Skip to main content

Abstract

The diverse ways of obtaining 109 hydroxy-ketones and derivatives are described.

Characterization data: Chemical name, Chemical Abstracts Service Registry Number (CAS-RN), molecular formula, molecular weight, spectroscopic data references, physico-chemical properties.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 429.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 549.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 549.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Adam, N. K.: Chem. Zentralbl., 99, 1647 (1928).

    Google Scholar 

  2. Adam, N. K.: Proc. R. Soc. London, Ser. A, 103, 676–687 (1923).

    Article  CAS  Google Scholar 

  3. Adam, N. K.: Proc. R. Soc. London, Ser. A, 119, 628–644 (1928).

    Article  CAS  Google Scholar 

  4. Akhrem, A. A.; Lakhvich, F. A.; Budai, S. I.; Khlebnicova, T. S. and Petrusevich, I. I.: Synthesis, (12), 925–927 (1978).

    Article  Google Scholar 

  5. Armstrong, E. C.; Bent, R. L.; Loria, A.; Thirtle, J. R. and Weissberger, A.: J. Am. Chem. Soc., 82 (8), 1928–1935 (1960).

    Article  CAS  Google Scholar 

  6. Asano, M. and Hase, Z.: J. Pharm. Soc. Jpn., 60 (2), 649–659 (1940).

    Google Scholar 

  7. Asano, M. and Yamaguchi, K.: J. Pharm. Soc. Jpn., 60 (12), 237–242 (1940).

    Google Scholar 

  8. Auwers, K. and Betteridge, F. H.: Z. Phys. Chem., 32, 39–45 (1900).

    CAS  Google Scholar 

  9. Auwers, K. and Wegener, G.: J. Prakt. Chem., 106 (1), 226–252 (1923).

    Article  Google Scholar 

  10. Auwers, K.: Ber. Dtsch. Chem. Ges., 36B (4), 3890–3892 (1903).

    Article  Google Scholar 

  11. Beger, J. and Meerbote, M.: J. Prakt. Chem., 329 (5), 923–926 (1987).

    Article  CAS  Google Scholar 

  12. Bharate, S. B.; Rodge, A.; Joshi, R. K.; Kaur, J.; Srinivasan, S.; Senthil Kumar. S.; Kulkarni-Almeida, A.; Balachandran, S.; Balakrishnan, A. and Vishwakarma, R. A.: Bioorg. Med. Chem. Lett., 18 (24), 6357–6361 (2008).

    Google Scholar 

  13. Bogeski, I.; Mirceski, V. and Hoth, M.: Clinical Chemistry and Laboratory Medicine, 46 (2), 197–203 (2008).

    Article  CAS  Google Scholar 

  14. Braun, J. V.; Anton, E. and Meyer, F.: Ber. Dtsch. Chem. Ges., 74B (11), 1772–1783 (1941).

    Article  Google Scholar 

  15. Büchi, J.; Hirt, R.; Hofmann, T.; Lieberherr, R. and Hurni, H.: Helv. Chim. Acta, 34 (7), 2162–2171 (1951).

    Article  Google Scholar 

  16. Buu-Hoï, N. P. and Séailles, J., Jr.: J. Org. Chem., 20 (5), 606–609 (1955).

    Article  Google Scholar 

  17. Buu-Hoï, N. P.: J. Org. Chem., 18 (12), 1723–1729 (1953).

    Article  Google Scholar 

  18. Buu-Hoï, N. P.: J. Org. Chem., 19 (11), 1770–1773 (1954).

    Article  Google Scholar 

  19. Buu-Hoï, N. P.; Xuong, N. D. and Tien, N. B.: Intern. J. Leprosy, 22, 16 (1954).

    Google Scholar 

  20. Buu-Hoï, N. P.; Xuong, N. D. and Tien, N. B.: J. Org. Chem., 21 (4), 415–418 (1956).

    Article  Google Scholar 

  21. Chiba, K.; Sonoyama, J. and Tada, M.: J. Chem. Soc., Perkin Trans. 1, (12), 1435–1443 (1996).

    Google Scholar 

  22. Cook, A. H.; Heilbron, I. M. and Lewis, F. B.: J. Chem. Soc., 659–661 (1942).

    Google Scholar 

  23. Cooray, N. F.; Jansz, E. R.; Wimalasena, S.; Wijesekara, T. P. and Nair, B. M.: Phytochemistry, 26 (12), 3369–3371 (1987).

    Article  CAS  Google Scholar 

  24. Coowar, D.; Couche, E.; Koncina, E. and Dubois A.: Axoglia Therapeutics, Patent WO 128,038 (2010).

    Google Scholar 

  25. Cravotto, G.; Tagliapietra, S.; Cappello, R.; Palmisano, G.; Curini, M. and Boccalini, M.: Arch. Pharm., 339 (3), 129–132 (2006).

    Article  CAS  Google Scholar 

  26. Credner, H. H.; Kueffner, K.; Laessig, W. and Meier, E. (Agfa-Gevaert A.-G.): Ger. Offen. 2,854,946 (1980); Chem. Abstr., 94, 74660c (1981).

    Google Scholar 

  27. Crevling, T. V.; Haag, D. J. and Abbott, T. I. (to Kodak Ltd.): Brit. 927,895 (1963); Chem. Abstr., 61, 6570g (1964).

    Google Scholar 

  28. Desai, R. D. and Waravdekar, W. S.: Proc. Indian Acad. Sci., 13A, 177–183 (1941).

    CAS  Google Scholar 

  29. Dhanigond, S. M.; Jain, A. K. and Desai, R. M.: Indian J. Technol., 3 (2), 66–68 (1965); Chem. Abstr., 63, 2331c (1965).

    Google Scholar 

  30. Dimmit, J. H.; Soriano, D. S. and Van Der Puy, M. (Allied Corporation): Patent US 4,705,896 (1987).

    Google Scholar 

  31. Dogutan, M.; Filik, H. and Apak, R.: Anal. Chim. Acta, 485 (2), 205–212 (2003).

    Article  CAS  Google Scholar 

  32. Edgerton, W. H. and Burckhalter, J. H.: J. Am. Chem. Soc., 74 (20), 5209–5210 (1952).

    Article  CAS  Google Scholar 

  33. Engelhardt, M.; Fruhstorfer, W.; Hesse, R.; Dennler, B. and Baumer, W. (Merck, E., A.-G.): Ger. Offen. 1,811,322 (1970); Chem. Abstr., 73, 55826m (1970).

    Google Scholar 

  34. Filik, H. and Apak, R.: Sep. Sci. Technol., 29 (15), 2047–2066 (1994); Chem. Abstr., 121, 260260y (1994).

    Google Scholar 

  35. Filik, H. and Apak, R.: Sep. Sci. Technol., 31 (2), 241–258 (1996); Chem. Abstr., 124, 151506z (1996).

    Google Scholar 

  36. Filik, H.: Anal. Lett., 35 (5), 881–894 (2002).

    Article  CAS  Google Scholar 

  37. Filik, H.: Mikrochim. Acta, 140 (3–4), 205–210 (2002).

    Article  CAS  Google Scholar 

  38. Filik, H.; Berker, K. I.; Balkis, N. and Apak, R.: Anal. Chim. Acta, 518 (1–2), 173–179 (2004).

    Article  CAS  Google Scholar 

  39. Frossard, H.; Fatome, M.; Royer, R.; Lechartier, J-P.; Guillaumel, J. and Demerseman, P.: Chim. Ther., 8 (1), 32–35 (1973).

    CAS  Google Scholar 

  40. Fujita, I.; Murata, S.; Kozuki, T.; Irie, K. and Oohashi, N. (Sumitomo Pharma): Jpn. Kokai Tokkyo Koho JP 07 41,459 [95 41,459] (1995); Chem. Abstr., 123, 227818e (1995).

    Google Scholar 

  41. Gerwick, W. and Fenical, W.: Phytochemistry, 21 (3), 633–637 (1982).

    Article  CAS  Google Scholar 

  42. Gevaert Photo-Producten N. V.: Belg. 634,670 (1964); Chem. Abstr., 61, 14830h (1964).

    Google Scholar 

  43. Gilbert, J.; Fuentes, M.; Ojasoo, T.; Dore, J-C. and Pons, M.: J. Med. Chem., 40 (7), 1104–1111 (1997).

    Article  CAS  Google Scholar 

  44. Gurvich, Y. A. and Zimin, Y. B.: Zh. org. Khim., 5 (9), 1609–1610 (1969).

    Google Scholar 

  45. Gurvich, Y. A. and Zimin, Y. B.: Zh. org. Khim., 5 (9), 1658–1660 (1969).

    CAS  Google Scholar 

  46. Gurvich, Y. A.; Zimin, Y. B. and Bel’fer, M. V.: Izobret., Prom. Obraztsy, Tovarnye Znaki, 45 (14), 18–19 (1968); Chem. Abstr., 69, 67109k (1968).

    Google Scholar 

  47. Gurvich, Y. A.; Zimin, Y. B. and Bel’fer, M. V.: U.S.S.R. 215,930 (1968); Chem. Abstr., 69, 67109k (1968).

    Google Scholar 

  48. Hanabusa, K.; Kondo, K. and Takemoto, K.: Makromol. Chem. Phys., 180 (2), 307–314 (1979).

    Article  CAS  Google Scholar 

  49. Hanabusa, K.; Okui, K.; Koyama, T. and Shirai, H. (Shirai, H., TDK K. K.): Jpn. Kokai Tokkyo Koho JP 04,112,863 [92,112,863] (1992); Chem. Abstr., 117, 153382k (1992).

    Google Scholar 

  50. Hanabusa, K.; Oumi, T.; Koyama, T.; Shirai, H.; Hayakawa, T. and Kurose, A.: J. Macromol. Sci., Chem., A26 (10), 1397–1413 (1989).

    Article  CAS  Google Scholar 

  51. Hauptmann, H. and Rotschild, H.: Anais da associacao brasilera de quimica, 10, 254–270 (1951); Chem. Abstr., 48, 3300b (1954) and 49, 2368d (1955).

    Google Scholar 

  52. Haworth, R. D. and Woodcock, D.: J. Chem. Soc., 999–1003 (1946).

    Google Scholar 

  53. Heidemann, E. and Wolframm, C. P.: Rev. Tech. Ind. Cuir, 1973, 65 6–8, 10–14, 16, 18–21; Chem. Abstr., 78, 148992f (1973).

    Google Scholar 

  54. Heinrich, B. and Guillon, D.: Mol. Cryst. Liq. Cryst., 268, 21–43 (1995).

    Article  CAS  Google Scholar 

  55. Hide, K.; Okui, K.; Karaki, K.; Shirai, H. and Iyanagi, K. (Pola Chemical Industries, Inc. Japan): Jpn. Kokai Tokkyo Koho JP 10 245,314 [98 245,314] (1998); Chem. Abstr., 129, 280760e (1998).

    Google Scholar 

  56. Horie, N. and Yamamoto, S. (Otsuka Pharmaceutical Factory, Inc.): Jpn. Kokai Tokkyo Koho JP 03,218,369 [91,218,369] (1991); Chem. Abstr., 116, 41190u (1992).

    Google Scholar 

  57. Horie, T.; Tominaga, H.; Kawamura, Y.; Hada, T.; Ueda, N.; Amano, Y. and Yamamoto, S.: J. Med. Chem., 34 (7), 2169–2176 (1991).

    Article  CAS  Google Scholar 

  58. Hurum, D. C. and Kreilick, R. W.: J. Phys. Chem., 99 (31), 11813–11819 (1995).

    Article  CAS  Google Scholar 

  59. Isaiah, N. H.; Subbarao, R. and Aggarwal, J. S.: J. Chromatogr., 43 (4), 519–522 (1969).

    Article  CAS  Google Scholar 

  60. Johnson, T. B. and Kohmann, E. F.: J. Am. Chem. Soc., 36 (6), 1259–1268 (1914).

    Article  Google Scholar 

  61. Kato, M. J.; Lopes, L. M. X.; Fo, H. F. P.; Yoshida, M. and Gottlieb, O. R.: Phytochemistry, 24 (3), 533–536 (1985).

    Article  CAS  Google Scholar 

  62. Kato, M. J.; Yoshida, M. and Gottlieb, O. R.: Phytochemistry, 29 (6), 1799–1810 (1990).

    Article  CAS  Google Scholar 

  63. Kauffmann, H. and Grombach, A.: Ber. Dtsch. Chem. Ges., 38 (1), 794–801 (1905).

    Article  CAS  Google Scholar 

  64. Kauffmann, H.: Justus Liebigs Ann. Chem., 344 (1–2), 30–77 (1906).

    Article  CAS  Google Scholar 

  65. Konita, T.; Watanabe, H.; Hayashi, T.; Konishi, Y. and Kijima, S. (Eisai Co., Ltd.; Eisai Chemical Co., Ltd.): Jpn. Kokai Tokkyo Koho JP 03,149,287 [91,149,287] (1991); Chem. Abstr., 116, 22156w (1992).

    Google Scholar 

  66. Krafft, F.: Ber. Dtsch. Chem. Ges., 21 (2), 2256–2265 (1888).

    Article  Google Scholar 

  67. Krafft, F.: Ber. Dtsch. Chem. Ges., 21 (2), 2265–2271 (1888).

    Article  Google Scholar 

  68. Krafft, F.: Ber. Dtsch. Chem. Ges., 40 (4), 4779–4784 (1907).

    Article  Google Scholar 

  69. Lacassagne, A.; Duplan, J-F. and Buu-Hoï, N. P.: J. Nat. Cancer Inst., 15 (4), 915–921 (1955).

    CAS  Google Scholar 

  70. Lacassagne, A.; Duplan, J-F. and Buu-Hoï, N. P.: Radiobiology Symposium, Proc., Liège Aug.-Sept., 1954, 64–67 (Pub. 1955); Chem. Abstr., 49, 9820i (1955).

    Google Scholar 

  71. Lakhvich, F. A. and Petrusevich, I. I.: Khim. Prir. Soedin., 4, 580–581 (1989); Chem. Abstr., 112, 157943p (1990).

    Google Scholar 

  72. Lakhvich, F. A.; Petrusevich, I. I.; Sergeeva, A. N.; Buravskaya, T. N.; Polozov, G. I. and Akhrem, A. A.: Dokl. Akad. Nauk SSR, 298, 1395–1397 (1988).

    CAS  Google Scholar 

  73. Lappin, G. R. and Pridgen, H. S. (Eastman Kodak Co.): Patent FR 1,566,404 (1969); Chem. Abstr., 71, 112618e (1969).

    Google Scholar 

  74. Loria, A.; Weissberger, A. and Thirtle, J. R. (Eastman Kodak Co.): Patent US 2,728,659 (1953).

    Google Scholar 

  75. Lubos, B.: Chem. Prumysl., 15 (7), 411–414 (1965); Chem. Abstr., 63, 6807b (1965).

    Google Scholar 

  76. Lunel, M. C.; Favre-Bonvin, J.; Bernillon, J. and Arpin, N.: Tetrahedron, 38 (9), 1235–1239 (1982).

    Article  CAS  Google Scholar 

  77. Majima, R. and Nakamura, I.: Chem. Ber., 46 (3), 4089–4095 (1913).

    Article  Google Scholar 

  78. Majima, R. and Nakamura, I.: Chem. Ber., 48 (2), 1597–1603 (1915).

    Article  CAS  Google Scholar 

  79. Majima, R.; Nagaoka, K. and Yamada, K.: Chem. Ber., 55 (1), 215–217 (1922).

    Article  Google Scholar 

  80. Marei, A.; Kassem, T. M. and Gebril, B. A.: Egypt. J. Chem., 20 (1), 85–100 (1977–1978).

    Google Scholar 

  81. Marei, A.; Kassem, T. M. and Gebril, B. A.: Indian J. Technol., 14 (9), 447–452 (1976).

    CAS  Google Scholar 

  82. Matsuda, S.; Ogawa, M. and Okazaki, T.: Technol. Repts. Osaka Univ., 6, 393–395 (1956); Chem. Abstr., 52, 10930d (1958).

    Google Scholar 

  83. Meshram, H. M.; Reddy, G. S.; Reddy, M. M. and Yadav, J. S.: Synth. Commun., 28 (12), 2203–2206 (1998).

    Article  CAS  Google Scholar 

  84. Mirceski, V.; Gulaboski, R.; Bogeski, I. and Hoth, M.: J. Phys. Chem. C, 111 (16), 6068–6076 (2007).

    Article  CAS  Google Scholar 

  85. Misra, G. C.; Pande, L. M.; Joshi, G. C. and Misra, A. K.: Aust. J. Chem., 25 (7), 1579–1581 (1972).

    Article  CAS  Google Scholar 

  86. Moreau, A.; Rao, P. N. P. and Knaus, E. E.: Bioorg. Med. Chem., 14 (15), 5340–5350 (2006).

    Article  CAS  Google Scholar 

  87. Morimoto, K.; Furuya, K. and Toriuchi, M. (Fuji Photo Film Co., Ltd.): Ger. Offen. DE 3,437,545 (1985); Chem. Abstr., 103, 132286c (1985).

    Google Scholar 

  88. Oki, N. (Fuji Photo Film Co., Ltd.): Jpn. Kokai Tokkyo Koho JP 62,201,436 [87,201,436] (1987); Chem. Abstr., 108, 121985g (1988).

    Google Scholar 

  89. Ozawa, H.; Momose, K.; Machida, M.; Natori, S. and Yoshihira, K.: Chem. Pharm. Bull., 16 (5), 853–862 (1968).

    Article  CAS  Google Scholar 

  90. Paranjpe, K. D.; Phalnikar, N. L. and Nargund, K. S.: J. Univ. Bombay, 11A Pt. 3, 120–123 (1942).

    Google Scholar 

  91. Popov, Y. V.; Korchagina, T. K.; Ushchenko, V. P. and Gross, A. I.: Russ. J. Org. Chem., 40 (6), 912–913 (2004);

    Article  CAS  Google Scholar 

  92. Prasad, A. K.; Pati, H. N.; Azim, A.; Trikha, S. and Poonam: Bioorg. Med. Chem., 7 (9), 1973–1977 (1999).

    CAS  Google Scholar 

  93. Ralston, A. W. and Bauer, S. T.: J. Org. Chem., 5 (2), 165–170 (1940).

    Article  CAS  Google Scholar 

  94. Ralston, A. W.; Ingle, A. and McCorkle, M. R.: J. Org. Chem., 7 (6), 457–461 (1942).

    Article  CAS  Google Scholar 

  95. Ralston, A. W.; McCorkle, M. R. and Bauer, S. T.: J. Org. Chem., 5 (6), 645–659 (1940).

    Article  CAS  Google Scholar 

  96. Ranu, B. C.; Ghosh, K. and Jana, U.: J. Org. Chem., 61 (26), 9546–9547 (1996).

    Article  CAS  Google Scholar 

  97. Rayet, P.; Prost, M. and Urbain, M.: Helv. Chim. Acta, 39 (11), 87–98 (1956).

    Article  CAS  Google Scholar 

  98. Richert-Mellier, M. T.: Oleagineux, 17, 491–494 (1962).

    CAS  Google Scholar 

  99. Royer, R. and Bisagni, E.: Bull. Soc. Chim. Fr., 486–492 (1954).

    Google Scholar 

  100. Runti, C. and Ulian, F.: Farmaco, Ed. Sci., 23 (2), 122–130 (1968).

    CAS  Google Scholar 

  101. Sanko Kaihatsu Kagaku Kenkyusho Kanzaki Paper Mfg. Co. Ltd.: Jpn. Kokai Tokkyo Koho JP 59,175,448 [84,175,448 ] (1984); Chem. Abstr., 102, 113043j (1985).

    Google Scholar 

  102. Shi, J-L.; Chen, X. and Jiang, X-K.: J. Org. Chem., 61 (14), 4698–4702 (1996).

    Article  CAS  Google Scholar 

  103. Strubell, W. and Baumgartel, H.: J. Prakt. Chem., 9 (3–4), 213–216 (1959).

    Article  CAS  Google Scholar 

  104. Suetsugu, M.; Shinojima, S.; Sakamoto, O.; Shibata, Y.; Tanaka, N. and Fujiwara, Y. (Shiseido Co., Ltd., Japan): Jpn. Kokai Tokkyo Koho JP 09,136,814 [97,136,814] (1997); Chem. Abstr., 127, 55661n (1997).

    Google Scholar 

  105. Sugita, S.; Nakagawa, S.; Yoshimoto, S. and Shimada, N. (Konica Co.): Jpn. Kokai Tokkyo Koho JP 63 47,763 [88 47,763] (1988), Chem. Abstr., 109, 160448z (1988).

    Google Scholar 

  106. Thirtle, J. R.; Vittum, P. W. and Weissberger, A. (to Eastman Kodak Co.): Patent US 2,732,300 (1953); Chem. Abstr., 50, 6236d (1956).

    Google Scholar 

  107. Thompson, P. E.; Reinertson, J. W.; Bayles, A.; McCarthy, D. A. and Elslager, E. F.: Am. J. Trop. Med. Hyg., 4 (2), 224–248 (1955); Chem. Abstr., 51, 15005a (1957).

    Google Scholar 

  108. Tripathi, B. N. and Garg, C. L.: Indian J. Chem., 7 (8), 778–779 (1969).

    CAS  Google Scholar 

  109. Tusek, L.: Com. Naz. Energ. Nucl., (Rapp. Tec.) RT-CHI, 74 (5), 17 pp. (1974); Chem. Abstr., 82, 57662q (1975).

    Google Scholar 

  110. Ukita, T.; Nojima, S. and Matsumoto, M.: J. Am. Chem. Soc., 72, (11), 5143–5144 (1950).

    Article  CAS  Google Scholar 

  111. Unger, F.: Liebigs Ann. Chem., 504 (1), 267–286 (1933).

    Article  CAS  Google Scholar 

  112. Van der Puy, M.; Soriano, D. S. and Dimmit, J. H. (Allied Corp.): Eur. Pat. Appl. EP 166,153 (1986); Chem. Abstr., 104, 153209r (1986).

    Google Scholar 

  113. Van Klink, J. W.; Larsen, L.; Perry, N. B.; Weavers, R. T.; Cook, G. M.; Bremer, P. J.; MacKenzie, A. D. and Kirikae, T.: Bioorg. Med. Chem., 13 (24), 6651–6662 (2005).

    Article  Google Scholar 

  114. Watanabe, S.: Kogyo Kagaku Zasshi, 59, 1086–1087 (1956); Chem. Abstr., 52, 10930 (1958).

    Google Scholar 

  115. Yoshihira, K.; Sakaki, S.; Ogawa, H. and Natori, S.: Chem. Pharm. Bull., 16 (12), 2383–2389 (1968).

    Article  CAS  Google Scholar 

  116. Yu, X.; Scheller, D.; Rademacher, O. and Wolff, T.: J. Org. Chem., 68 (19), 7386–7399 (2003).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 2015 Springer International Publishing Switzerland

About this chapter

Cite this chapter

Martin, R., Buisson, JP. (2015). Hexadecanones. In: Aromatic Hydroxyketones: Preparation & Physical Properties. Springer, Cham. https://doi.org/10.1007/978-3-319-14185-5_14

Download citation

Publish with us

Policies and ethics