The Vitamins. Chemistry, Physiology, Pathology PDF
Preview The Vitamins. Chemistry, Physiology, Pathology
THF VITAMINS Chemistry, Physiology, Pathology VOLUME III EDITED BY W. H. SEBRELL, JR. ROBERT S. HARRIS Director, National Institutes of Health Professor of Biochemistry of Nutrition Bethesda, Maryland Massachusetts Institute of Technology Cambridge, Massachusetts @ ACADEMIC PRESS, INC., PUBLISHERS New York · 1954 Copyright, 1954, by ACADEMIC PRESS, INC. 125 East 23rd Street New York 10, N. Y. All Rights Reserved NO PART OF THIS BOOK MAY BE REPRODUCED IN ANY FORM, BY PHOTOSTAT, MICROFILM, OR ANY OTHER MEANS WITHOUT WRITTEN PERMISSION FROM THE PUBLISHERS Library of Congress Catalog Card Number: 54-7612 PRINTED IN THE UNITED STATES OF AMERICA CONTRIBUTORS TO VOLUME III FRANK H. BETHELL (202-217)* CHARLES S. KEEVIL, JR. (255-263) University of Michigan Department of Chemistry The Thomas Henry Simpson Memorial University of Texas Institute for Medical Research Austin 12, Texas Ann Arbor, Michigan JOHN C. KEREZTESY (222-233) VERNON H. CHELDELIN (575-600) National Institutes of Health Professor of Chemistry Public Health Service Oregon State College Bethesda 14, Maryland School of Science KARL E. MASON (514-570, 572-573) Corvallis, Oregon Department of Anatomy P. GYÖRGY (280-290, 298) School of Medicine and Dentistry University of Pennsylvania Hospital University of Rochester 3400 Spruce Street Rochester, New York Philadelphia 4, Pennsylvania HENRY A. MATTILL (483-495, 501-514, PHILIP L. HARRIS (495-501) 570-572) Biochemistry Department Department of Biochemistry Distillation Products Industries College of Medicine Rochester 3, New York State University of Iowa Iowa City, Iowa ROBERT S. HARRIS (2, 121-124, 220-221, 300-301, 404, 482-483) CHARLES C. SCOTT (52-62) Department of Food Technology Director of Pharmacology Massachusetts Institute of Technology Chilcott Laboratories Cambridge 39, Massachusetts The Maltine Company D. M. HEGSTED (361-371) Morris Plains, New Jersey Department of Nutrition W. H. SEBRELL, JR. (478-480) School of Public Health Director Harvard University National Institutes of Health Boston 15, Massachusetts Bethesda, Maryland M. K. HORWITT (334-361, 373-377, 379- 402) HENRY SHERMAN (243-253, 255, 264-276, Elgin State Hospital 293-298) Director, Biochemical Research Labo- Department of Food Technology ratory Massachusetts Institute of Technology Elgin, Illinois Cambridge 39, Massachusetts B. C. P. JANSEN (404-409, 425-466, 472- ESMOND E. SNELL (253-263, 276-280, 372- 478) 373, 377-379) Nederlands Institut voor Volksvoeding Department of Chemistry J. D. Meyeroldin 3 University of Texas Amsterdam, Holland Austin 12, Texas * Numbers in parentheses indicate the pages on ich each author's contribution or contributions may be found V VI CONTRIBUTORS E. L. R. STOKSTAD (89-121, 124-202) LEMUEL D. WRIGHT (2-12, 13-52, 62-85) Lederle Laboratories Director of Research in Microbiolog- Pearl River, New York ical Chemistry Research Division PETER A. TAVORMINA (2-12,13-52,62-85) Sharp and Dohme Sharp and Dohme West Point, Pennsylvania West Point, Pennsylvania W. W. UMBREIT (239-242) THEODOR WAGNER-JAUREGG (301-333) Merck Therapeutic Institute Medical Division Rahway, New Jersey Army Medical Center KLAUS R. UNNA (290-293, 466-471) Edgewood, Maryland Department of Pharmacology Medical School H. M. WUEST (12-13, 409-425) University of Illinois 137 Summit Avenue Chicago, Illinois Montclair, New Jersey CONTENTS OF VOLUME I AND II VOLUME I VOLUME II CHAPTER 5. CHOLINE CHAPTER 1. VITAMINS A AND Charles H. Best, Wendell H. Griffith, CAROTENES Robert S. Harris, W. Stanley Hartroft, Robert S. Harris, H.H. Inhoffen, Karl Colin C. Lucas, Joseph F. Nyc E. Mason, F. H. Mattson, Nicholas A. CHAPTER 6. VITAMIN D GROUP Milas, H. Pommer, George Wald, Charles E. Bills, Robert S. Harris, S. Hurt Wolbach James H. Jones, Abram Kanof, Benja- min Kramer CHAPTER 7. ESSENTIAL FATTY ACIDS CHAPTER 2. ASCORBIC ACID George A. Emerson, Arild E. Hansen, Robert S. Harris, L. W. Mapson, Robert S. Harris, Ralph T. Holman, Hilda F. Wiese Mamie Olliver, Mary Elizabeth Reid, Fred Smith, Richard W. Vilter CHAPTER 8. INOSITOLS Erwin Char gaff, T. J. Cunha, Robert S. Harris, Henry A. Lardy, Arthur H. Livermore, A. T. Milhorat, Esmond E. CHAPTER 3. VITAMIN Bu Snell, E. R. Weidlein, Jr. Frank H. Bethell, Karl E. Folkers, CHAPTER 9. VITAMIN K GROUP Robert S. Harris, Thomas H. Jukes, H. J. Almquist, Robert S. Harris, Charles A. Owen, Jr. William L. Williams, Donald E. Wolf CHAPTER 10. NIACIN Robert S. Harris, James M. Hundley, Esmond E. Snell CHAPTER 4. BIOTIN CHAPTER 11. PANTOTHENIC ACID Paul Gybrgy, Robert S. Harris, Esmond George M. Briggs, Floyd S. Daft, Robert E. Snell S. Harris, Samuel Lepkovsky, Fritz Lipmann, Elaine P. Ralli, Esmond E. Snell Author Index—Subject Index Author Index—Subject Index CHAPTER 12 p-AMINOBENZOIC ACID Page I. Nomenclature 2 II. Chemistry 2 A. Preparation 2 B. Physical Properties 3 C. Chemical Properties 6 D. Derivatives 10 E. Color Reactions 11 III. Industrial Preparation 12 IV. Biochemical Systems 13 V. Biogenesis 16 VI. Estimation 19 A. Chemical Methods 19 B. Microbiological Methods 21 VII. Occurrence in Foods 27 VIII. Effects of Deficiency 32 A. In Bacteria 32 1. Nutrition 32 2. Synthesis 34 B. In Animals 37 1. Rats 37 2. Mice 41 3. Hamsters 42 4. Chicks 42 5. Swine 42 6. Fish 43 IX. Metabolism 43 A. Excretion in Lower Animals 43 B. Excretion in Human Beings 46 X. Toxicity 49 A. In Laboratory Animals 49 B. In Human Beings 51 XI. Pharmacology 52 A. Absorption, Fate, and Excretion 52 B. Toxicity 53 C. Pharmacological Actions 55 1. Circulatory System 55 2. Blood 55 3. Gastrointestinal Tract 55 4. Nervous System 56 5. Muscle 56 6. Enzyme Systems 56 7. Endocrine System 57 8. Detoxicating Action 58 1 2 P-AMINOBENZOIC ACID Page D. Therapeutic Uses 59 1. Gray Hair 59 2. Dermatology 60 3. Rickettsial Diseases 60 4. Neoplastic Diseases 61 5. Other Diseases 61 XII. Detoxication of Arsenicale 62 XIII. Sulfonamide Reversal 66 XIV. Therapeutic Activity 79 A. Rickettsial Diseases 79 B. Rheumatoid Diseases 81 C. Achromotrichia 83 D. Thyrotoxicosis 84 E. Miscellaneous Diseases 85 I. Nomenclature ROBERT S. HARRIS Accepted name: p-Aminobenzoic acid Obsolete names: Vitamin B Anti-gray hair factor x B factor Trichochromogenic factor x Chromotrichia factor Bacterial growth factor P Anticanitic vitamin Bacterial vitamin H Empirical formula: C7H7NO2 Chemical name: 4-Aminobenzoic acid Structure: H N—? \— CO OH 2 II· Chemistry LEMUEL D. WRIGHT and PETER A. TAVORMINA A. PREPARATION Both reductive and oxidative methods have been used in the synthesis of p-aminobenzoic acid (PABA). The chemical reduction of p-nitrobenzoic acid has been effected with ammonium sulfide,1 tin and hydrochloric acid,2·3 ferrous sulfate and am- 1 G. Fischer, Ann. 127, 137 (1863). 2 J. Wilbrand and F. Beilstein, Ann. 128, 257 (1863). 3E. Widnmann, Ann. 193, 202 (1878). 2 P-AMINOBENZOIC ACID Page D. Therapeutic Uses 59 1. Gray Hair 59 2. Dermatology 60 3. Rickettsial Diseases 60 4. Neoplastic Diseases 61 5. Other Diseases 61 XII. Detoxication of Arsenicale 62 XIII. Sulfonamide Reversal 66 XIV. Therapeutic Activity 79 A. Rickettsial Diseases 79 B. Rheumatoid Diseases 81 C. Achromotrichia 83 D. Thyrotoxicosis 84 E. Miscellaneous Diseases 85 I. Nomenclature ROBERT S. HARRIS Accepted name: p-Aminobenzoic acid Obsolete names: Vitamin B Anti-gray hair factor x B factor Trichochromogenic factor x Chromotrichia factor Bacterial growth factor P Anticanitic vitamin Bacterial vitamin H Empirical formula: C7H7NO2 Chemical name: 4-Aminobenzoic acid Structure: H N—? \— CO OH 2 II· Chemistry LEMUEL D. WRIGHT and PETER A. TAVORMINA A. PREPARATION Both reductive and oxidative methods have been used in the synthesis of p-aminobenzoic acid (PABA). The chemical reduction of p-nitrobenzoic acid has been effected with ammonium sulfide,1 tin and hydrochloric acid,2·3 ferrous sulfate and am- 1 G. Fischer, Ann. 127, 137 (1863). 2 J. Wilbrand and F. Beilstein, Ann. 128, 257 (1863). 3E. Widnmann, Ann. 193, 202 (1878). 2 P-AMINOBENZOIC ACID Page D. Therapeutic Uses 59 1. Gray Hair 59 2. Dermatology 60 3. Rickettsial Diseases 60 4. Neoplastic Diseases 61 5. Other Diseases 61 XII. Detoxication of Arsenicale 62 XIII. Sulfonamide Reversal 66 XIV. Therapeutic Activity 79 A. Rickettsial Diseases 79 B. Rheumatoid Diseases 81 C. Achromotrichia 83 D. Thyrotoxicosis 84 E. Miscellaneous Diseases 85 I. Nomenclature ROBERT S. HARRIS Accepted name: p-Aminobenzoic acid Obsolete names: Vitamin B Anti-gray hair factor x B factor Trichochromogenic factor x Chromotrichia factor Bacterial growth factor P Anticanitic vitamin Bacterial vitamin H Empirical formula: C7H7NO2 Chemical name: 4-Aminobenzoic acid Structure: H N—? \— CO OH 2 II· Chemistry LEMUEL D. WRIGHT and PETER A. TAVORMINA A. PREPARATION Both reductive and oxidative methods have been used in the synthesis of p-aminobenzoic acid (PABA). The chemical reduction of p-nitrobenzoic acid has been effected with ammonium sulfide,1 tin and hydrochloric acid,2·3 ferrous sulfate and am- 1 G. Fischer, Ann. 127, 137 (1863). 2 J. Wilbrand and F. Beilstein, Ann. 128, 257 (1863). 3E. Widnmann, Ann. 193, 202 (1878). II. CHEMISTRY 3 monia,4 or sodium hydrosulfide.5 Catalytic hydrogénation6 has been carried out with platinum oxide as catalyst. More recently, Ravenscroft and his associates7 employed electrolytic reduction of the nitro compound to pre- pare PABA in very high yields. The oxidation of p-acetotoluide offers an alternative route for the prepa- ration of PABA. Potassium8 or calcium9 permanganate has been used for this purpose. Hydrolysis of the p-acetamidobenzoic acid with mineral acid yields the amino compound. Of special interest are the syntheses leading to isotope-labeled PABA. Murray and his collaborators10 have described a reaction whereby C14 is introduced in the carboxyl group : 1. ΟΟ2 H, Ν—<ζ y~-Br _^HLL_U [(Li)2N—^ y~Li] 2. H2O > o- H N—<x />-C14OOH 2 PABA labeled with N15 has been synthesized by Lustig et al.11 by heating a solution of p-bromobenzoic acid in a sealed tube with N15-labeled am- monia. Br -<f V-COOH -J™L> Η 2Ν16<ζV-COOH B. PHYSICAL PROPERTIES PABA crystallizes in the form of monoclinic prisms which have a melting point of 186 to 187°.2'3> 12 Andrews and his coworkers13 reported a melting point of 188 to 188.5°. The molal heat capacity of the solid was determined to be 42.5 calories at 25° and 62.2 calories at the melting point, with a heat of crystallization of 5000 calories per mole.13 PABA is soluble in water, aqueous alcohol, methanol, isopropanol, bu- tanol, ether, glacial acetic acid, chloroform, and ethyl acetate; sparingly 4 W. L. Lewis and H. C. Cheetham, /. Am. Chem. Soc. 43, 2117 (1921). 5 J. Hirata, Japanese Pat. 109,708 (Feb. 21, 1935) [C.A. 29, 4776 (1935)]. 6 R. Adams, F. L. Cohen, and O. W. Rees, J. Am. Chem. Soc. 49, 1093 (1927). 7 P. H. Ravenscroft, R. W. Lesis, and O. W. Brown, Trans. Electrochem. Soc. 84, 145 (1943). 8 A. W. Hofmann, Ber. 9, 1299 (1876). 9F. Ullmann and J. B. Uzbachian, Ber. 36, 1797 (1903). 10 A. Murray, III, W. W. Foreman, and W. Langham, J. Am. Chem. Soc. 70, 1037 (1948). 11 B. Lustig, A. R. Goldfarb, and G. Gerstl, Arch. Biochem. 5, 59 (1944). 12 C. L. Lazzell and J. Johnston, /. Phys. Chem. 32, 1331 (1928). 13 D. H. Andrews, G. Lynn, and J. Johnston, J\ Am. Chem. Soc. 48, 1274 (1926).
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