Derivatization of carbonyl compounds with 2,4-dinitrophenylhydrazine and their subsequent determination by high-performance liquid chromatography

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 879, Issue 17-18, 2011, Pages 1282-1289

  Uchiyama, Shigehisa ^a   Inaba, Yohei ^a   Kunugita, Naoki ^a  

^a NATIONAL INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

2,4 Dinitrophenylhydrazine; Carbonyl compounds; Carboxylic acids; Derivatization; Isomerization; Ozone; Reductive amination

Indexed keywords

2-PICOLINE; [CARBONYL; AMINATION REACTION; ANALYTICAL ERRORS; ANALYTICAL METHOD; DERIVATIZATIONS; DINITROPHENYLHYDRAZINE; DOUBLE BONDS; NEW APPLICATIONS; REDUCTIVE AMINATION; SIMULTANEOUS MEASUREMENT; SINGLE BOND; UV IRRADIATION;

ALDEHYDES; AMINES; CARBOXYLIC ACIDS; ISOMERIZATION; ISOMERS; LIQUID CHROMATOGRAPHY; LIQUIDS; OZONE; PLANTS (BOTANY); STEREOCHEMISTRY;

CARBONYLATION;

2,4 DINITROPHENYLHYDRAZINE; CARBONYL DERIVATIVE; PHTHALALDEHYDE;

ANALYTICAL ERROR; CHEMICAL BOND; CHEMICAL REACTION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; REVIEW; STEREOISOMERISM; ULTRAVIOLET IRRADIATION;

ALDEHYDES; AMINATION; CARBOXYLIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; OZONE; PHENYLHYDRAZINES;

EID: 79955588746     PISSN: 15700232     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jchromb.2010.09.028     Document Type: Review

References (90)

1. Golden R., Pyatt D., Shields P.G. Crit. Rev. Toxicol. 2006, 36:135.
2. McGwin G., Lienert J., Kennedy J.I. Environ. Health Perspect. 2010, 118:313.
3. National-Toxicology-Program Rep. Carcinog. Backgr. Doc. 2010, i.
4. Salthammer T., Mentese S., Marutzky R. Chem. Rev. 2010, 110:2536.
5. IARC IARC Monogr Eval Carcinog Risks Hum 2006, World Health Organization, Lyon, p. 39.
6. Bachand A.M., Mundt K.A., Mundt D.J., Montgomery R.R. Crit. Rev. Toxicol. 2010, 40:85.
7. Beane Freeman L.E., Blair A., Lubin J.H., Stewart P.A., Hayes R.B., Hoover R.N., Hauptmann M. J. Natl. Cancer Inst. 2009, 101:751.
8. Hauptmann M., Stewart P.A., Lubin J.H., Beane Freeman L.E., Hornung R.W., Herrick R.F., Hoover R.N., Fraumeni J.F., Blair A., Hayes R.B. J. Natl. Cancer Inst. 2009, 101:1696.
9. Schwilk E., Zhang L., Smith M.T., Smith A.H., Steinmaus C. J. Occup. Environ. Med. 2010, 52:878.
10. Zhang L., Steinmaus C., Eastmond D.A., Xin X.K., Smith M.T. Mutat. Res. 2009, 681:150.
11. Takeda M., Saijo Y., Yuasa M., Kanazawa A., Araki A., Kishi R. Int. Arch. Occup. Environ. Health 2009, 82:583.
12. Takigawa T., Wang B.L., Saijo Y., Morimoto K., Nakayama K., Tanaka M., Shibata E., Yoshimura T., Chikara H., Ogino K., Kishi R. Int. Arch. Occup. Environ. Health 2010, 83:225.
13. Tillett T. Environ. Health Perspect. 2010, 118:A 131.
14. Boccia S., Hashibe M., Gallì P., De Feo E., Asakage T., Hashimoto T., Hiraki A., Katoh T., Nomura T., Yokoyama A., van Duijn C.M., Ricciardi G., Boffetta P. Cancer Epidemiol. Biomarkers Prev. 2009, 18:248.
15. Druesne-Pecollo N., Tehard B., Mallet Y., Gerber M., Norat T., Hercberg S., Latino-Martel P. Lancet Oncol. 2009, 10:173.
16. Lewis S.J., Davey Smith G. Cancer Epidemiol. Biomarkers Prev. 2005, 14:1967.
17. Sanches-Silva A., Rodríguez-Bernaldo de Quirós A., López-Hernández J., Paseiro-Losada P. J. Chromatogr. A 2004, 1046:75.
18. Cordis G.A., Das D.K., Riedel W. J. Chromatogr. A 1998, 798:117.
19. Lucas D., Ménez J.F., Berthou F., Pennec Y., Floch H.H. J. Chromatogr. 1986, 382:57.
20. Pilz J., Meineke I., Gleiter C.H. J. Chromatogr. B 2000, 742:315.
21. Deng Y., Boomsma F., Yu P.H. Life Sci. 1998, 63:2049.
22. Deng Y., Yu P.H. J. Chromatogr. Sci. 1999, 37:317.
23. Kim S.S., Gallaher D.D., Csallany A.S. Lipids 1999, 34:489.
24. Cordis G.A., Maulik N., Bagchi D., Engelman R.M., Das D.K. J. Chromatogr. 1993, 632:97.
25. Esterbauer H., Cheeseman K.H., Dianzani M.U., Poli G., Slater T.F. Biochem. J. 1982, 208:129.
26. Cordis G.A., Bagchi D., Maulik N., Das D.K. J. Chromatogr. A 1994, 661:181.
27. Determination of Formaldehyde in Ambient Air Using Adsorbent Cartridge Followed by High Performance Liquid Chromatography (HPLC), Compendium method TO-11A 1999, U.S. Environmental Protection Agency, Research Triangle Park, NC.
28. Determination of Carbonyl Compounds by High Performance Liquid Chromatography (HPLC), USEPA Method 8315A 1996, U.S. Environmental Protection Agency, Cincinnati, OH.
29. Allen C.F.H. J. Am. Chem. Soc. 1930, 52:2955.
30. Brady O.L. J. Chem. Soc. 1931, 756.
31. Bruice P.Y. Organic Chemistry 2003, Prentice Hall, NJ. 4th edition.
32. Grosjean D. Environ. Sci. Technol. 1982, 16:254.
33. Andersson G., Andersson K., Nilsson C.A., Levin J.O. Chemosphere 1979, 8:823.
34. Andersson K., Hallgren C., Levin J.O., Nilsson C.A. Chemosphere 1981, 10:275.
35. Beasley R.K., Hoffmann C.E., Rueppel M.L., Worley J.W. Anal. Chem. 1980, 52:1110.
36. Guenier J.P., Simon P., Delcourt J., Didierjean M.F., Lefevre C., Muller J. Chromatographia 1984, 18:137.
37. Grosjean D., Fung K. Anal. Chem. 1982, 54:1221.
38. Kuwata K., Uebori M., Yamasaki H., Kuge Y., Kiso Y. Anal. Chem. 1983, 55:2013.
39. Lipari F., Swarin S.J. Environ. Sci. Technol. 1985, 19:70.
40. Levin J.O., Andersson K., Lindahl R., Nilsson C.A. Anal. Chem. 1985, 57:1032.
41. Stafiej A., Pyrzynska K., Ranz A., Lankmayr E. J. Biochem. Biophys. Methods 2006, 69:15.
42. Koivusalmi E., Haatainen E., Root A. Anal. Chem. 1998, 71:86.
43. Grosjean D., Williams Ii E.L. Atmos. Environ. 1992, 26:2923.
44. Richardson S.D. J. Environ. Monit. 2002, 4:1.
45. Zwiener C., Frimmel F.H. Anal. Bioanal. Chem. 2004, 378:862.
46. Zwiener C., Glauner T., Frimmel F.H. Anal. Bioanal. Chem. 2002, 372:615.
47. Arnts R.R., Tejada S.B. Environ. Sci. Technol. 1989, 23:1428.
48. Smith D.F., Kleindienst T.E., Hudgens E.E. J. Chromatogr. 1989, 483:431.
49. Rodier D.R., Nondek L., Birks J.W. Environ. Sci. Technol. 1993, 27:2814.
50. Karst U., Binding N., Cammann K., Witting U. Fresenius J. Anal. Chem. 1993, 345:48.
51. Binding N., Müller W., Witting U. Fresenius J. Anal. Chem. 1996, 356:315.
52. Ramirez F., Kirby A.F. J. Am. Chem. Soc. 1954, 76:1037.
53. Uralets V.P., Rijks J.A., Leclercq P.A. J. Chromatogr. 1980, 194:135.
54. Behforouz M., Bolan J.L., Flynt M.S. J. Org. Chem. 1985, 50:1186.
55. Tayyari S.F., Speakman J.L., Arnold M.B., Cai W., Behforouz M. J. Chem. Soc., Perkin Trans. 1998, 2:2195.
56. Uchiyama S., Ando M., Aoyagi S. J. Chromatogr. A 2003, 996:95.
57. Uchiyama S., Matsushima E., Aoyagi S., Ando M. Anal. Chim. Acta 2004, 523:157.
58. Uchiyama S., Kaneko T., Tokunaga H., Ando M., Otsubo Y. Anal. Chim. Acta 2007, 605:198.
59. Borch R.F., Hassid A.I. J. Org. Chem. 1972, 37:1673.
60. Borch R.F., Bernstein M.D., Durst H.D. J. Am. Chem. Soc. 1971, 93:2897.
61. Zhang J., Blazecka P.G., Davidson J.G. Org. Lett. 2003, 5:553.
62. Beshore D.C., Dinsmore C.J. Org. Lett. 2002, 4:1201.
63. Dinsmore C.J., Zartman C.B. Tetrahedron Lett. 2000, 41:6309.
64. Abdel-Magid A.F., Carson K.G., Harris B.D., Maryanoff C.A., Shah R.D. J. Org. Chem. 1996, 61:3849.
65. Abdel-Magid A.F., Maryanoff C.A., Carson K.G. Tetrahedron Lett. 1990, 31:5595.
66. Pelter A., Rosser R.M., Mills S. J. Chem. Soc., Perkin Trans. 1984, 1:717.
67. Bomann M.D., Guch I.C., DiMare M. J. Org. Chem. 1995, 60:5995.
68. Moormann A.E. Synth. Commun. 1993, 23:789.
69. Miriyala B., Bhattacharyya S., Williamson J.S. Tetrahedron 2004, 60:1463.
70. Kumpaty H.J., Williamson J.S., Bhattacharyya S. Synth. Commun. 2003, 33:1411.
71. Neidigh K.A., Avery M.A., Williamson J.S., Sukanta B. J. Chem. Soc., Perkin Trans. 1998, 1:2527.
72. Bhattacharyya S. J. Org. Chem. 1995, 60:4928.
73. Yoon N.M., Kim E.G., Son H.S., Choi J. Synth. Commun. 1993, 23:1595.
74. Ranu B.C., Majee A., Sarkar A. J. Org. Chem. 1998, 63:370.
75. Apodaca R., Xiao W. Org. Lett. 2001, 3:1745.
76. Ryschkewitsch G.E., Birnbaum E.R. Inorg. Chem. 1965, 4:575.
77. Baldwin R., Washburn R. J. Org. Chem. 1961, 26:3549.
78. Brown H.C., Domash L. J. Am. Chem. Soc. 1956, 78:5384.
79. Sato S., Sakamoto T., Miyazawa E., Kikugawa Y. Tetrahedron 2004, 60:7899.
80. Uchiyama S., Inaba Y., Matsumoto M., Suzuki G. Anal. Chem. 2009, 81:485.
81. Rideout K., Teschke K., Dimich-Ward H., Kennedy S.M. J. Hosp. Infect. 2005, 59:4.
82. Kobayashi K., Tanaka M., Kawai S. J. Chromatogr. 1980, 187:413.
83. Tsai S.W., Hee S.S. Appl. Occup. Environ. Hyg. 1999, 14:255.
84. Wellons S.L., Trawick E.G., Stowers M.F., Jordan S.L., Wass T.L. Am. Ind. Hyg. Assoc. J. 1998, 59:96.
85. W. Hendricks, Glutaraldehyde (OSHA Method 64), Salt Lake City, UT, 1987.
86. Glutaraldehyde (NIOSH) Method 2532 1994, 1st ed.
87. Uchiyama S., Matsushima E., Tokunaga H., Otsubo Y., Ando M. J. Chromatogr. A 2006, 1116:165.
88. Uchiyama S., Matsushima E., Aoyagi S., Ando M. Anal. Chem. 2004, 76:5849.
89. Uchiyama S., Otsubo Y. Anal. Chem. 2008, 80:3285.
90. Uchiyama S., Naito S., Matsumoto M., Inaba Y., Kunugita N. Anal. Chem. 2009, 81:6552.