Abstract
3-Bromoacetyl-7-methoxycoumarin (I) was synthesized as a highly reactive fluorescent derivatization reagent for use in high-performance liquid chromatographic analysis. Compound I readily reacted with carboxylic acids in acetone at room temperature for 30 min in the presence of potassium bicarbonate and 18-crown-6 (Method A), or an anion-exchange resin (Method B) as catalysts to give the corresponding fluorescent carboxylic acid coumarinacyl esters (IIa - o). When lauric acid as a test sample was derivatized with I by use of Methods A and B, the detection limits were 0.4 and 0.5 pmol per injection (S/N=3), respectively. These methods were applicable to the measurements of free fatty acids in human plasma (10–100 μl). Method B used a weakly basic anion-exchange resin instead of catalysts so in Method A, so it would be useful for the simplification of derivatization.
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References
S. Lam and E. Glushka, J, Chromatogr., 158, 207 (1978).
R. Farionotti, Ph. Siard, J. Bouson, S. Kirkiacharian, B. Valeur and G. Mahuzier, J. Chromatogr., 269, 81 (1983).
H. Tsuchiya, T. Hayashi, M. Sato, M. Tatsumi and N. Takagi, J. Chromatogr., 309, 43 (1984).
S. A. Baker, J. A. Monti, S. T. Christain, F. Benington and R. D. Morin, Anal. Biochem., 107, 116 (1980).
W. D. Korte, J. Chromatogr., 243, 153 (1982).
N. Nishimura and T. Kinoshita, Anal. Lett., 13(A3), 191 (1980).
W. D. Watkins and M. B. Peterson, Anal. Biochem., 124, 30 (1982).
K. Nakashima, A. Takeya, S. Nakatsuji, J. Tsunetsugu and S. Akiyama, Bunseki Kagaku, 38, 558 (1989).
J. B. F. Lloyd, J. Chromatogr., 189, 359 (1980).
M. Ikeda, K. Shimada, T. Sakaguchi and U. Matsumoto, J. Chromatogr., 305, 261 (1984).
S. Kamada, M. Maeda and A. Tsuji, J. Chromatogr., 272, 29 (1983).
M. Takeda, S. Kamada, M. Maeda, A. Tsuji, J. Goto and T. Nambara, Bunseki Kagaku, 33, E249 (1984).
N. Nimura, T. Kinoshita, T. Yoshida, A. Uetake and C. Nakai, Anal. Chem., 60, 2067 (1988).
H. Asukabe, H, Yoneyama, Y. Mori, K. Harada and M. Suzuki, J. Chromatogr., 396, 261 (1987).
M. Yamaguchi, S. Hara, R. Matsunaga, M. Nakamura and Y. Ohkura, Anal. Sci., 1, 295 (1985).
M. Yamaguchi, S. Hara, R. Matsunaga, M. Nakamura and Y. Ohkura, J. Chromatogr., 346, 227 (1985).
M. Yamaguchi, R. Matsunaga, S. Hara and M. Nakamura, J. Chromatogr., 375, 27 (1986).
M. Yamaguchi, R. Matsunaga, K. Fukuda, M. Nakamura and Y. Ohkura, Anal. Biochem., 155, 256 (1986).
H. Naganuma, A. Nakanishi, J. Kondo, K. Watanabe and Y. Kawahara, Sankyo Kenkyusho Nempo, 40, 51 (1988).
S. Goya, A. Takadate, H. Fujino and M. Irikura, Yakugaku Zasshi, 101, 1064 (1981).
S. Goya, A. Takadate and H. Fujino, Yakugaku Zasshi, 102, 63 (1982).
A. Takedate, T. Tahara, H. Fujino and S. Goya, Chem. Pharm. Bull., 30, 4120 (1982).
Y.-M. Lee, H. Nakamura and T. Nakajima, Anal. Sci., 5, 681 (1989).
A. Takadate, H. Hiraga, H. Fujino and S. Goya, Chem. Pharm. Bull, 33, 5092 (1985).
F. A. L. van der Horst, M. H. Post and J. J. M. Holthuis, J. Chromatogr., 456, 201 (1988).
F. A. L. van der Horst, J. M. Reijin, M. H. Post and A. Bult, J. Chromatogr., 507, 351 (1990).
S. Rangaswami, T. R. Seshadri and V. Venkateswarlu, Proc. Indian Acad. Sci, 13A, 316 (1941).
This compound was synthesized from 7-methoxycouma-rin-3-carbonyl chloride (W. Baker and C. B. Collis, J. Chem. Soc., 1949, S12) in our laboratory.
C. A. Parker and W. T. Rees, Analyst [London], 85, 587 (1960).
S. Kajigaeshi, T. Kakinami, T. Okamoto and S. Fujisaki, Bull. Chem. Soc. Jpn., 60, 1159 (1987).
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Takadate, A., Masuda, T., Tajima, C. et al. 3-Bromoacetyl-7-methoxycoumarin as a New Fluorescent Derivatization Reagent for Carboxylic Acids in High-Performance Liquid Chromatography. ANAL. SCI. 8, 663–668 (1992). https://doi.org/10.2116/analsci.8.663
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DOI: https://doi.org/10.2116/analsci.8.663