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Journal of the American Oil Chemists Society

, Volume 40, Issue 8, pp 319–329 | Cite as

A review on petroselinic acid and its derivatives

  • Lida L. Placek
Technical

Abstract

This publication contains a comprehensive review of literature on petroselinic acid and its derivatives. All known sources of petroselinic acid including its synthetic derivation have been explored and described. The different plant species, whose seeds offer an oil reported to contain petroselinic acid, have been listed and the amounts of oil and their prevalent fatty acid components given. Its method of isolation from the naturally occurring triglycerides and identification have been discussed. The descriptions of characteristics and properties of petroselinic acid and its various derivatives are also included. In many cases they have been compared to oleic acid and other related fatty acids and their derivatives. The various methods of chemical modification of petroselinic acid have been, investigated and the derivatives obtained have been summarized in tabular form. Some potential uses for petroselinic acid and the products obtained from it have also been discussed. This review was designed to show that is known about petroselinic acid to date, and perhaps to create further interest in research on this unique naturally occurring octadecenoic acid.

Keywords

Elaidic Acid Octadecenoic Acid Mixed Fatty Acid Petroselinic Acid Dihydroxystearic Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. 1.
    Ackman, R. G., P. Linstead, B. J. Wakefield, and B. C. L. Weedon, Tetrahedron8, 221–238 (1960).CrossRefGoogle Scholar
  2. 1a.
    Afanasievski, I., J. Russ. Phys. Chem. Soc.47, 2124–2127 (1915).Google Scholar
  3. 2.
    Arbuzov, B. A., and B. P. Lugovkin, Sbornik Statej Obschei Khim. Akad. Nauk, SSSR1, 419–424 (1953). C. A.49, 847.Google Scholar
  4. 3.
    Artom, C., and M. Swanson, J. Biol. Chem.148, 633–639 (1943).Google Scholar
  5. 4.
    Bailey, L. H., The Standard Cyclopedia of Horticulture, 2476–2477, The Macmillan Co., N. Y., 1939.Google Scholar
  6. 5.
    Baker, B. W., R. W. Kierstead, R. P. Linstead, and B. C. L. Weedon, J. Chem. Soc.,1954, 1804–1808.Google Scholar
  7. 6.
    Ballance, P. E., and W. M. Crombie, Biochem. J.69, 632–640 (1958).PubMedGoogle Scholar
  8. 7.
    Begemann, P. H., J. G. Keppler, and H. A. Boekenoogen, Rec. Trav. Chim.69, 439–456 (1950).CrossRefGoogle Scholar
  9. 8.
    Blekkingh, J. J. A., H. J. J. Jansen, and J. G. Keppler,Ibid. 76, 35–48 (1957).CrossRefGoogle Scholar
  10. 9.
    Boelhouwer, C., J. Gerckens, O. T. Lie, and H. I. Waterman, JAOCS30, 59–61 (1953).Google Scholar
  11. 10.
    Borisyuk, Yu. G., and G. V. Makarova, Nekotorye Voprosy Farm., Sbornik Nauk Trudov Vyssh. Farm. Ucheb. Zavedenii Ukr. SSR.,1956, 179–184, C. A.63, 20844.Google Scholar
  12. 11.
    Bose, P. K., and S. N. Dutt, J. Indian Chem. Soc.17, 49 (1940).Google Scholar
  13. 12.
    Bugorkova, A. A., L. N. Petrova, and V. M. Rodionov, J. Gen. Chem. USSR23, 1915–1920 (1953).Google Scholar
  14. 13.
    Cattaneo, P., G. Karman de Sutton, and G. A. Robles, Rev. Brasil Quim (Sao Paulo)32, 387 (1951).Google Scholar
  15. 14.
    Cattaneo, P., G. Karman de Sutton, and G. A. Robles, Anales Asoc. Quim. Argentina39, 145–158 (1951).Google Scholar
  16. 15.
    Chernoyarova, A. A., J. Gen. Chem. USSR9, 149–152 (1939). C. A.33, 6239.Google Scholar
  17. 16.
    Chernoyarova, A. A.,Ibid. 9, 178–181 (1939).Google Scholar
  18. 17.
    Chernoyarova, A. A.,Ibid. 10, 146–149 (1940).Google Scholar
  19. 18.
    Chernoyarova, A. A., Zhur. Obsh. Khim. SSSR16, 199–202 (1946).Google Scholar
  20. 19.
    Christian, B. C., and T. P. Hilditch, Biochem J.23, 327–338 (1929).PubMedGoogle Scholar
  21. 20.
    Clemo, G. R., and R. Stevens, J. Chem. Soc.1952, 4684–4685.Google Scholar
  22. 21.
    Cramp, W. A., F. J. Julietti, J. F. McGhie, B. L. Rao, and W. A. Ross,Ibid. J. Chem. Soc.1960, 4257–4263.Google Scholar
  23. 22.
    Crombie, L.,Ibid. J. Chem. Soc.1955, 3510–3512.Google Scholar
  24. 23.
    Crombie, W. M. L., R. Comber, and S. G. Boatman, Biochem. J.59, 309–316 (1955).PubMedGoogle Scholar
  25. 23a.
    Dranitsyna, Yu.A., Academia Nauk, SSSR, Botanicheskii Instit, im. V. L. Komarova AN, SSSR, Seria V, Rastitelnoe Syre, 35–39 (1961).Google Scholar
  26. 24.
    Dytham, R. A., and B. C. L. Weedon, Tetrahedron8, 246–260 (1960).CrossRefGoogle Scholar
  27. 25.
    Eibner, A., L. Widenmeyer, and E. Schild, Chem. Umsch. Fette, Oele, Wachse Harze34, 312–320 (1927).Google Scholar
  28. 26.
    Farooq, M. O., M. Kiamuddin, and S. M. Osman, Rec. Trav. Chim.72, 135–138 (1953).CrossRefGoogle Scholar
  29. 27.
    Farooq, M. O., and S. M. Osman, Fette, Seifen, Anstrich.61, 636–639 (1959).CrossRefGoogle Scholar
  30. 28.
    Farooq, M. O., and S. M. Osman, Rec. Trav. Chim.78, 864–871 (1959).CrossRefGoogle Scholar
  31. 29.
    Farooq, M. O., S. M. Osman, and M. S. Ahmad, J. Sci. Food Agr.4, 132–134 (1953).CrossRefGoogle Scholar
  32. 30.
    Farooq, M. O., and M. S. Siddiqui, Fette u. Seifen56, 918–920 (1954).CrossRefGoogle Scholar
  33. 31.
    Farooq, M. O., S. M. Osman, and M. S. Siddiqui, Rec. Trav. Chim.80, 415–421 (1961).CrossRefGoogle Scholar
  34. 32.
    Fialkov, Ya. A., and F. E. Kagan, J. Gen. Chem.27, 2865–2868 (1957).Google Scholar
  35. 33.
    Fitelson, J., JAOCS27, 1–8 (1950).Google Scholar
  36. 34.
    Fore, S. P., and W. G. Bickford, J. Org. Chem.26, 2104–2105 (1961).CrossRefGoogle Scholar
  37. 35.
    Fore, S. P., R. L. Holmes, and W. G. Bickford, JAOCS37, 490–491 (1960).Google Scholar
  38. 36.
    Fore, S. P., T. L. Ward, and F. G. Dollear,Ibid. 40, 30–33 (1963).Google Scholar
  39. 37.
    Gengrinovich, A. I., F. E. Kagan, and Ya. A. Fialkov, Trudy Komissii Anal. Khim., Akad. Nauk SSSR, Otdel Khim. Nauk5 (8), 237–261 (1954), C. A.49, 12179.Google Scholar
  40. 38.
    Gold, J., and J. H. Skellon, J. Appl. Chem. (London)9, 389–395 (1959).Google Scholar
  41. 39.
    Griffiths, H. N., and T. P. Hilditch, J. Chem. Soc.1932, 2315–2324.Google Scholar
  42. 40.
    Grimme, C., Pharm. Zentr.52, 661–667 (1911).Google Scholar
  43. 41.
    Grindley, D. N., J. Sci. Food Agr.1, 53–56 (1950).CrossRefGoogle Scholar
  44. 42.
    Hilditch, T. P., and J. J. Jones, J. Soc. Chem. Ind.46, 174–177T (1927).Google Scholar
  45. 43.
    Hilditch, T. P., and J. J. Jones, Biochem. J.22, 326–330 (1928).PubMedGoogle Scholar
  46. 44.
    Holman, R. T., and P. R. Edmondson, Anal. Chem.28, 1533–1538 (1956).CrossRefGoogle Scholar
  47. 45.
    Holman, R. T., and W. T. Williams, J. Am. Chem. Soc.73, 5285–5289 (1951).CrossRefGoogle Scholar
  48. 46.
    Holmes, R. L., J. P. Moreau, and R. T. O'Connor, JAOCS39, 411–414 (1962).Google Scholar
  49. 47.
    Hughes, A. H., J. Chem. Soc.1933, 338—344.Google Scholar
  50. 48.
    Hughes, A. H., and E. K. Rideal, Proc. Roy. Soc. (London)A140, 253–269 (1933).ADSGoogle Scholar
  51. 49.
    Julietti, F. J., J. F. McGhie, B. L. Rao, W. A. Ross, and W. A. Gramp, J. Chem. Soc.1960, 4514–4521.Google Scholar
  52. 50.
    Kashimoto, T., Nippon Kagaku Zasshi79, 403–406 (1958).Google Scholar
  53. 51.
    Kashimoto, T., and K. Noda,Ibid. 79, 873–876 (1958).Google Scholar
  54. 52.
    Kolb, D. K., and J. B. Brown, JAOCS32, 357–361 (1955).Google Scholar
  55. 53.
    Koyama, Yo., T. Hisatsume, S. Ito, and Yo. Toyama, Mem. Fac. Eng. Nagoya Univ.11, 196–203 (1959), C. A.55, 11884.Google Scholar
  56. 54.
    Kurono, G., J. Pharm. Soc. Japan73, 1213–1216 (1953).Google Scholar
  57. 55.
    Kurono, G., and T. Ishida,Ibid. 72, 684–685 (1952).Google Scholar
  58. 56.
    Kurono, G., and T. Ishida,Ibid. 72, 685–686 (1952).Google Scholar
  59. 57.
    Kurono, G., and T. Ishida,Ibid. 72, 1436–1439 (1952).Google Scholar
  60. 58.
    Kurono, G., and T. Ishida,Ibid. 73, 1211–1213 (1953).Google Scholar
  61. 59.
    Kurono, G., and T. Sakai,Ibid. 72, 471–473 (1952).Google Scholar
  62. 60.
    Kurono, G., and T. Sakai,Ibid. 72, 476–478 (1952).Google Scholar
  63. 61.
    Kurono, G., and T. Sakai,Ibid. 73, 608–610 (1953).Google Scholar
  64. 62.
    Kurono, G., and T. Sakai,Ibid. 73, 610–612 (1953).Google Scholar
  65. 63.
    Kurono, G., and T. Sakai,Ibid. 73 612–614 (1953).Google Scholar
  66. 64.
    Kurono, G., and T. Sakai,Ibid. 73, 1207–1209 (1953).Google Scholar
  67. 65.
    Kurono, G., and T. Sakai,Ibid. 73 1209–1211 (1953).Google Scholar
  68. 66.
    Kurono, G., and T. Sakai,Ibid. 75 580–582 (1955).Google Scholar
  69. 67.
    Kurono, G., T. Sakai, and T. Ishida,Ibid. 72, 174–175 (1952).Google Scholar
  70. 68.
    Kurono, G., T. Sakai, and T. Ishida,Ibid. 72, 1434–1436 (1952).Google Scholar
  71. 69.
    Kurono, G., T. Sakai, and T. Ishida,Ibid. 73, 605–608 (1953).Google Scholar
  72. 70.
    Kurono, G., T. Sakai, and I. Seki, Ann. Rept. Fac. Pharm. Kanazawa Univ.4, 1–6 (1954).Google Scholar
  73. 71.
    Kurono, G., T. Sakai, and I. Seki,Ibid. 4, No. 5, 1–4 (1955). C. A.50, 15103.Google Scholar
  74. 72.
    Kurono, G., T. Sakai, K. Tochiori, and K. Fekuda, Kanazawa Daigaku Yakugakubu Kenkyu Nempo7, 1–5 (1957). C. A.52, 4213.Google Scholar
  75. 73.
    Lovern, J. A., D. S. I. R., “Food Investigation Special Report No: 51,” 1942.Google Scholar
  76. 74.
    Lumb, P. B., and J. O. Smith. Chem. & Ind.1952, 358.Google Scholar
  77. 75.
    Lumb, P. B., and J. C. Smith, J. Chem. Soc.1952, 5032–5035.Google Scholar
  78. 76.
    Lutton, E. S., W. F. Huber, A. J. Mabis, and C. B. Stewart, J. Am. Chem. Soc.73, 5206–5210 (1951).CrossRefGoogle Scholar
  79. 77.
    Lutton, E. S., and D. G. Kolp,Ibid. 73, 2733–2735 (1951).CrossRefGoogle Scholar
  80. 78.
    Matuda, S., J. Chem. Soc. Japan61, 201–206 (1940).Google Scholar
  81. 79.
    Menon, K. N., and P. S. Raman, Proc. Indian Acad. Sci.38A, 128–131 (1953).Google Scholar
  82. 80.
    Mikumo, J., J. Soc. Chem. Ind., Japan36, Suppl. Bd., 632–633 (1933). C. A.28, 921.Google Scholar
  83. 80a.
    Mod, R. R., F. C. Magne, and E. L. Skau, Unpublished data.Google Scholar
  84. 81.
    Nanavati, D. D., B. Nath, and J. S. Aggarwal, Chem. & Ind.1956, 82–83.Google Scholar
  85. 82.
    Nguyen, D. N., R. Ryhage, and S. Ställberg-Stenhagen, Arkiv Kemi15, 433–438 (1960).Google Scholar
  86. 83.
    Norkin, G., Masloboino Zhirovoe Delo1929, No: 8, 25–26.Google Scholar
  87. 84.
    Novak, A. F., G. C. Clark, and H. P. Dupuy, AOCS38, 321–324 (1961).Google Scholar
  88. 85.
    Novak, A. F., M. J. Fisher, S. P. Fore, and H. P. Dupuy,Ibid. JAOCS In preparation.Google Scholar
  89. 86.
    Page, I. H., and H. Rudy, Biochem. Z.220, 304–326 (1930).Google Scholar
  90. 87.
    Palazzo, F. C., and A. Tamburello, Atti. Acad. Lincii23, II, 352–356 (1914).Google Scholar
  91. 88.
    Pigulevskii, G. V., and P. A. Artamonov, Zhur. Obsh. Khim. SSSR.12, 510–517 (1942).Google Scholar
  92. 89.
    Pigulevskii, G. V., and P. A. Artamonov, J. Gen. Chem. USSR.22, 1187–1188 (1952).Google Scholar
  93. 90.
    Pigulevskii, G. V., and E. L. Karasik, J. Appl. Chem. USSR9, 284–286 (1936). C. A.30, 6226.Google Scholar
  94. 91.
    Pigulevskii, G. V., I. L. Kuranova, and E. V. Sokolov,Ibid. 32, 957–958 (1959).Google Scholar
  95. 92.
    Pigulevskii, G. V., I. L. Kuranova, and Yu. D. Shenin, J. Gen. Chem. USSR.29, 2413–2415 (1959).Google Scholar
  96. 93.
    Pigulevskii, G. V., and N. Simonova, Zhur. Obsh. Khim. SSSR.9, 1928–1932 (1939).Google Scholar
  97. 94.
    Pigulevskii, G. V., and A. E. Sokolova, J. Gen. Chem. USSR.31, 601–604 (1961).Google Scholar
  98. 95.
    Placek, L. L., and W. G. Bickford, J. Org. Chem.26, 864–866 (1961).CrossRefGoogle Scholar
  99. 96.
    Placek, L. L., and F. G. Dollear, JAOCS39, 347–350 (1962).CrossRefGoogle Scholar
  100. 97.
    Plisov, A. K., and N. P. Bulatskii, J. Gen. Chem. USSR.23, 1845–1847 (1953).Google Scholar
  101. 98.
    Plisov, A. K., and A. I. BykovetzIbid. 23, 637–639 (1953).Google Scholar
  102. 99.
    Plisov, A. K., and A. I. Bykovetz, Trudy Odess. Tekhnol. Inst. Pishchevoi i Kholodil. Prom6, 51–56 (1955). C. A.51, 10370.Google Scholar
  103. 100.
    Plisov, A. K., and N. S. Skornyakova, J. Gen. Chem. USSR.26, 57–60 (1956).Google Scholar
  104. 101.
    Pollock, M. R., G. A. Howard, and B. W. Boughton,Biochem. J. 45, 417–422 (1949).PubMedGoogle Scholar
  105. 102.
    Prakash, O., A. Ram, and J. C. Gupta, J. Proc. Oil Technologists' Assoc., India, Kanpur13, Pt. 1–2, 42–46 (1957).Google Scholar
  106. 103.
    Raman, P. S., Proc. Indian Acad. Sci.44A, 321–330 (1956).Google Scholar
  107. 104.
    Rankov, G., D. Chobanov, and G. Zagorski, Compt. Rend. Acad. Bulgare Sci.10, 185–188 (1957).Google Scholar
  108. 105.
    Rankov, G., A. Iovchev, and L. Davidkova,Ibid. 10, No: 2, 133–136 (1957).Google Scholar
  109. 106.
    Rocket, J., J. Am. Chem. Soc.78, 3190–3193 (1956).CrossRefGoogle Scholar
  110. 107.
    Scherer, Inaugural Dissertation, Strassburg (1909).Google Scholar
  111. 108.
    Schlenk, H., and R. T. Holman, J. Am. Chem. Soc.72, 5001–5004 (1950).CrossRefGoogle Scholar
  112. 109.
    Shenolikar, I. S., and M. R. Subbaram, J. Sci. & Ind. Research, India,18B, 439–441 (1959).Google Scholar
  113. 110.
    Sheth, M. C., and C. M. Desai, Science & Culture, India20, 243–244 (1954).Google Scholar
  114. 111.
    Shreve, O. D., M. R. Heether, H. B. Knight, and D. Swern, Anal. Chem.22, 1261–1264 (1950).CrossRefGoogle Scholar
  115. 112.
    Shreve, O. D., M. R. Heether, H. B. Knight, and D. Swern,Ibid. 22, 1498–1501 (1950).CrossRefGoogle Scholar
  116. 113.
    Singleton, W. S., and T. L. Ward, JAOCS30, 592–594 (1953).Google Scholar
  117. 114.
    Skellon, J. H., and K. E. Andrews, J. Appl. Chem. London5, 245–250 (1955).Google Scholar
  118. 115.
    Skellon, J. H., and J. W. Spence, Chem & Ind., London1952 691.Google Scholar
  119. 116.
    Skellon, J. H., and J. W. Spence, J. Appl. Chem., London3, 10–14 (1953).Google Scholar
  120. 117.
    Skellon, J. H., and J. W. Spence, Chem. & Ind., London1953, 302.Google Scholar
  121. 118.
    Skellon, J. H., and J. W. Spence, Chem. & Ind., London 1954, 75.Google Scholar
  122. 119.
    Small, J., Food18, 268–270 (1949).Google Scholar
  123. 120.
    Steger, A., and J. Van Loon, Rec. Trav. Chim.46, 703–708 (1927).CrossRefGoogle Scholar
  124. 121.
    Steger, A., and J. Van Loon,Ibid. 47, 471–476 (1928).CrossRefGoogle Scholar
  125. 122.
    Steger, A., and J. Van Loon, Z. Untersuch. Lebensm.56, 365–367 (1928).CrossRefGoogle Scholar
  126. 123.
    Steger, A., and J. Van Loon, Rec. Trav. Chim.52, 593–600 (1933).CrossRefGoogle Scholar
  127. 124.
    Stewart, C. B., W. F. Huber, and E. S. Sutton, J. Am. Chem. Soc.73, 5903–5904 (1951).CrossRefGoogle Scholar
  128. 125.
    Susi, H., Anal. Chem.31, 910–913 (1959).CrossRefGoogle Scholar
  129. 126.
    Swern, D., L. P. Witnauer, S. A. Fusari, and J. B. Brown, AOCS32, 539–540 (1955).Google Scholar
  130. 127.
    Tomson, E. G., Trudy Odessk. Tekhnol. Inst. Pishchevoi i Kholodil. Prom.9, No: 2, 101–106 (1959).Google Scholar
  131. 128.
    Tsuijmoto, M., and H. Koyanagi, Bull. Chem. Soc., Japan8, 161–167 (1933).CrossRefGoogle Scholar
  132. 129.
    Twitchell, E. J., Ind. Eng. Chem.13, 806–807 (1921).CrossRefGoogle Scholar
  133. 130.
    Vandenheuvel, F. A., and E. H. Farmer, JAOCS28, 512–513 (1951).Google Scholar
  134. 131.
    Vanin, I. I., and A. A. Chernoyarova, Zhur Obsh. Khim., SSSR.5, 1537–1542 (1935). Also Ber.70B, 624–628 (1937).Google Scholar
  135. 132.
    Van Loon, J., Rec. Trav. Chim.46, 492–500 (1927).CrossRefGoogle Scholar
  136. 133.
    Vil'yams, N. V., and S. V. Vasil'ev, Zhur Obsh Khim., SSSR.18, 77–81 (1948).Google Scholar
  137. 134.
    Vil'yams, N. V., and S. V. Vasil'ev,Ibid. 18, 459–464 (1948).Google Scholar
  138. 135.
    Vioque, E., and R. T. Holman, Anal. Chem.33, 1444 (1961).CrossRefGoogle Scholar
  139. 136.
    Vongerichten, E., and A. Köhler, Ber.42, 1638–1639 (1909).Google Scholar
  140. 137.
    Wachs, W., and J. Wendenburg, Kolloid. Z.156, 35–41 (1909).CrossRefGoogle Scholar
  141. 138.
    Weitkamp, A. W., A. M. Smiljanic, and S. Rothman, J. Am. Chem. Soc.69, 1936–1939 (1947).CrossRefGoogle Scholar
  142. 139.
    The Yearbook of Agriculture. U. S. D. A., Washington, D. C., 544–545 (1961).Google Scholar
  143. 140.
    Zaroiskaya, E. N., and Yu. G. Borisyuk, Sbornik1956, 185–189. Referat. Zhur. Khim.1958, Abstr. No: 2689. C. A.53, 14548.Google Scholar

Copyright information

© The American Oil Chemists' Society 1963

Authors and Affiliations

  • Lida L. Placek
    • 1
  1. 1.Southern Regional Research Laboratory, Southern Utilization Research and Development DivisionU.S.D.A.New Orleans

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