Skip to main content

Advertisement

SpringerLink
Log in

The contribution of professor Paul Karrer (1889–1971) to dextrins

  • Review Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

Paul Karrer (1889–1971), a Swiss organic chemist best known for his research on vitamins, has published more than 1000 articles. In 1919, Karrer became professor of chemistry at the University of Zurich and in the same year he was appointed director of the Chemical Institute in Zurich, where he remained until his retirement in 1959. Karrer’s most famous work was on vitamins, and probably his most important contribution was his demonstration in 1931 that vitamin A was structurally related to carotenoid. Karrer also published important works on natural products, carotenoids and other plant pigments, coenzymes, alkaloids, amino acids, sugars, carbohydrates, polysaccharides, and organometallic compounds. Professor Karrer was awarded the Nobel Prize in chemistry in 1937 for his research into the constitution of carotenoids, flavins and vitamins A and B2, a prize shared with the British chemist Sir Walter Norman Haworth. However, few researchers working in the field of cyclodextrins know that Karrer was also one of the first to take an interest in these molecules. Between 1920 and 1925, he published several studies on the nomenclature, structure and chemistry of dextrin-α and dextrin-β. This historical review, on the occasion of the fiftieth anniversary of his death, aims, on the one hand, to retrace his immense scientific career highlighting selected works on vitamins and alkaloids and, on the other hand, to commemorate his contribution to (cyclo)dextrin chemistry.

Graphic abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. French, D.: The Schardinger dextrins. In: Advances in Carbohydrate Chemistry. Wolfrom M.L. (ed), New York: Academic Press Inc., vol. 12, pp. 189–260 (1957)

  2. Bender, M.L., Komiyama, M.: Cyclodextrin chemistry. Reactivity and structure: Concepts in organic chemistry. Berlin: Springer-Verlag (1978)

  3. Szejtli, J.: Cyclodextrins and their inclusion complexes. Akadémiai Kiadó, Budapest (1982)

    Google Scholar 

  4. Kainuma, K.: Starch oligosaccharides: Linear, branched, and cyclic, In: Starch - Chemistry and technology, 2nd edition. London: Academic Press Ltd., Whistler R.L., BeMiller J.N. and Paschall E.F. (eds), chapter V, 1984, pp. 125–152 (1984)

  5. Atwood, J.L., Davies, J.E.D., MacNicol, D.D.: Inclusion compounds. Oxford University Press, London (1984)

    Google Scholar 

  6. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743–1753 (1998)

    Article  CAS  PubMed  Google Scholar 

  7. Bilensoy, E.: Cyclodextrins in pharmaceutics, cosmetics and biomedicine. John Wiley & Sons Inc, Current and future industrial applications, Hoboken (2011)

    Book  Google Scholar 

  8. Crini, G.: Review: a history of cyclodextrins. Chem. Rev. 14, 10940–10975 (2014)

    Article  Google Scholar 

  9. Morin-Crini, N., Fourmentin, S., Crini, G. (eds).: Cyclodextrines. Besançon: Presses Universitaires de Franche-Comté, France (2015)

  10. Crini, G., Fourmentin, S., Fenyvesi, É., Torri, G., Fourmentin, M., Morin-Crini, N.: Cyclodextrins, from molecules to applications. Environ. Chem. Lett. 16, 1361–1375 (2018)

    Article  CAS  Google Scholar 

  11. Jansook, P., Ogawa, N., Loftsson, T.: Cyclodextrins: Structure, physicochemical properties and pharmaceutical applications. Int. J. Pharma. 535, 272–284 (2018)

    Article  CAS  Google Scholar 

  12. Villiers, A.: Sur la transformation de la fécule en dextrine par le ferment butyrique. Chimie Organique - Compte Rendus des Séances de l’Académie des Sciences (France) Février, CXII, 435–437 (1891)

  13. Villiers, A.: Sur la fermentation de la fécule par l’action du ferment butyrique., Chimie Organique - Compte Rendus des Séances de l’Académie des Sciences (France) Juin, CXII, 536–538 (1891)

  14. Schardinger, F.: Über thermophile bakterien aus verschiedenen speisen und milch, sowie über einige umsetzungsprodukte derselben in kohlenhydrathaltigen nährlösungen, darunter krystallisierte polysaccharide (dextrine) aus stärke. Z. Unters. Nahr. Genussm. 6, 865–880 (1903)

    CAS  Google Scholar 

  15. Schardinger, F.: Bacillus macerans, ein aceton bildender Rottebacillus. Zentralbl. Bakteriolo Parasitenkd. Infektionskrankh. 14, 772–781 (1905)

    CAS  Google Scholar 

  16. Schardinger, F.: Zur biochemie des Bacillus macerans. Zentralbl. Bakteriol. Parasitenkd. Infektionskrankh. 19, 161–163 (1907)

    Google Scholar 

  17. Schardinger, F.: Ueber die bildung kristallisierter fehlingsche lösung nicht reduzierender körper (polysaccharide) aus stärke durch mikrobielle tätigkeit. Zentralbl. Bakteriol. Parasitenkd. Infektionskrankh. 22, 98–103 (1909)

    CAS  Google Scholar 

  18. Schardinger, F.: Bildung kristallisierter polysaccharide (dextrine) aus stärkekleister durch mikrobien. Zentralbl. Bakteriol. Parasitenkd. Infektionskrankh. 29, 188–197 (1911)

    Google Scholar 

  19. Crini, G.: The contribution of Franz Schardinger to cyclodextrins: a tribute on the occasion of the centenary of his death. J. Incl. Phenom. Macrocyclic Chem. 97, 19–28 (2020)

    Article  CAS  Google Scholar 

  20. Szejtli, J.: Cyclodextrin technology. Kluwer Academic Publishers, Dordrecht (1988)

    Book  Google Scholar 

  21. 21Robyt, J.F.: Cyclodextrins. In: essentials of carbohydrate of chemistry. New York: Springer-Verlag Inc., chapter 8, pp. 245–261 (1998)

  22. Loftsson, T., Duchêne, D.: Cyclodextrins and their pharmaceutical applications: historical perspectives. Int. J. Pharm. 329, 1–11 (2007)

    Article  CAS  PubMed  Google Scholar 

  23. Caesar, G.V.: The Schardinger dextrins. In: starch and its derivatives. Radley JA (ed), London: Chapman and Hall Ltd., EC4, fourth edition, chapter X, pp. 290–305 (1968)

  24. Thoma, J.A., Stewart, L.: Cycloamyloses. In: starch, chemistry and technology. Whistler R.L. and Paschall E.F. (eds), New York: Academic Press, volume 1: fundamental aspects, chapter IX, pp. 209–249 (1965)

  25. Karrer, P.: Zur Kenntnis der Polysaccharide. I. Methylierung der Stärke. Helv. Chim. Acta 3, 620–625 (1920)

  26. Karrer, P., Nägeli, C.: Polysaccharide II. Zur Konstitution der Diamylose. Helv. Chim. Acta 4, 169–173 (1921)

  27. Karrer, P., Nägeli, C. Zur Kenntnis der Polysaccharide IV. Über den aufbau der Kartofeelstärke. Helv. Chim. Acta 4, 185–202 (1921)

  28. Karrer, P., Nägeli, C.: Polysaccharide VI. Die Konstitution der Stärke und des Glykogens. Helv. Chim. Acta 4, 263–269 (1921)

  29. Karrer, P., Nägeli, C., Hurwitz, O., Wälti, A.: Polysaccharide VIII. Zur Kenntnis der Stärke und der Amylosen. Helv. Chim. Acta 4, 678–699 (1921)

  30. Karrer, P.: Polysaccharide XI. Die Verbindungen der Anhydrozucker mit Alkalilaugen. Eine Methode zur Bestimmung der Grundkörper polymerer Anhydrozucker. Helv. Chim. Acta 4, 811–816 (1921)

  31. Karrer, P.: Untersuchungen über polymere kohlenhydrate. Angew. Chem. 5, 85–90 (1922)

    Article  Google Scholar 

  32. Karrer, P., Staub, M., Wälti, A.: Polysaccharide XIII: Zur Kenntnis des Inulins und der Alkalihydroxydverbindungen der Anhydrozucker. Helv. Chim. Acta. 1, 129–139 (1922)

    Article  Google Scholar 

  33. Karrer, P., Bürkin, E.: Polysaccharide XIV. Zur Kenntnis der Amylosen. Helv. Chim. Acta. 5,181–187 (1922)

  34. Karrer, P., Smirnoff, AP.: Polysaccharide XV. Die Konstitution der Diamylose und des der Cellulose zu Grunde liegenden Anhydrozuckers (Cellosan). Helv. Chim. Acta 5, 187–201 (1922)

  35. Karrer, P., Rosenberg, J.O.: Über Sublimationsversuche mit Kohlenhydraten. Helv. Chim. Acta 5, 575–576 (1922)

    Article  CAS  Google Scholar 

  36. Karrer, P., Fioroni, W.: Polysaccharide XIX. Die Verbrennungswärmen der Kohlenhydrate. Helv. Chim. Acta 6, 396–401 (1923)

    Article  CAS  Google Scholar 

  37. Karrer, P.: Polysaccharides XX. Zur Kenntniss polymerer Kohlenhydrate. Helv. Chim. Acta 6, 402–409 (1923)

    Article  CAS  Google Scholar 

  38. Karrer, P.: Polymere Kohlenhydrate. Akademische Verlagsgesellschaft, Leipzig (1925)

    Google Scholar 

  39. Stoll, A.: Aus der Chemie der Naturstoffe (First Paul Karrer Lecture). Experientia 16, 85–100 (1960)

    Article  CAS  PubMed  Google Scholar 

  40. Eugster, C.H.: Das Portrait: Paul Karrer 1889–1971. Chem. unserer Zeit 6, 147–153 (1972)

    Article  CAS  Google Scholar 

  41. Roche, J.: Eloge - Paul Karrer (1889–1971). Bull. Acad. Nat. Med. Paris 156, 89–92 (1972)

    CAS  PubMed  Google Scholar 

  42. Schmid, H.: Paul Karrer, 1889–1971. Bull. Schweizerischen Akademie Medizinischen Wissenschaften 28, 367–370 (1972)

    CAS  Google Scholar 

  43. Wettstein, A.: Paul Karrer 1889–1971. Helv. Chim. Acta 55, 313–328 (1972)

    Article  CAS  Google Scholar 

  44. Beer, FJ.: Le professeur Paul Karrer et la liberté de la science, Société Française d’Histoire de la Médicine, séance du 23 avril 1977, 221–231 (1977)

  45. Isler, O.: Paul Karrer, 21 April 1889–18 June 1971. Biographical Memoirs of Fellows of the Royal Society, Royal Society (Great Britain) 24, 245–321 (1978)

  46. James, L.K.: Paul Karrer, Nobel laureates in chemistry 1901–1992. History of Modern Sciences. American Chemical Society, Library of Congress Cataloging in Publication Data, CHF, pp. 242–247 (1993)

  47. Oesper, R.E.: Paul Karrer. J. Chem Educat 23, 392–392 (1946)

    Article  CAS  Google Scholar 

  48. Dahn, H., Cherbuliez, E., Chekhitliez, E.: Professor Dr. Paul Karrer zum 80,. Geburtstag. Helv. Chim. Acta 52, 568A-568C (1969)

  49. Karrer, P.: Zur Kenntnis aromatischer Arsenverbindungen I. Über p-Nitroso-phenylarsinsäure. Ber. Dtsch. Chem. Ges. 45, 2065–2068 (1912)

    Article  CAS  Google Scholar 

  50. Francis, G.W., Upadhyay, R.R., Liaaen-Jensen, S., Karrer, P.: Structure of the acetylenic dehydrogenation product of canthaxanthin. Acta Chem. Scand. 24, 3053–3055 (1970)

    Article  CAS  Google Scholar 

  51. Werner, A., Karrer, P.: Über Nitroso-pentamminkobaltisalze. Helv. Chim. Acta 1, 54–78 (1918)

    Article  CAS  Google Scholar 

  52. Karrer, P.: Glucoside VI. Beitrag zur Konstitution und Konfiguration der Glucoside. Helv. Chim. Acta 3, 258–260 (1920)

    Article  CAS  Google Scholar 

  53. Karrer, P., Baumgarten, R., Günther, S., Harder, W., Lang, L.: Zur Kenntnis der Glucoside IX. Helv. Chim. Acta 4, 130–148 (1921)

    Article  CAS  Google Scholar 

  54. Karrer, P., Widmer, F.: Polysaccharide III. Beitrag zur Kenntnis der Cellulose. Helv. Chim. Acta 4, 174–184 (1921)

    Article  CAS  Google Scholar 

  55. Karrer, P., Lang, L.: Polysaccharide V. Die Methylierung des Inulins. Helv. Chim. Acta 4, 249–256 (1921)

    Article  CAS  Google Scholar 

  56. Karrer, P., Smirnoff, A.P.: Polysaccharide XVII. Beitrag zur kenntnis des chitins, Helv. Chim. Acta 5, 832–852 (1922)

  57. Karrer, P., Joos, B.: Polysaccharide XVIII. Das Lichenin. Biochem. Z. 136, 537–541 (1922)

    Google Scholar 

  58. Karrer, P.: Neuere Anschauungen liber den Aufbau der polymeren Kohlenhydrate. Dtsch. Med. Wschr. 49, 1074–1075 (1923)

    Article  Google Scholar 

  59. Karrer, P., Schnider, O., Smirnoff, A.P.: Polysaccharide XXIX. Zur kenntnis des chitins II und konfiguration des glucosamins. Helv. Chim. Acta 7, 1039–1045 (1924)

    Article  CAS  Google Scholar 

  60. Karrer, P., Widmer, F.: Polysaccharide IX. Zur Kenntnis der Cellulose und des Lignins. Helv. Chim. Acta 4, 700–702 (1921)

    Article  CAS  Google Scholar 

  61. Karrer, P., Salomon, H.: Ueber zwei neue Alkaloide aus der Yohimberinde. Helv. Chim. Acta 9, 1059–1062 (1925)

    Article  Google Scholar 

  62. Karrer, P.: Sur les matières colorantes. Bull. Soc. Chim. France 43, 1041–1058 (1928)

    CAS  Google Scholar 

  63. Karrer, P., Salomon, H.: Ueber Pflanzenfarbstoffe III. Zur Kenntnis der Safranfarbstoffe I. Helv. Chim. Acta 10, 397–440 (1927)

    Article  CAS  Google Scholar 

  64. Euler, H.V., Karrer, P.: Zur Kenntnis hochkonzentrierter Vitamin-A-Präparate. Helv. Chim. Acta 14, 1040–1044 (1931)

    Article  Google Scholar 

  65. Karrer, P., Morf, R., Schoepp, K.: Zur Kenntnis des Vitamins-A aus Fischtranen II. Helv. Chim. Acta 14, 1431–1436 (1931)

    Article  CAS  Google Scholar 

  66. Karrer, P., Helfenstein, A.: Pflanzenfarbstoffe XVII. Ueber die Natur der Carotinoide im Schaf- und Kuhkot. Helv. Chim. Acta 13, 86–87 (1930)

    Article  CAS  Google Scholar 

  67. Karrer, P.: Carotinoide. Physiologie 34, 812–847 (1932)

    CAS  Google Scholar 

  68. Karrer, P., Helfenstein, A.: Plant pigments. Ann. Rev. Biochem. 2, 397–418 (1933)

    CAS  Google Scholar 

  69. Karrer, P.: Ueber vitamine. Vierteljahresschr. Zürcher Naturforsch. Ges. 77, 83–98 (1932)

    CAS  Google Scholar 

  70. Karrer, P., Salomon, H., Schoepp, K., Morf, R.: Zur Kenntnis des antiskorbutischen Vitamins (Vitamin C). Helv. Chim. Acta 16, 181–183 (1933)

    Article  CAS  Google Scholar 

  71. Karrer, P., Schwarzenbach, G., Schoepp, K.: Ueber Vitamin C. Helv. Chim. Acta 16, 302–306 (1933)

    Article  CAS  Google Scholar 

  72. Karrer, P.: The chemistry of vitamin A and C. Chem. Rev. 14, 17–30 (1934)

    Article  CAS  Google Scholar 

  73. Karrer, P.: Vitamines, leurs actions spécifiques et non spécifiques. Bull. Soc. Chim. France 2, 917–937 (1935)

    CAS  Google Scholar 

  74. Karrer, P.: Recent progress in the study of vitamins. Tech. Moderne 28, 54–55 (1936)

    CAS  Google Scholar 

  75. Karrer, P., Fritzsche, H., Ringier, B.H., Salomon, H.: α-Tocopherol. Helv. Chim. Acta 21, 520–525 (1938)

    Article  CAS  Google Scholar 

  76. Karrer, P.: Ueber die Chemie der Flavine. Ergebn. Vitamin Hormonforschung 2, 381–417 (1939)

    CAS  Google Scholar 

  77. Karrer, P.: Recent data on the carotenoid pigments. Bull. Soc. Chim. Biol. 28, 688–699 (1946)

    CAS  Google Scholar 

  78. Karrer, P., Jucker, E.M.: Carotinoide. Birkäuser Publishing Inc., Basel (1948)

    Book  Google Scholar 

  79. Karrer, P.: Lehrbuch der organischen Chemie. Verlag G. Thieme, Leipzig (1927)

    Google Scholar 

  80. Shampo, M.A., Kyle, R.A.: Paul Karrer - Research on vitamins. Mayo Clin. Proc. 75, 328 (2000)

    Article  CAS  PubMed  Google Scholar 

  81. Pringsheim, H., Langhans, A.: Uber Krystallisierte Polysaccharides aus Stärke. Ber. Dtsch. Chem. Ges. 45, 2533–2546 (1912)

    Article  Google Scholar 

  82. Pringsheim, H., Eissler, F.: Über Schardingers Krystallisierte Dextrin (Beiträge zur chemie der stärke, II.). Ber. Dtsch. Chem. Ges. 46, 2959–2974 (1913)

    Article  Google Scholar 

  83. Pringsheim, H., Eissler, F.: Über Schardingers Krystallisierte Dextrin (Beiträge zur chemie der stärke, III.). Ber. Dtsch. Chem. Ges. 47, 2565–2572 (1914)

    Article  CAS  Google Scholar 

  84. Pringsheim, H.: Neue ergebnisse der Stärkechemie. Naturwissenschaften 3, 95–99 (1915)

    Article  CAS  Google Scholar 

  85. Pringsheim, H., Lichtenstein, S.: On crystallized polysaccharides from glycogen. Ber. Dtsch. Chem. Ges. 49, 364–369 (1916)

    Article  CAS  Google Scholar 

  86. Pringsheim, H., Persch, W.: Über die Methylierung der Poly-Amylosen (Beiträge zur Chemie der Stärke, IV). Ber. Dtsch. Chem. Ges. 54, 3162–3168 (1957)

    Article  Google Scholar 

  87. Pringsheim, H.: Problematisches aus der Polysaccharidechemie. Angew. Chemie 35, 345–349 (1922)

    CAS  Google Scholar 

  88. Pictet, A., Jahn, R.: Sur un nouveau produit de dépolymérisation de l’amidon. Helv. Chim. Acta 5, 640–644 (1922)

    Article  CAS  Google Scholar 

  89. Freudenberg, K., Jacobi, R.: Über Schardinger dextrin aus stärke. Justus Liebigs Ann. Chem. 518, 102–108 (1935)

    Article  CAS  Google Scholar 

  90. Freudenberg, K., Rapp, W.: Zur Kenntnis der Stärke und der Schardinger-dextrine. Ber. Dtsch. Chem. Ges. 69, 2041–2045 (1936)

    Article  Google Scholar 

  91. Freudenberg, K., Meyer-Delius, M.: Über die Schardinger-Dextrine aus Stärke. Ber. Dtsch. Chem. Ges. 71, 1596–1600 (1938)

    Article  Google Scholar 

  92. Freudenberg, K.: Polysaccharides and lignin. Annu. Rev. Biochem. 8, 81–112 (1939)

    Article  CAS  Google Scholar 

  93. Freudenberg, K., Schaaf, E., Dumpert, G., Ploetz, T.: Neue Ansichten über die Stärke. Naturwissenschaften 27, 850–853 (1939)

    Article  CAS  Google Scholar 

  94. Freudenberg, K.: Beiträge zur Chemie der Kohlenhydrate. Ber. Dtsch. Chem. Ges. 76, A71–A96 (1943)

    Article  Google Scholar 

  95. French, D., Rundle, R.E.: The molecular weights of the Schardinger alpha and beta dextrins. J. Am. Chem. Soc. 64, 1651–1653 (1942)

    Article  CAS  Google Scholar 

  96. Cramer, F.: Die Cyclodextrine aus Stärke, Dissertation, Heidelberg (1949)

  97. Miekeley, A.: Über die fragliche Existenz der sog. α-Diamylose. Ber. Dtsch. Chem. Ges. 63, 1957–1930 (1930)

    Article  Google Scholar 

  98. Pringsheim, H.: A comprehensive survey of starch chemistry, Chemical Catalog Co. Inc., New York. Walton RP (ed) (1928)

  99. Pringsheim, H.: The dextrins: characteristics, sources, and properties. In: The chemistry of the monosaccharides and of the polysaccharides. New York: McGraw-Hill Book Company, Inc., Cornell University, volume 6, chapter XV, pp. 271–295 (1932)

  100. Crini, G.: Twenty years of dextrin research: a tribute to Professor Hans Pringsheim (1876–1940). Environ. Chem. Lett. 98, 11–27 (2020)

    CAS  Google Scholar 

  101. Hess, K., Trogus, M., Ulmann, M.: Zur Kenntnis der Modifikationen des α-dextrins von F. Schardinger. Z. Phys. Chem. Abt. B 21, 1–6 (1933)

    Google Scholar 

  102. Ulmann, M., Trogus, M., Hess, K.: Zur Kenntnis des α-Dextrins von F. Schardinger. Ber. Dtsch. Chem. Ges. 65, 682–686 (1932)

    Article  Google Scholar 

  103. Crini, G., Fourmentin, S., Lichtfouse, E.: The history of cyclodextrins. Springer Nature, (2020)

  104. Crini, G., French, A.D., Kainuma, K., Jane, J.L., Szente, L.: Contributions of Dexter French (1918–1981) to cycloamylose/cyclodextrin and starch science. Carbohydr. Polym. 257, 117620 (2021)

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This article is dedicated to my mentor and friend Professor Michel Morcellet (University of Lille, France) on the occasion of his 73th birthday. I would like to thank Benito Casu (1927-2016) (Istituto di Chimica e Biochimica G. Ronzoni, Milan, Italy) and Nadia Morin-Crini (Université Bourgogne Franche-Comté, Besançon, France) for our many exchanges regarding this manuscript, and the reviewers for their valuable comments.

Author information

Authors and Affiliations

  1. Laboratoire Chrono-Environnement, Université Bourgogne Franche-Comté, UFR Sciences et Techniques, UMR 6249, 16 Route de Gray, 25000, Besançon, France

    Grégorio Crini

Authors
  1. Grégorio Crini
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Grégorio Crini.

Ethics declarations

Conflict of interest

The author declares no competing financial interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Crini, G. The contribution of professor Paul Karrer (1889–1971) to dextrins. J Incl Phenom Macrocycl Chem 99, 155–167 (2021). https://doi.org/10.1007/s10847-021-01049-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-021-01049-7

Keywords

Search

Navigation