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The Physical Chemistry of Cholanic Acids

  • Chapter
The Bile Acids Chemistry, Physiology, and Metabolism

Abstract

The conjugated bile acids are biologically the most important detergentlike molecules (1). They solubilize the insoluble components of bile, such as lecithin and cholesterol (2–9), aid in digestion by removing the products of pancreatic hydrolysis (monoglycerides and fatty acids) (10–12), and probably control certain intracellular events such as the synthesis of cholesterol in the intestinal mucosa (13). In certain cases, secondary bile salts may be toxic to cells and may cause cholestasis and hepatic necrosis (14–26). It is the belief of this author that the physicochemical characteristics of bile salts and their molecular interactions with other lipids, proteins, and complex carbohydrate molecules probably account for not only the physiological properties of bile salts but also the pathological conditions attributed to them.

Markle Scholar in Academic Medicine.

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References

  1. A.F. Hofmann and D.M. Small, Ann. Rev. Med. 18, 333 (1967).

    CAS  PubMed  Google Scholar 

  2. D.M. Small, M. Bourges, and D.G. Dervichian, Nature 211, 816 (1966).

    CAS  PubMed  Google Scholar 

  3. D.M. Small and M. Bourges, Mol. Crystals 1, 541 (1966).

    CAS  Google Scholar 

  4. D.M. Small, M. Bourges, and D.G. Dervichian, Biochim. Biophys. Acta 125, 563 (1966).

    CAS  PubMed  Google Scholar 

  5. M. Bourges, D.M. Small, and D.G. Dervichian, Biochim. Biophys. Acta 137, 157 (1967).

    CAS  PubMed  Google Scholar 

  6. M. Bourges, D.M. Small, and D.G. Dervichian, Biochim. Biophys. Acta 144, 189 (1967).

    CAS  PubMed  Google Scholar 

  7. D.M. Small, J. Lipid Res. 8, 551 (1967).

    Google Scholar 

  8. W.H. Admirand and D.M. Small, J. Clin. Invest. 47, 1043 (1968).

    CAS  PubMed  Google Scholar 

  9. D.M. Small, New Eng. J. Med. 277, 588 (1968).

    Google Scholar 

  10. D.M. Small, Advan. Intern. Med. 16, 243 (1970).

    Google Scholar 

  11. A.F. Hofmann, “The Function of Bile Salts in Fat Absorption,” Doctoral thesis, University of Lund, Sweden (1964).

    Google Scholar 

  12. A.F. Hofmann, Biochem. Biophys. Acta 70, 306 (1963).

    Google Scholar 

  13. A.F. Hofmann, Biochem. J. 89, 57 (1963).

    Google Scholar 

  14. J.M. Dietschy and M.D. Siperstein, J. Clin. Invest. 44, 1311 (1965).

    CAS  PubMed  Google Scholar 

  15. R.H. Palmer, Science 148, 1339 (1965).

    Google Scholar 

  16. R.H. Palmer and Z. Ruban, J. Clin. Invest. 45, 1255 (1966).

    CAS  PubMed  Google Scholar 

  17. F.G. Zaki, J.B. Carey, Jr., F.W. Hofbauer, and C. Nwokolo, J. Lab. Clin. Med. 69, 737 (1967).

    CAS  PubMed  Google Scholar 

  18. P. Holsti, Nature 186, 250 (1960).

    Google Scholar 

  19. A. Stalk, Experientia 16, 507 (1960).

    Google Scholar 

  20. R.D. Hunt, G.A. Leveille, and H.E. Sauberlich, Proc. Soc. Exp. Biol. Med. 113, 139 (1963).

    CAS  PubMed  Google Scholar 

  21. R.D. Hunt, G.A. Leveille, and H.E. Sauberlich, Proc. Soc. Exp. Biol. Med. 115, 277 (1964).

    CAS  PubMed  Google Scholar 

  22. G.A. Leveille, R.D. Hunt, and H.E. Sauberlich, Proc. Soc. Exp. Biol. Med. 115, 569 (1964).

    CAS  PubMed  Google Scholar 

  23. G.A. Leveille, R.D. Hunt, and H.E. Sauberlich, Proc. Soc. Exp. Biol. Med. 115, 573 (1964).

    CAS  PubMed  Google Scholar 

  24. G.A. Leveille, R.D. Hunt, and H.E. Sauberlich, Proc. Soc. Exp. Biol. Med. 116, 92 (1964).

    CAS  PubMed  Google Scholar 

  25. R.D. Hunt, Fed. Proc. 24, 431 (1965).

    Google Scholar 

  26. N.B. Javitt, Nature 210, 1262 (1966).

    Google Scholar 

  27. N.B. Javitt and S. Emerman, J. Clin. Invest. 47, 1002 (1968).

    CAS  PubMed  Google Scholar 

  28. Elsevier Encyclopedia of Organic Chemistry,“ pp. 167–214, Elsevier, Amsterdam (1940).

    Google Scholar 

  29. H. Sobotka, “Chemistry of Steroids,” Williams and Wilkins, Baltimore (1938).

    Google Scholar 

  30. G.A.D. Haslewood, Biol. Rev. Cambridge Phil. Soc. 39, 537 (1964).

    Google Scholar 

  31. G.A.D. Haslewood, in “Bile Salts” (R. Peters and F. G. Young, eds.), Methuen, London (1967).

    Google Scholar 

  32. G.A.D. Haslewood, Review, J. Lipid Res. 8, 535 (1967).

    CAS  PubMed  Google Scholar 

  33. G.A.D. Haslewood and V. Wootton, Biochem. J. 47, 584 (1950).

    CAS  PubMed  Google Scholar 

  34. H. Sobotka, “The Physiological Chemistry of the Bile,” Williams and Wilkins, Baltimore (1937).

    Google Scholar 

  35. B. Josephson, Physiol. Rev. 21, 463 (1943).

    Google Scholar 

  36. P. Ekwall, Acta Acad. Aboensis Math. Physica, 17, 3 (1951).

    Google Scholar 

  37. P. Ekwall, J. Coll. Sci., Suppl. 1, 66 (1954).

    Google Scholar 

  38. P. Ekwall, K. Fontell, and A. Sten, Proc. 2nd Intl. Cong. Surface Activity, Butterworth, London, p. 357 (1957).

    Google Scholar 

  39. K. Fontell, in “Surface Chemistry” (P. Ekwall, K. Groth, and v. Runnstrom-Reio, eds.), p. 252, Academic Press, New York (1965).

    Google Scholar 

  40. P. Ekwall, Intl. Conf. on Biochem. Probs. of Lipids, Koninkl. Vlaam. Acad. Wetenschap. Belgie. 103 (1953).

    Google Scholar 

  41. G. A. D. Haslewood, Physiol. Rev. 35, 178 (1955).

    Google Scholar 

  42. D.M. Small, Gastroenterology 52, 607 (1967).

    Google Scholar 

  43. D.M. Small, J. Am. Oil Chem. Soc. 45, 108 (1968).

    Google Scholar 

  44. D.M. Small, Advan. Chem. Ser. 84, 31 (1968).

    Google Scholar 

  45. M.C. Carey and D.M. Small, J. Coll. Interface Sci. 31, 382 (1969).

    CAS  Google Scholar 

  46. M.C. Carey and D.M. Small, Am. J. Med. 45, 590 (1970).

    Google Scholar 

  47. D.M. Small and W.H. Admirand, Nature 221, 265 (1969).

    CAS  PubMed  Google Scholar 

  48. A.F. Hofmann, Advan. Chem. Ser. 84, pp. 53–66 (1968).

    Google Scholar 

  49. D.M. Small, in “Bile Salt Metabolism” (L. Schiff, J. Carey, and J. Dietschy, eds.), Charles C Thomas, Springfield, Ill., Chap. 19 (1968).

    Google Scholar 

  50. L.J. Bellamy, “The Infrared Spectra of Complex Organic Molecules” ( 2nd ed. ), Wiley, New York (1958).

    Google Scholar 

  51. N.B. Colthup, L.H. Daly, and S.E. Wiberly, “Introduction to Infrared and Raman Spectroscopy,” Academic Press, New York, London (1964).

    Google Scholar 

  52. R.N. Jones and C. Sandorfy, in “Technique of Organic Chemistry” (A. Weissberger, ed.), p. 247, Interscience, New York (1956).

    Google Scholar 

  53. H.M. Randall, R.G. Fowler, N. Fuson, and J.R. Dangl, “Infrared Determination of Organic Structures,” D. Van Nostrand, Princeton, N.J. (1949).

    Google Scholar 

  54. R.M. Silverstein and G.C. Bassler, “Spectrometric Identification of Organic Compounds” ( 2nd ed. ), J. Wiley, New York (1967).

    Google Scholar 

  55. H.A. Szymanski, “IR Theory and Practice of Infrared Spectroscopy,” Plenum Press, New York (1964).

    Google Scholar 

  56. I.D.P. Wooten and H.S. Wiggins, Biochem. J. 55, 292 (1953).

    Google Scholar 

  57. G. Chihara, K. Matsuo, K. Arimoto, S. Sugano, K. Shimizu, and K. Mashimo, Chem. Phar. Bull. 9, 939 (1961).

    CAS  Google Scholar 

  58. G. Chihara, K. Matsuo, K. Arimoto, and S. Sugano, Chem. Pharm. Bull. 10, 1190 (1962).

    CAS  PubMed  Google Scholar 

  59. G. Chihara, K. Matsuo, A. Mizushima, E. Tanaka, K. Arimoto, and S. Sugano, Chem. Pharm. Bull. 10, 1184 (1962).

    CAS  PubMed  Google Scholar 

  60. T. Hoshita, S. Nagayoshi, and T. Kazuno, J. Biochem. 54, 369 (1963).

    CAS  PubMed  Google Scholar 

  61. T. Hoshita, S. Nagayoshi, M. Koughi, and T. Kazuno, J. Biochem. 56, 177 (1964).

    CAS  PubMed  Google Scholar 

  62. K. Dobriner, E.R. Katzenellenbogen, and R.N. Jones, “Infrared Absorption Spectra of Steroids,” Interscience, New York (1953).

    Google Scholar 

  63. L.M. Jackman, “Application of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry,” Pergamon Press, New York (1959).

    Google Scholar 

  64. J.A. Pople, W.G. Schneider, and H.J. Bernstein, “High-Resolution Nuclear Magnetic Resonance,” McGraw-Hill, New York (1959).

    Google Scholar 

  65. O. Jarketzky and C.D. Jarketzky, in “Methods of Biochemical Analysis,” Vol. IX, Interscience, New York (1962).

    Google Scholar 

  66. N.S. Bhacca and D.H. Williams, “Applications of NMR Spectroscopy in Organic Chemistry,” Holden-Day, San Francisco (1964).

    Google Scholar 

  67. D. Chapman and P.D. Magnus, “Introduction to Practical High Resolution Nuclear Magnetic Resonance Spectroscopy,” Academic Press, London (1966).

    Google Scholar 

  68. J.W. Emsley, J. Feeney, and L.H. Sutcliffe, “High Resolution Nuclear Magnetic Resonance Spectroscopy,” Vol. I, Pergamon Press, New York (1965), Vol. I I (1966).

    Google Scholar 

  69. D.M. Small, S.A. Penkett, and D. Chapman, Biochim. Biophys. Acta 176, 178 (1969).

    CAS  PubMed  Google Scholar 

  70. J.N. Shoolery and M.T. Rogers, J. Am. Chem. Soc. 80, 5121 (1958).

    CAS  Google Scholar 

  71. D. Lavie, S. Greenfield, Y. Kashman, and E. Glotter, Israel J. Chem. 5, 151 (1967).

    CAS  Google Scholar 

  72. P. Eneroth, B. Gordon, R. Ryhage, and J. Sjövall, J. Lipid Res. 7, 511 (1966).

    CAS  PubMed  Google Scholar 

  73. P. Eneroth, B. Gordon, and J. Sjövall, J. Lipid Res. 7, 524 (1966).

    CAS  PubMed  Google Scholar 

  74. A. Norton and B. Haner, Acta Cryst. 19, 477 (1965).

    CAS  Google Scholar 

  75. T.C. Laurent and H. Persson, Biochim. Biophys. Acta 106, 616 (1965).

    CAS  PubMed  Google Scholar 

  76. The Merck Index,“ 7th ed. (P.G. Stecher, ed.), Merck and Co., Rahway, New Jersey (1960).

    Google Scholar 

  77. B. Josephson, Biochem. J. 29, 1484 (1935a).

    CAS  PubMed  Google Scholar 

  78. Y. Go and O. Kratky, Z. Physik. B26, 439 (1934).

    Google Scholar 

  79. O. Kratky and G. Giacomello, Monatsh. 69, 427 (1936).

    CAS  Google Scholar 

  80. V. Caglioti and G. Giacomello, Gazz. Chem. Ital. 69, 245 (1939).

    CAS  Google Scholar 

  81. G. Giacomello and M. Romeo, Gazz. Chem. Ital. 73, 285 (1943).

    CAS  Google Scholar 

  82. H. Wieland and H. Sorge, Z. Physical Chem. 97, 1 (1916).

    CAS  Google Scholar 

  83. G. Giacomello and O. Kratky, Z. Kristallograph. 95, 459 (1936).

    CAS  Google Scholar 

  84. J. Parsons, W.T. Beher, and G.D. Baker, Henry Ford Hosp. Med. Bull. 6, pt. II, 365 (1958).

    Google Scholar 

  85. J. Parsons, W.T. Beher, and G.D. Baker, Henry Ford Hosp. Med. Bull. 9, 54 (1961).

    CAS  PubMed  Google Scholar 

  86. J. Parsons, S.T. Wong, W.T. Beher, and G.D. Baker, Henry Ford Hosp. Med. Bull. 11, 23 (1963).

    CAS  Google Scholar 

  87. J. Parsons, S.T. Wong, W.T. Beher, and G.D. Baker, Henry Ford Hosp. Med. Bull. 12, 87 (1964).

    CAS  PubMed  Google Scholar 

  88. N.K. Adam, “The Physics and Chemistry of Surfaces,” 3rd ed. (H. Milford, ed.), Oxford Univ. Press, London (1941).

    Google Scholar 

  89. G.L. Gaines, Jr., “Insoluble Monolayers at Liquid-Gas Interfaces,” Wiley, Inter-science, New York (1966).

    Google Scholar 

  90. A.W. Adamson, “The Physical Chemistry of Surfaces,” Interscience, New York (1960).

    Google Scholar 

  91. W.D. Harkins, “The Physical Chemistry of Surface Films,” Reinhold, New York (1952).

    Google Scholar 

  92. J.T. Davies and E.K. Rideal, “Interfacial Phenomena,” Academic Press, New York (1961).

    Google Scholar 

  93. I. Langmuir, J. Am. Chem. Soc. 39, 1848 (1917)

    Google Scholar 

  94. D.G. Dervichian, “La Technique des Couches Superficielles,” Chap. XIII, Techniques de Laboritoire, Masson, Paris (1954).

    Google Scholar 

  95. J.W. Gibbs, Collected Works, Vol. 1, 1931, New York (1876).

    Google Scholar 

  96. D.J. Crisp, in “Surface Chemistry,” p. 17, Butterworths, London (1949).

    Google Scholar 

  97. E. Otero Aenlle and R.C. Carro, Anales Fisica Quimica 52, 85 (1959).

    Google Scholar 

  98. D.G. Dervichian, Comptes Rendus de la 2e Réunion de Chimie Physique, Paris, p. 443, June (1952).

    Google Scholar 

  99. D.G. Dervichian, in “Progress in Chemistry of Fats and Other Lipids,” Vol. 2, p. 193, Pergamon Press, London (1954).

    Google Scholar 

  100. D.G. Dervichian and M. Joly, Nature 141, 975 (1938).

    Google Scholar 

  101. D.G. Dervichian, J. Phys. 7, 427 (1935).

    Google Scholar 

  102. N.L. Gershfeld, “Cohesive forces in monomolecular films at an air-water interface,” Advan. Chem. Ser. 84, 115 (1958).

    Google Scholar 

  103. H.E. Ries, Jr., Sci. Am. March, 2 (1961).

    Google Scholar 

  104. P. Ekwall and R. Ekholm, Proceedings of the International Congress on Surface Activity, 2nd ed., London, 1957, p. 23, Butterworths, London (1957).

    Google Scholar 

  105. P. Ekwall, R. Ekholm, and A. Norman, Acta Chem. Scand. 11, 693 (1957).

    CAS  Google Scholar 

  106. P. Ekwall, R. Ekholm, and A. Norman, Acta Chem. Scand. 11, 703 (1957).

    CAS  Google Scholar 

  107. P. Ekwall, R. Silander, and J. Rydberg, 3rd International Congress Surface Activity, Cologne, Vol. II, B, p. 703 (1960).

    Google Scholar 

  108. E. Otero Aenlle, Proceedings of the International Congress on Surface Activity, London, 2nd ed., I, p. 135, Butterworths, London (1957).

    Google Scholar 

  109. E. Otero Aenlle and R.C. Carro, Estos Anales B51, 515 (1955).

    Google Scholar 

  110. S.G. Fernandez, A.L. Lopez, and E. Otero Aenlle, Anales Fisica Quimica B60 137 (1964).

    CAS  Google Scholar 

  111. A.L. Lopez, S.G. Fernandez, and E. Otero Aenlle, Koll. Zeit. 211, 131 (1966).

    CAS  Google Scholar 

  112. J.M. Trillo, S.G. Fernandez, and P.S. Pedero, Anales Fisica Quimica B63, 933 (1967).

    Google Scholar 

  113. J. H. Shulman and E.K. Rideal, Proc. Roy. Soc. B112, 29 (1937).

    Google Scholar 

  114. K.D. Dreher, J.H. Schulman, and A.F. Hofmann, J. Coll. Interf. Sci. 25, 71 (1967).

    Google Scholar 

  115. P. Desnuelle, J. Molines, and D.G. Dervichian, Bull. Soc. Cham. France 18, 197 (1951).

    Google Scholar 

  116. L. de Bernard and D.G. Dervichian, Bull. Soc. Chim. Biol. 37, 843 (1955).

    Google Scholar 

  117. L. de Bernard, Bull. Soc. Chim. Biol. 40, 161 (1958).

    Google Scholar 

  118. J.B. Leathes, Lancet 1, 853 (1925).

    Google Scholar 

  119. G.H.A. Clowes, in “Surface Chemistry, ” Publ. of Am. Assoc. for Advancement of Science, No. 21, 1 (1943).

    Google Scholar 

  120. D.M. Small, unpublished data.

    Google Scholar 

  121. D.J. Crisp, in “Surface Chemistry,” p. 23, Butterworths, London (1949).

    Google Scholar 

  122. J.P. Kratohvil and H.T. Dellicolli, Can. J. Biochem. 46, 945 (1968).

    CAS  PubMed  Google Scholar 

  123. P. Ekwall, T. Rosendahl, and A. Sten, Acta Chem. Scand. 12, 1622 (1958).

    CAS  Google Scholar 

  124. W.S. Bennett, G. Eglinton, and S. Kovac, Nature 217, 776 (1967).

    Google Scholar 

  125. P. Ekwall, T. Rosendahl, and N. Lofman, Acta Chem. Scand. 11, 590 (1957).

    CAS  Google Scholar 

  126. E. Back and B. Steenberg, Acta Chem. Scand. 4, 810 (1950).

    CAS  Google Scholar 

  127. H. Hammarsten, Biochem. Z. 481 (1924).

    Google Scholar 

  128. B.A. Josephson, Biochem. Z. 263, 428 (1933).

    Google Scholar 

  129. P. Ekwall, E.V. Lindstrom, and K. Setala, Acta Chem. Scand. 5, 990 (1951).

    CAS  Google Scholar 

  130. R.H. Dowling and D.M. Small, Gastroenterology 54, 1291 (abstract) (1968).

    Google Scholar 

  131. R.H. Palmer, P.B. Glickman, and A. Kappas, J. Clin. Invest. 41, 1573 (1962).

    CAS  PubMed  Google Scholar 

  132. J.B. Carey, Jr., and G. Williams, Science 150, 620 (1965).

    CAS  PubMed  Google Scholar 

  133. W.H. Admirand and C. Trey, Clin. Res. 16, 278 (1968).

    Google Scholar 

  134. M.J. Schick, “Nonionic Surfactants,” Marcel Dekker, New York (1967).

    Google Scholar 

  135. F. Krafft and H. Wiglow, Ber. 28, 2566 (1895).

    CAS  Google Scholar 

  136. F. Lachampt and R. Perron, Traite Chim. Organ. 22, 837 (1953).

    Google Scholar 

  137. M. Demarc and D.G. Dervichian, Bull. Soc. Chim. France 12, 939 (1945).

    Google Scholar 

  138. R.H. Palmer, Proc. U.S. Nat. Acad. Sci. 58, 1047 (1967).

    Google Scholar 

  139. M. Raison, Proc. Intern. Cong. Surface Activity, London, 2nd ed., p. 374, Butter-worths, London (1957).

    Google Scholar 

  140. H. Lecuyer and D.G. Dervichian, Kolloid Z. 197, 115 (1964).

    CAS  Google Scholar 

  141. D. Rudman and F.E. Kendall, J. Clin. Invest. 36, 538 (1957).

    CAS  PubMed  Google Scholar 

  142. R.T. Reinke and J.D. Wilson, Clin. Res. 15, 34 (1967).

    Google Scholar 

  143. K. Shinoda, T. Nakagawa, B. Tamamushi, and T. Isemura, “Colloidal Surfactants,” Acadmic Press, New York (1963).

    Google Scholar 

  144. P. Ekwall, K. Fontell, and A. Sten, Proc. Intern. Cong. Surface Activity, London, p. 357, Butterworths, London (1957).

    Google Scholar 

  145. A. Norman, Acta Chem. Scand. 14, 1295 (1960).

    CAS  Google Scholar 

  146. P. DeMoerloose and R. Ruyssen, J. Pharm. Belg. 14, 95 (1959).

    CAS  Google Scholar 

  147. T. Furusawa, Fukuoka Acta Med. 53, 124 (1962).

    CAS  PubMed  Google Scholar 

  148. H. Miyake, T. Murakoshi, and T. Hisatsugu, Fukuoka Igaku Zassi 53, 659 (1962).

    Google Scholar 

  149. T. Bates, M. Gibaldi, and J.L. Konig, Nature 210, 1331 (1966).

    CAS  PubMed  Google Scholar 

  150. T.R. Bates, Doctoral thesis, Columbia University, New York (1966).

    Google Scholar 

  151. M.C. Carey, D. Chapman, M.D. Barratt, and D.M. Small, unpublished data.

    Google Scholar 

  152. M.C. Carey, D. Chapman, C.J. Hart, and D.M. Small, unpublished data.

    Google Scholar 

  153. S.A. Johnston and J.W. McBain, Proc. Roy. Soc. London, Ser. A 181, 119 (1943).

    Google Scholar 

  154. D.M. Small, unpublished observations on the surface tension of bile salt solutions by the Willhelmy plate method.

    Google Scholar 

  155. F.P. Woodford, J. Lipid Res. 10, 539 (1969).

    CAS  PubMed  Google Scholar 

  156. G. Nemethy and H.A. Scheraga, J. Phys. Chem. 66, 1773 (1962).

    CAS  Google Scholar 

  157. P. Mukerjee, Adv. Colloid Interface Sci. 1, 241 (1967).

    CAS  Google Scholar 

  158. B.D. Flockhart, J. Colloid Sci. 16, 484 (1961).

    Google Scholar 

  159. E.D. Goddard and G.C. Benson, Can. J. Chem. 35, 986 (1957).

    CAS  Google Scholar 

  160. M.J. Schick, S.M. Atlas, and F.R. Eirich, J. Phys. Chem. 66, 1326 (1962).

    CAS  Google Scholar 

  161. M.J. Schick, J. Phys. Chem. 68, 3584 (1964).

    Google Scholar 

  162. M.J. Schick, J. Colloid Sci. 17, 801 (1962).

    Google Scholar 

  163. P. Mukerjee, J. Phys. Chem. 66, 1375 (1962).

    CAS  Google Scholar 

  164. G. Stainsby and A.E. Alexander, Trans. Faraday Soc. 46, 587 (1950).

    CAS  Google Scholar 

  165. J. Ti. G. Overbeek and D. Stigter, Rec. Tray. Chim. 755, 1263 (1956).

    Google Scholar 

  166. H.S. Frank and M.W. Evans, J. Chem. Phys. 13, 507 (1945).

    CAS  Google Scholar 

  167. J.D. Bernal, “The State and Movement of Water in Living Organisms,” p. 7ff, Cambridge University Press, London (1964).

    Google Scholar 

  168. : F. Franks, Chem. Ind. 1968, 560 (May 4, 1968 ).

    Google Scholar 

  169. J.A. Olson and J.S. Herron, Proc. Intern. Cong. Biochem. 6th, New York, 1964, pp. 7, 112 (abstract) (1964).

    Google Scholar 

  170. J. Herron and J.A. Olson, personal communication.

    Google Scholar 

  171. B. Borgstrom, Biochim. Biophys. Acta 106, 171 (1965).

    CAS  PubMed  Google Scholar 

  172. H. Sobotka and N. Czeczowczka, J. Colloid Sci. 13, 188 (1958).

    CAS  Google Scholar 

  173. A. Rich and D.M. Blow, Nature 182, 423 (1958).

    CAS  PubMed  Google Scholar 

  174. D.M. Blow and A. Rich, J. Am. Chem. Soc. 82, 3566 (1960).

    CAS  Google Scholar 

  175. M.J. Schick, J. Am. Oil Chem. Soc. 40, 680 (1963).

    Google Scholar 

  176. M.F. Emerson and A. Holtzer, J. Phys. Chem. 71, 3320 (1967).

    CAS  PubMed  Google Scholar 

  177. J. Clifford, Trans. Faraday Soc. 60, 276 (1964).

    Google Scholar 

  178. P. Ekwall, K. Setala, and L. Sjoblom, Acta Chem. Scand. 5, 175 (1951).

    CAS  Google Scholar 

  179. M.C. Carey and D.M. Small, Gastroenterology 58, 1057 (1970).

    Google Scholar 

  180. D.B. Neiderhiser and H.P. Roth, Proc. Soc. Exp. Biol. Med. 128, 221 (1968).

    CAS  PubMed  Google Scholar 

  181. D.B. Neiderhiser and H.P. Roth, personal communication.

    Google Scholar 

  182. A.N. Campbell and N. O. Findlay Smith, “The Phase Rule,” 9th ed., Dover, New York (1951).

    Google Scholar 

  183. G. Masing, “Ternary Systems,” Dover, New York (1944).

    Google Scholar 

  184. S. Glasstone and D. Lewis, “Elements of Physical Chemistry,” 2nd ed., Macmillan London (1963).

    Google Scholar 

  185. R.D. Vold and J.W. McBain, J. Am. Chem. Soc. 63, 1296 (1941).

    CAS  Google Scholar 

  186. D.M. Small, in “Surface Chemistry of Biological Systems” (M. Blank, ed.), Plenum Press, New York p. 55 (1970).

    Google Scholar 

  187. D. G. Dervichian, in “Progress in Biophysics and Molecular Biology” (J. Butler and H. Huxley, eds.), Ch. 14, Academic Press, New York (1964).

    Google Scholar 

  188. F. Rosevear, J. Am. Oil Chem. Soc. 31, 628 (1954).

    CAS  Google Scholar 

  189. F. Husson, H. Mustacchi, and V. Luzzati, Acta Crystal. 13, 668 (1960).

    CAS  Google Scholar 

  190. V. Luzzati and F. Husson, J. Cell. Biol. 12, 297 (1962).

    Google Scholar 

  191. K.D. Lawson and T.J. Flautt, Mol. Crystals 1, 241 (1966).

    CAS  Google Scholar 

  192. T.J. Flautt and K.D. Lawson, Adv. Chem. Series 63, 26 (1965).

    Google Scholar 

  193. D. Chapman, P. Byrne, and G.G. Shipley, Proc. Trans. Faraday Soc. 290, 115 (1966).

    CAS  Google Scholar 

  194. D. Chapman, R.M. Williams, and B.D. Ladbrooke, Chem. P/tys. Lipids 1, 445 (1967).

    CAS  Google Scholar 

  195. D. Chapman and N.J. Salsbury, Trans. Faraday Soc. 62, 2607 (1966).

    CAS  Google Scholar 

  196. N.J. Salsbury and D. Chapman, Biochim. Biophys. Acta 163, 314 (1968).

    CAS  PubMed  Google Scholar 

  197. S.A. Penkett, A.G. Flook, and D. Chapman, Chem. Phys. Lipids 2, 273 (1968).

    CAS  Google Scholar 

  198. D. Champman, Adv. Chem. Ser. 63, 157 (1967).

    Google Scholar 

  199. D.M. Small and S. Rapo, New Eng. J. Med. 283, 53 (1970).

    CAS  PubMed  Google Scholar 

  200. J.W. McBain, R.D. Vold, and R. Porter, Ltd. Eng. Chem. 33, 1049 (1941).

    CAS  Google Scholar 

  201. B. Borgstrom, J. Lipid Res. 8, 598 (1967).

    CAS  PubMed  Google Scholar 

  202. E.B. Feldman and B. Borgstrom, Bioehim. Biophys. Acta 125, 136 (1966).

    CAS  Google Scholar 

  203. E.B. Feldman and B. Borgstrom, Lipids 1, 430 (1966).

    CAS  PubMed  Google Scholar 

  204. G. Benzonana, Biochim. Biophys. Acta 176, 836 (1969).

    CAS  PubMed  Google Scholar 

  205. D.M. Small, Fed. Proc. 29, 1320 (1970).

    Google Scholar 

  206. G. Friedel, Ann. Physique 17, 273 (1922).

    Google Scholar 

  207. G.H. Brown and W.G. Shaw, Chem. Rev. 56, 1049 (1957).

    Google Scholar 

  208. G.W. Gray, “Molecular Structure and the Properties of Liquid Crystals,” p. 114, Academic Press, New York (1962).

    Google Scholar 

  209. J. H. Hildebrand and R.L. Scott, “The Solubility of Nonelectrolytes,” Dover, New York (1964).

    Google Scholar 

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Authors and Affiliations

  1. Section of Biophysics Department of Medicine, Boston University School of Medicine, USA

    Donald M. Small

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  1. Donald M. Small
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  1. Biochemistry Research Division Department of Medicine, Sinai Hospital of Baltimore, Inc., Baltimore, Maryland, USA

    Padmanabhan P. Nair

  2. The Wistar Institute, Philadelphia, Pennsylvania, USA

    David Kritchevsky

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© 1971 Springer Science+Business Media New York

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Small, D.M. (1971). The Physical Chemistry of Cholanic Acids. In: Nair, P.P., Kritchevsky, D. (eds) The Bile Acids Chemistry, Physiology, and Metabolism. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-0647-5_8

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  • DOI: https://doi.org/10.1007/978-1-4757-0647-5_8

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