 058 (Eastman Kodak Co.).
- 124Lechtken, P., Hoercher, U. and Jessel, B. (1989) EP 338 429 (BASF Aktiengesellschaft).
- 125(a) Weisler, L. (1949) US 2 486 539 (Distillation Products); (b) Weisler, L. and Chechak, A.J. (1949) US 2 486 542 (Distillation Products).
- 126Green, J. and Marcinkiewicz, S.Z. (1961) US 2 992 235 (Vitamins Limited).
- 127(a) Baxter, J.G. (1952) US 2 592 531 (Eastman Kodak Co.); (b) Weisler, L. (1952) US 2 592 628 (Eastman Kodak Co.); (c) Weisler, L. (1952) US 2 592 629 (Eastman Kodak Co.); (d) Weisler, L. (1952) US 2 592 630 (Eastman Kodak Co.); (e) Hawks, O.D. (1958) US 2 843 604 (Eastman Kodak Co.).
- 128Baldwin, W.S., Willging, S.M. and Siegel, B.M. (1985) EP 159 018 (Henkel Corp.).
- 129Müller, R.K. and Schneider, H. (1996) EP 0 735 033 (F. Hoffmann-La Roche AG).
- 130Bonrath, W. and Netscher, T. (2005) Appl. Catal. A: Gen. 280, 55–73.
- 131(a) Karrer, P. and Isler, O. (1946) US 2 411 967, US 2 411 968, US 2 411 969 (Hoffmann-La Roche Inc.); (b) Nelan, D.R. (1969) US 3 444 213 (Eastman Kodak Co.); (c) Nelan, D.R. (1971) US 3 631 068 (Eastman Kodak Co.); (d) Greenbaum, S.B., Hacke, W. and Horn, H. (1973) US 3 708 505 (Diamond Shamrock Corp.); (e) Yoshino, Y., Kondo, K. and Kawagoe, S. (1978) DE 2 743 920 (Nisshin Flour Milling Co.); (f) Iwasa, M., Matsuda, T., Nishizaki, T. and Shimizu, S. (1985) JP 60 054 380 (Sumitomo Chemical Co.); Chem. Abstr. 103 (1985) 123731; (g) Banba, T., Seki, C., Takahashi, T. and Yokoyama, T. (1985) JP 60 072 881 (Eisai Co. Ltd.); Chem. Abstr. 103 (1985) 160390; (h) Finnan, J.L. (1984) EP 100 471 (BASF Aktiengesellschaft); (i) Schulz, B. and Renauer, E. (1983) DE 3 203 487 (BASF AG).
- 132Krill, S., Kretz, S. and Huthmacher, K. (2001) EP 1 132 384 (Degussa AG).
- 133(a) Surmatis, J.D. and Weber, J. (1955) US 2 723 278 (Hoffmann-La Roche Inc.); (b), Metlesics, W. and Wehrli, P.A. (1969) DE 1 909 164 (F. Hoffmann-La Roche & Co. AG).
- 134Wehrli, P.A., Fryer, R.I. and Metlesics, W. (1971) J. Org. Chem. 36, 2910–2912.
- 135Frick, H., Halder, N. and Vogler, W. (1974) US 3 789 086 (Hoffmann-La Roche Inc.).
- 136Fitton, P. and Propper, R. (1980) EP 012 824 (F. Hoffmann-La Roche & Co. Aktiengesellschaft).
- 137Grafen, P., Kiefer, H. and Jädicke, H. (1993) DE 4 208 477 (BASF AG).
- 138Lowack, R., Meyer, J., Eggersdorfer, M. and Grafen, P. (1994) DE 4 243 464, EP 0603695 (BASF AG).
- 139Matsui, M., Karibe, N., Hayashi, K. and Yamamoto, H. (1995) Bull. Chem. Soc. Jpn. 68, 3569–3571.
- 140Matsui, M. (1996) Nihon Yukagakkaishi, J. Jpn. Oil Chem. Soc. 45, 821–831; Chem. Abstr. 125, 301241.
- 141Baak, M., Bonrath, W. and Kreienbuehl, P. (1999) EP 949 255 (F. Hoffmann-La Roche AG).
- 142Baak, M., Bonrath, W. and Pauling, H. (1998), WO 9 821 197 (F. Hoffmann-La Roche AG).
- 143Bonrath, W., Haas, A., Hoppmann, E., et al. (2002) Adv. Synth. Catal. 344, 37–39.
- 144Bonrath, W., Aquino, F., Haas, A., et al. (2009) Sustainability 1, 161–168.
- 145(a) Nakamura, T. and Kijima, S. (1969) US 3 459 774 (Eisai Co.); (b) Grant, P.M. (1970) US 3 538 119 (Eastman Kodak Co.).
- 146Blind, A. and Sagi, F. (1988) FR 2 602 772 (Rhône-Poulenc-Santé).
- 147Chernikov, G.S., Baranova, N.G., Azizov, U.M. and Afanasev, I.B. (1988) Khim.-Farm. Zh. 22, 1244–1253.
- 148(a) Arnold, A., Pasedach, H. and Pommer H. (1971) DE 1 668 874 (Badische Anilin- & Soda-Fabrik AG); (b) Jouffret, M. (1975) DE 2 450 908 (Rhône-Poulenc S.A.).
- 149(a) Brenner, W. (1972) DE 2 221 624 (F. Hoffmann-La Roche & Co. AG); (b) Bartoldus, D. and Lohri, B. (1981) EP 35 635 (F. Hoffmann-La Roche & Co. Aktiengesellschaft); (c) Tamura, M., Yamamoto, H. and Yoshimura, N. (1980) JP 55 072 136 (Kuraray Co.); (d) Hsu, C.Y. and Lyons, J.F. (1983) EP 0 070 665 (Sun Tech, Inc.); (e) Thoemel, F. and Hoffmann, W. (1983) EP 0 093 880 (BASF Aktiengesellschaft); (f) Bockstiegel, B., Hoercher, U., Laas, H., et al. (1992) DE 4 029 198 (BASF AG); (g) Isshiki, T., Yui, T., Uno, H. and Abe, M. (1984) EP 127 888 (Mitsubishi Gas Chemical Co., Inc.); (h) Hirose, N., Hamamura, K., Inai, Y., et al. (1988) EP 294 584 (Eisai Co.); (i) Takehira, K., Orita, H., Shimizu, M., et al. (1990) EP 369 823 (Jpn. Agency of Industr. Science and Technol.); (j) Griggs, C.G. (1986) EP 175 574 (British Petroleum Company).
- 150Shimizu, M., Watanabe, Y., Orita, H., et al. (1992) Bull. Chem. Soc. Jpn. 65, 1522–1526.
- 151Fujibayashi, S., Nakayama, K., Nishiyama, Y. and Ishii, Y. (1994) Chem. Lett. 23, 1345–1348.
- 152Kholdeeva, O.A., Golovin, A.V., Maksimovskaya, R.I. and Kozhevnikov, I.V. (1992) J. Mol. Catal. 75, 235–244.
- 153Lissel, H., Jansen in deWal, H. and Neumann, R. (1992) Tetrahedron Lett. 33, 1795–1798.
- 154Shimizu, M., Orita, H., Hayakawa, T. and Takehira, K. (1989) Tetrahedron Lett. 30, 471–474.
- 155Shimizu, M., Takehira, K., Hayakawa, T., et al. (1989) EP 338 666 (Jpn. Agency Ind. Sci. Technol.).
- 156(a) Schuster, L. (1971) DE 1 940 386 (Badische Anilin- & Soda-Fabrik AG); (b) Kawaguchi, T., Nishida, T., Ohmura, Y., et al. (1973) DE 2 250 066 (Kuraray Co.); (c) Tamai, Y. and Itoi, K. (1973) DE 2 309 051 (Kuraray Co.); (d) Höver, H. and Biller, E. (1973) DE 2 225 543 (Union Rheinische Braunkohlen Kraftstoff AG); (e) Broecker, F.J., Tavs, P., Laas, H. and Aders, W.-K. (1985) EP 152 842 (BASF Aktiengesellschaft); (f) Yui, T., Ito, A. and Takata, T. (1986) EP 198 476 (Mitsubishi Gas Chem. Comp.); (g) Yui, T. and Ito, A. (1986) EP 264 823 (Mitsubishi Gas Chem. Comp.).
- 157Wang, Z., Mao, S., Li, H. and Wang, Y. (2018) Acta Phys.-Chim. Sin. 34, 598–617. doi: 10.3866/PKU.WHXB201711231.
- 158(a) Brenner, W., Hinderling, R. and Lindlar, H. (1974) DE 2 415 930 (F. Hoffmann-La Roche); (b) Ito, M. (1991) EP 419 045 (Mitsubishi Gas Chem. Comp.); (c) Sakai, K. and Oohashi, H. (1994) JP 6116189 (Asahi Chem. Ind. Co.).
- 159(a) Arnold, L., Pasedach, H. and Pommer, H. (1971) DE 1 793 037 (Badische Anilin- & Soda-Fabrik AG); (b) Wehrli, P.A. (1974) US 3 857 892 (Hoffmann-La Roche Inc.).
- 160Arnold, L. (1971) DE 1 668 874 (Badische Anilin- & Soda-Fabrik AG).
- 161Wehrli, P.A., Fryer, R.I., Pigott, F. and Silverman, G. (1972) J. Org. Chem. 37, 2340–2343.
- 162Bushmelev, V.A., Kondrat'eva, T.A., Lipkin, M.A. and Kondrat'ev, A.V. (1991) Khim.-Farm. Zh. 25, 65–73.
- 163Ichikawa, Y., Yamanaka, Y. and Tsuruta, H. (1976) CH 573 883 (Teijin Ltd.).
- 164Ichikawa, Y., Yamanaka, Y., Suzuki, N., et al. (1979) Ind. Eng. Chem. Prod. Res. Dev. 18, 373–375.
- 165(a) Constantini, M., Igersheim, F. and Krumenacker, L. (1986) US 4 612 401 (Rhone-Poulenc Sante); (b) Yoshida, D. (1987) JP 62 192 337 (C. K. Fine Chemicals); (c) Tomita, T., Masahiro, J. and Toshiaki, T. (1983) EP 84 158 (Mitsubishi Gas Chem. Comp.); (d) Masahiro, K., Tomoyuki, Y., Tomiya, I. and Muneo, I. (1984) JP 59 227 835 (Kuraray Co.); (e) Tomita, T., Masahiro, J. and Takata, T. (1984) US 4 477 682 (Mitsubishi Gas Chem. Comp.).
- 166(a) Ichikawa, Y., Yamanaka, Y. and Tsuruta, H. (1974) DE 2 345 062 (Teijin Ltd.); (b) Kunitomi, H. and Tamai, H. (1987) JP 62 263 136 (Kuraray Co.).
- 167Mercier, C. and Chabardes, P. (1994) Pure Appl. Chem. 66, 1509–1518.
- 168Mercier, C. and Chabardes, P. (1995) Chem. Ind. (Dekker) 62, 213–222.
- 169Wüstenberg, B., Bonrath, W., Netscher, T., et al. (2015) WO 2 015 169 898 (DSM IP Assets B.V.).
- 170Bonrath, W., Netscher, T., Schütz, J., et al. (2012) WO 2 012 025 587 (DSM IP Assets B.V.).
- 171Hiramine, T. and Ogura, S. (2006) JP 2 006 249 036 (Honshu Chem. Ind. Co. Ltd.).
- 172Michelet, D. (1974) DE 2 418 342 (Rhone-Poulenc S.A.).
- 173Jouffret, M. (1975) DE 2 518 028 (Rhone-Poulenc Ind.).
- 174(a) Baudouin, M.M. and Perron, R.M. (1981) US 4 247 720 (Rhone-Poulenc Ind.); (b) Thweatt, J.G. and Rash, F.H. (1972) DE 2 149 159 (Eastman Kodak Co.).
- 175Joe, Y.A., Goo, Y.M. and Lee, Y.Y. (1991) Bull. Korean Chem. Soc. 12, 253–254.
- 176Krill, S. and Huthmacher, K. (2001) EP 1 028 103 (Degussa-Hüls Aktiengesellschaft).
- 177Bonrath, W. and Schneider, M. (2003) WO 03 051 812 (Roche Vitamins AG).
- 178Aquino, F, Bonrath, W. and Pace, F. (2005) WO 05 044 775 (DSM IP Assets B.V.).
- 179Wang, C., Li, H., Hu, B., et al. (2009) CN 101 607 896 (Zhejiang University).
- 180Cao, K., Duan, W., Liu, H., et al. (2018) CN 108 047 042 (Zhejiang NHU Pharmaceutical Co. Ltd.).
- 181Song, W., Zeng, Q., Zhang, Q., et al. (2011) CN 102 180 793 (Zhejiang NHU Pharmaceutical Co. Ltd.).
- 182Guo, J., Huang, Z., Zhang, T., et al. (2020) CN 111 393 290 (Wanhua Chemical Group Co., Ltd.).
- 183Saucy, G. and Marbet, R. (1967) Helv. Chim. Acta 50, 2091–2095.
- 184(a) Pasedach, H. and Seefelder, M. (1959) DE 1 068 696 (Badische Anilin- & Soda-Fabrik Aktiengesellschaft); (b) Pasedach, H. and Seefelder, M. (1960) DE 1 073 476 (Badische Anilin- & Soda-Fabrik Aktiengesellschaft); (c) Nissen, A., Kaibel, G., Woerz, O., et al. (1982) US 4 310 705 (BASF Aktiengesellschaft); (d) Kimel, W. (1953) US 2 628 250 (Hoffmann-La Roche Inc.); (e) Kimel, W. (1953) US 2 638 484 (Hoffmann-La Roche Inc.); (f) Kimel, W. (1953) US 2 660 608 (Hoffmann-La Roche Inc.); (g) Kimel, W. and Sax, N.W. (1957) US 2 795 617 (Hoffmann-La Roche Inc.).
- 185Hoffmann, W., Pasedach, H. and Pommer, H. (1969) Justus Liebigs Ann. Chem. 729, 52–63.
- 186Hoffmann, W. (1973) Chem.-Ztg. 97, 23–28.
- 187Carroll, M.F. (1940) J. Chem. Soc. 704–706.
- 188Carroll, M.F. (1940) J. Chem. Soc. 1266–1268.
- 189Carroll, M.F. (1941) J. Chem. Soc. 507–511.
- 190Saucy, G. and Marbet, R. (1967) Helv. Chim. Acta 50, 1158–1167.
- 191Saucy, G. and Marbet, R. (1967) Helv. Chim. Acta 50, 2095–2100.
- 192Marbet, R. and Saucy, G. (1960) Versammlungsberichte, Angew. Chem. 72, 868–869.
- 193Paust, J. (1991) Pure Appl. Chem. 63, 45–58.
- 194Bonrath, W., Medlock, J., Schütz, J., et al. (2012) Chapt. 3 Hydrogenation in the Vitamins and Fine Chemicals Industry, in Hydrogenation, (ed. I. Karamé), InTech, Rijeka, Croatia, pp. 69–90.
10.5772/48751 Google Scholar
- 195Bonrath, W., Kircher, T., Künzi, R. and Tschumi, J. (2006) WO 2 006 029 737 (DSM IP Assets B.V.).
- 196Lindlar, H. (1952) Helv. Chim. Acta 35, 446–450.
- 197(a) Lindlar, H. and Dubuis, R. (1966) Org. Synth. 46, 89. (b) Lindlar, H., Dubuis, R., Checked by Jones, F.N and McKusick, B.C. (1973) Org. Synth., Coll. Vol. 5, 880.
- 198Bruehwiler, A., Semagina, N., Grasemann, M., et al. (2008) Ind. Eng. Chem. Res. 47, 6862–6869.
- 199Bonrath, W., Mueller, T., Kiwi-Minsker, L., et al. (2011) WO 2 011 092 280 (DSM IP Assets B.V.).
- 200Altheimer, M., Bonrath, W., Goy, R., et al. (2018) WO 2 018 202 640 (DSM IP Assets B.V.).
- 201Itoi, K. (1992) Organic Synthesis in Japan, Past, Present, and Future, (ed. R. Noyori), Tokyo Kagaku Dozin, Tokyo, p. 165.
- 202(a) Morel, D. (1982) EP 44 771 (Rhone-Poulenc Ind.); (b) Chabardes, P. and Mercier, C. (1991) EP 441 708 (Rhone-Poulenc Rohrer S.A.).
- 203Mignani, G., Morel, D. and Colleuille, Y. (1985) Tetrahedron Lett. 26, 6337–6340.
- 204Mercier, C., Mignani, G., Aufrand, M. and Allmang, G. (1991) Tetrahedron Lett. 32, 1433–1436.
- 205Dai, Q., Zheng, Y., Chen, Q., et al. (2016) CN 105 859 534 (Faming Zhuanli Shenqing).
- 206Schelwies, M., Paciello, R., Eckhardt, H. and Dehn, M. (2015) US 10 093 606 (BASF SE).
- 207Dai, Q., Zhen, Y., Chen, L., et al. (2016) CN 105 944 768 (Nenter & Co., Inc.).
- 208Meadows, A.L., Hawkins, K.M., Tsegaye, Y., et al. (2016) Nature 537, 694–697.
- 209Kaib, P.S.J. and List, B. (2016) Synlett 27, 156–158.
- 210Saucy, G. and Cohen, N. (1981) Asymmetric Reactions Applied to the Synthesis of d-α-Tocopherol, in New Synthetic Methodology and Biologically Active Substances, (ed. Z. Yoshida), Elsevier, Amsterdam, pp. 155–175.
- 211Netscher, T. (1996) Chimia 50, 563–567.
- 212Netscher, T. (1999) Synthesis and Production of Vitamin E, in Lipid Synthesis and Manufacture, (ed. F.D. Gunstone), Sheffield Academic Press Ltd., Sheffield, UK, pp. 250–267.
- 213Netscher, T. (2007) Vitam. Horm. 76, 155–202.
- 214Netscher, T. (2014) Angew. Chem. Int. Ed. 53, 14313–14315.
- 215Netscher, T. (2019) Chimia 72, 485–491.
- 216Tani, K., Yamagata, T. and Akutagawa, et al. (1984) J. Am. Chem. Soc. 106, 5208–5217.
- 217Schmid, R., Cereghetti, M., Heiser, B., et al. (1988) Helv. Chim. Acta 71, 897–929.
- 218Takaya, H., Ohta, T., Sayo, N., et al. (1987) J. Am. Chem. Soc. 109, 1596–1597.
- 219Noyori, R. and Takaya, H. (1990) Acc. Chem. Res. 23, 345–350.
- 220Schmid, R., and Broger, E.A. (1994) Asymmetric hydrogenation in process research of pharmaceuticals, vitamins and fine chemicals, Proceedings of the Chiral Europe ‘94 Symposium, 19–20 Sept. 1994, Nice, France, pp. 79–86.
- 221Schmid, R., Broger, E.A., Cereghetti, M., et al. (1996) Pure Appl. Chem. 68, 131–138.
- 222Schmid, R. (1996) Chimia 50, 110–113.
- 223Netscher, T., Scalone, M. and Schmid, R. (2003) Enantioselective Hydrogenation: Towards a Large-scale Total Synthesis of (R,R,R)-α-Tocopherol, in Asymmetric Catalysis on Industrial Scale, (eds. H.U. Blaser and E. Schmidt), 1st edn, Wiley-VCH Verlag, Weinheim, Germany, pp. 71–89.
10.1002/3527602151.ch4 Google Scholar
- 224Bell, S., Wüstenberg, B., Kaiser, S., et al. (2006) Science 311, 642–644.
- 225Bonrath, W., Menges, F., Netscher, T., Pfaltz, A. and Wüstenberg, B. (2006) WO 2 006 066 863 (DSM IP Assets B.V.).
- 226Wang, A., Wüstenberg, B. and Pfaltz, A. (2008) Angew. Chem. Int. Ed. 47, 2298–2300.
- 227 DSM IP Assets B.V., (2014) WO 14 096 063, WO 14 096 065, WO 14 096 067, WO 1 496 096, WO 1 496 098, WO 1 496 106, WO 1 496 107, WO 1 497 170, WO 1 497 171, WO 14 096 066, WO 14 097 172, WO 14 097 173.
- 228Stocker, A., Fretz, H., Frick, H., et al. (1996) Bioorg. Med. Chem. 4, 1129–1134.
- 229Chougnet, A., Liu, K. and Woggon, W.-D. (2010) Chimia 64, 303–308, and references cited therein.
- 230Liu, K., Chougnet, A. and Woggon, W.-D. (2008) Angew. Chem. Int. Ed. 47, 5827–5829.
- 231Grütter, C., Alonso, E., Chougnet, A. and Woggon, W.-D. (2006) Angew. Chem. Int. Ed. 45, 1126–1130.
- 232Tietze, L.F., Stecker, F., Zinngrebe, J. and Sommer, K.M. (2006) Chem. Eur. J. 12, 8770–8776.
- 233Tietze, L.F. and Kinzel, T. (2007) Pure Appl. Chem. 79, 629–650.
- 234Trost, B.M. (2004) J. Org. Chem. 69, 5813–5837.
- 235Trost, B.M., Shen, H.C., Dong, L., et al. (2004) J. Am. Chem. Soc. 126, 11966–11983.
- 236Uria, U., Vila, C., Lin, M.-Y. and Rueping, M. (2014) Chem. Eur. J. 20, 13913–13917.
- 237Rein, C., Demel, P., Outten, R.A., et al. (2007) Angew. Chem. Int. Ed. 46, 8670–8673.
- 238Uyanik, M., Hayashi, H. and Ishihara, K. (2014) Science 345, 291–294.
- 239Termath, A.O., Sebode, H., Schlundt, W., et al. (2014) Chem. Eur. J. 20, 12051–12055.
- 240Wu, Z., Harutyunyan, S.R. and Minnaard, A.J. (2014) Chem. Eur. J. 20, 14250–14255.
- 241Huo, S. and Negishi, E.-i. (2001) Org. Lett. 3, 3253–3256.
- 242Matsueda, Y., Xu, S. and Negishi, E.-i. (2015) Tetrahedron Lett. 56, 3346–3348.
- 243(a) Bieszczad, B. and Gilheany, D.G. (2017) Org. Biomol. Chem. 15, 6483–6492. (b) Bieszczad, B. and Gilheany, D.G. (2017) Angew. Chem. Int. Ed. 56, 4272–4276.
- 244Ratsch, F., Schlundt, W., Albat, D., et al. (2019) Chem. Eur. J. 25, 4941–4945.
- 245Cohen, A., Chagneau, J. and Marek, I. (2020) ACS Catal. 10, 7154–7161.
- 246Halliwell, B. and Gutteridge, J.M.C. (2015) Free Radicals in Biology & Medicine, 5th edn, Oxford University Press, Oxford.
10.1093/acprof:oso/9780198717478.001.0001 Google Scholar
- 247Burton, G.W. and Ingold, K.U. (1989) Vitamin E: Biochemistry and Health Implications, Part I. Chemistry and Antioxidant Functions, Ann. N.Y. Acad. Sci. 570 (1), 7–22.
- 248Kayden, H.J. and Traber, M.G. (1993) J. Lipid Res. 34, 343–358.
- 249Traber, M.G. and Atkinson, J. (2007) Free Radic. Biol. Med. 43, 4–15.
- 250Brigelius-Flohé, R. (2006) Nutr. Res. Rev. 19, 174–186.
- 251Meier, R., Tomizaki, T., Schulze-Briese, C., et al. (2003) J. Mol. Biol. 331, 725–734.
- 252Christen, S., Woodall, A.A., Shigenaga, M.K., et al. (1997) Proc. Natl. Acad. Sci. USA 94, 3217–3222.
- 253Gallo-Torres, H.E. (1980) Vitamin E – A Comprehensive Treatise, Part 5B, Transport and Metabolism, (ed. L.J. Machlin), Marcel Dekker, New York, pp. 193–267.
- 254Reboul, E., Klein, A., Bietrix, F., et al. (2006) J. Biol. Chem. 281, 4739–4745.
- 255Gey, K.F. and Puska, P. (1988) Vitamin E: Biochemistry and Health Implications, Part IV. Ischemia-Reperfusion Injury: Cardiovascular Disease, Ann. N.Y. Acad. Sci. 570 (1), 268–282.
- 256Horwitt, M.K. (1980) Nutr. Rev. 38, 105–113.
- 257Walton, J.R. and Packer, L. (1980) Vitamin E – A Comprehensive Treatise, Part 10B, Free Radical Damage and Protection: Relationship to Cellular Aging and Cancer, (ed. L.J. Machlin), Marcel Dekker, New York, pp. 495–517.
- 258Panush, R.S. and Delafuente, J.C. (1985) World Rev. Nutr. Diet. 45, 97–132.
- 259Traber, M.G. (2014) Chapt. 4 Vitamin E, in Handbook of Vitamins, (eds. J. Zempleni, J.W. Suttie, J.F. Gregory and P.J. Stover), 5th edn, CRC Press, Boca Raton, FL, pp. 125–147.
- 260Kayden, H.J. (1993) Neurology 43, 2167–2169.
- 261 Institute of Medicine (IOM), Food and Nutrition Board (2000) Dietary Reference Intake for Vitamin C, Vitamin E, Selenium, and Carotenoids, The National Academies Press, Washington, DC. doi: 10.17226/9810 (accessed 29 July 2020).
10.17226/9810 Google Scholar
- 262Bo, H., Li, D., Sawamura, T., et al. (2003) Biochem. Biophys. Res. Commun. 307, 1008–1012.
- 263Sanyal, A.J., Chalasani, N., Kowdley, K.V., et al. (2010) New Engl. J. Med. 362, 1675–1685.
- 264Lavine, J.E., Schwimmer, J.B., Van Natta, M.L., et al. (2011) JAMA J. Am. Med. Assoc. 305, 1659–1668.
- 265Howard, A.C., McNeil, A.K. and McNeil, P.L. (2011) Nat. Commun. 2, 597. doi: 10.1038/ncomms1594.
- 266Labazi, M., McNeil, A.K., Kurtz, T., et al. (2015) Free Rad. Biol. Med. 84, 246–253.
- 267Ricciarelli, R., Zingg, J.-M. and Azzi, A. (2000) Circulation 102, 82–87.
- 268Devaraj, S., Tang, R., Adams-Huet, B., et al. (2007) Am. J. Clin. Nutr. 86, 1392–1398.
- 269Freedman, J.E., Farhat, J.H., Loscalzo, J. and Keaney, J. (1996) Circulation 94, 2434–2440.
- 270Rimbach, G., Fischer, A., Stoecklin, E. and Barella, L. (2004) Ann. N.Y. Acad. Sci. 1031, 102–108.
- 271Rota, C., Rimbach, G., Minihane, A.-M., et al. (2005) Nutr. Neurosci. 8, 21–29.
- 272Nier, B., Weinberg, P.D., Rimbach, G., et al. (2006) IUBMB Life 58, 540–548.
- 273Han, S.N., Pang, E., Zingg, J.-M., et al. (2010) Arch. Biochem. Biophys. 495, 49–55.
- 274Zingg, J.-M. and Azzi, A. (2004) Curr. Med. Chem. 11, 1113–1133.
- 275Idamokoro, E.M., Falowo, A.B., Oyeagu, C.E. and Afolayan, A.J. (2020) Animal Sci. J. 91, e13352.
- 276 FEFANA Publication (2014) Vitamins in Animal Nutrition, pp. 110–111, ISBN 978-2-9601289-2-5, corrigendum of 30 Oct. 2015; booklet can be downloaded from: https://fefana.org/publication/vitamins-in-animal-nutrition/ (accessed 14 May 2020).
- 277Abidi, S.L. (2000) J. Chromatogr. A 881, 197–216.
- 278Desai, I.D. (1980) Part 3, Assay Methods, in Vitamin E – A Comprehensive Treatise, (ed. L.J. Machlin), Marcel Dekker, New York, pp. 68–98.
- 279Nelis, H.J., D'Haese, E. and Vermis, K. (2000) Chapt. 3, Vitamin E, in Modern Chromatographic Analysis of the Vitamins, (eds. A.P. Leenheer, W.E. Lambert and J.F. Bocxlaer), 3rd edn, Marcel Dekker, New York, pp. 154–239.
- 280Shin, T.-S. and Godber, J.S. (1993) J. Am. Oil Chem. Soc. 70, 1289–1291.
- 281Schüep, W. and Rettenmaier, R. (1994) Methods Enzymol. 234, 294–302.
- 282Pinheiro-Sant'Ana, H.M., Guinazi, M., da Silva Oliveira, D., et al. (2011) J. Chromatogr. A 1218, 8496–8502.
- 283Emmerie, A. and Engel, C. (1938) Recl. Trav. Chim. Pays-Bas 57, 1351–1355.
- 284Tsen, C.C. (1961) Anal. Chem. 33, 849–851.
- 285Vatassery, G.T. and Mortenson, G.A. (1972) Clin. Chem. (Winston Salem, N.C.) 18, 1475–1477.
- 286Taylor, S.L., Lamden, M.P. and Tappel, A.L. (1976) Lipids 11, 530–538.
- 287Boguth, W. and Repges, R. (1969) Int. Z. Vitaminforsch. 39, 289–295.
- 288Linow, F. and Pohl, J. (1970) Nahrung 14, 269–278.
- 289Bremser, W. and Vogel, F.G.M. (1980) Org. Magn. Reson. 14, 155–156.
- 290Lankhorst, P.P., Netscher, T. and Duchateau, A.L.L. (2015) Chirality 27, 850–855.
- 291Vecchi, M., Walther, W., Glinz, E., et al. (1990) Helv. Chim. Acta 73, 782–789.
- 292Riss, G., Kormann, A.W., Glinz, E., et al. (1994) Methods Enzymol. 234, 302–310.
- 293Jensen, S.K. and Lauridsen, C. (2007) Vitam. Horm. 76, 281–308.
- 294Ames, S.R., Ludwig, M.I., Nelan, D.R. and Robeson, C.D. (1963) Biochemistry 2, 188–190.
- 295Weiser, H., Vecchi, M. and Schlachter, M. (1986) Int. J. Vitam. Nutr. Res. 56, 45–56.
- 296Scott, M.L. and Desai, I.D. (1964) J. Nutr. 83, 39–43.
- 297Machlin, L.J., Gabriel, E. and Brin, M. (1982) J. Nutr. 112, 1437–1440.
- 298Brueggemann, J., Niesar, K.H. and Zentz, C. (1963) Int. Z. Vitaminforsch. 33, 180–196.
- 299Horwitt, M.K. (1960) Am. J. Clin. Nutr. 8, 451–461.
- 300 Food and Nutrition Board, National Research Council, National Academy of Sciences (1968) Recommended Dietary Allowances, National Academy of Sciences, Washington, DC National Formulary 14 (1975) 758; Remark: We were unable to retrieve the full contents of this old reference cited in the former version of (Ullmann o27_o07).
- 301(a) Ames, S.R. (1979) J. Nutr. 109, 2198–2204. (b) Weiser, H. and Vecchi, M. (1982) Int. J. Vitam. Nutr. Res. 52, 351–370.
- 302Hosomi, A., Arita, M., Sato, Y., et al. (1997) FEBS Lett. 409, 105–108.
- 303 Institute of Medicine (IOM), Food and Nutrition Board (2000) Dietary Reference Intake for Vitamin C, Vitamin E, Selenium, and Carotenoids, The National Academies Press, Washington, DC. doi: 10.17226/9810 (accessed 29 July 2020). Table 6-1. Factors for Converting International Units of Vitamin E to α-Tocopherol, p. 192.
10.17226/9810 Google Scholar
- 304 National Institutes of Health, https://www.nih.gov/, search NIH “unit conversions”; https://dietarysupplementdatabase.usda.nih.gov/Conversions.php (Dietary Supplement Ingredient Database) (accessed 30 July 2020).
