Improved Method for Determination of Raspberry Ketone in Fragrance Mist by HPLC-Fluorescence Analysis after Pre-Column Derivatization with 4-(N,N-Dimethylaminosulfonyl)-7-(N-chloroformylmethyl-N-methylamino)-2,1,3-benzoxadiazole
Raspberry ketone {RK,
4-(4-hydroxyphenyl)butan-2-one} is structurally resembles
4-(4-hydroxyphenyl)-2-butanol, which causes leukoderma on consumers’ skin.
Therefore, it is important to measure in cosmetics for quality assessment. Very
recently, an HPLC-fluorescence method for determination of RK in a fragrance
mist by pre-column derivatization with 4-hydrazino-7-nitro-2,1,3-benzoxadiazole
hydrazine was established. However, the derivatization conditions (80°C, 20
min) were severe. In this study, an improved pre-column derivatization with 4-(N,N-dimethylaminosulfonyl)-7-(N-chloro-formylmethyl-N-methylamino)-2,1,3-benzoxadiazole
(DBD-COCl) is presented by HPLC-fluorescence method for determination of RK.
The DBD-CO-RK derivative was eluted from a reversed-phase ODS column,
and detected with excitation at 440 nm and emission at 543 nm. Derivatization
was performed at room temperature for 3 min. The retention time of DBD-CO-RK derivative
was 16.8 min. The standard curve was linear in the range of 0.05 to 2.5 μg/mL, with
a correlation coefficient (r2)
value of 0.9988. The lower limit of detection was 0.01 μg/mL (absolute amount of 0.3
pmol). The coefficients of variation were less than 10.0%. The content of RK in
fragrance mist (1.00 mL) was 1.20 ±
0.08 mg (range,
1.10 to 1.31 mg,
References
[1]
Morimoto, C., Satoh, Y, Hara, M., Inoue, S., Tsujita, T. and Okuda, H. (2005) Anti-Obese Action of Raspberry Ketone. Life Sciences, 77, 194-204.
https://doi.org/10.1016/j.lfs.2004.12.029
[2]
Wang, L., Meng, X. and Zhang, F. (2012) Raspberry Ketone Protects Rats Fed High-fat Diets against Nonalcoholic Steatohepatitis. Journal of Medicinal Food, 15, 495-503. https://doi.org/10.1089/jmf.2011.1717
[3]
Park, K.S. (2015) Raspberry Ketone, a Naturally Occurring Phenolic Compound, Inhibits Adipogenic and Lipogenic Gene Expression in 3T3-L1 Adipocytes. Pharmaceutical Biology, 53, 870-875. https://doi.org/10.3109/13880209.2014.946059
[4]
Fukuda, Y., Nagano, M., Arimatsu, Y. and Futatsuka, M. (1998) An Experimental Study on Depigmenting Activity of 4-(p-Hydroxyphenyl)-2-butanone in C57 Black Mice. Journal of Occupational Health, 40, 97-102. https://doi.org/10.1539/joh.40.97
[5]
Victor Lin, C.H., Ding, H.Y., Kuo, S.Y., Chin, L.W., Wu, J.Y. and Chang, T.S. (2011) Evaluation of in Vitro and in Vivo Depigmenting Activity of Raspberry Ketone from Rheum officinale. International Journal of Molecular Sciences, 12, 4819-4835.
https://doi.org/10.3390/ijms12084819
[6]
Kim, M., Baek, H.S., Lee, M., Park, H., Shin, S.S., Choi, D.W. and Lim, K.M. (2016) Rhododenol and Raspberry Ketone Impair the Normal Proliferation of Melanocytes through Reactive Oxygen Species-Dependent Activation of GADD45. Toxicology in Vitro, 32, 339-346. https://doi.org/10.1016/j.tiv.2016.02.003
[7]
Aoyama, Y., Ito, A., Suzuki, K., Suzuki, T., Tanemura, A., Nishigori, C., Ito, M., Katayama, I., Sugiura, S. and Matsunaga, K. (2014) The First Epidemiological Report of Rhododenol-Induced Leukoderma in Japan Based on a Nation-Wide Survey. The Japanese Journal of Dermatology, 124, 2095-2109.
[8]
Fogy, I., Grundmann, H., Schmid, E.R., Huber, J.F.K. and Holzer, H. (1981) High-Pressure Liquid Chromatographic Determination of Raspberry Ketone in Natural and Artificially Aromatized Raspberry Products. Deutsche Lebensmit-tel-Rundschau, 77, 271-275.
[9]
Borejsza-Wysocki, W., Goers, S.K., McArdle, R.N. and Hrazdina, G. (1992) (p-Hydroxyphenyl)butan-2-One Levels in Raspberries Determined by Chromatographic and Organoleptic Methods. Journal of Agricultural and Food Chemistry, 40, 1176-1177. https://doi.org/10.1021/jf00019a018
[10]
Perez, R.L. (1983) Gas Chromatographic Determination of Raspberry Ketone and Malathion in Insect Bait Concentrates. Journal of Chromatography A, 259, 176-180.
https://doi.org/10.1016/S0021-9673(01)87993-0
[11]
Grob, Jr.K. and Stoll, J.M. (1986) Loop-Type Interface for Concurrent Solvent Evaporation in Coupled HPLC-GC. Analysis of Raspberry Ketone in a Raspberry Sauce as an Example. Journal of High Resolution Chromatography, 9, 518-523.
https://doi.org/10.1002/jhrc.1240090906
[12]
Beekwilder, J., van der Meer, I.M., Sibbesen, O., Broekgaarden, M., Qvist, I., Joern D. Mikkelsen, J.D. and Hall, R.D. (2007) Microbial Production of Natural Raspberry Ketone. Biotechnology Journal, 2, 1270-1279.
https://doi.org/10.1002/biot.200700076
[13]
Lili, W., Yansong, W., Yan, Z., Xianjun, M., Lei, Y. and Fengqing, Z. (2011) Deter-mination of Raspberry Ketone in Raspberry by High-Performance Liquid Chromatography Tandem Mass Spectrometry. 2011 International Conference on Human Health and Biomedical Engineering (HHBE), Jilin, 19-22 August 2011, 62-65. https://doi.org/10.1109/HHBE.2011.6027897
[14]
Higashi, Y. (2016) Simple HPLC-fluorescence Determination of Raspberry Ketone in Fragrance Mist after Pre-Column Derivatization with 4-Hydrazino-7-nitro-2,1,3-benzoxadiazole. Journal of Analytical Sciences, Methods and Instrumentation, 6, 44-49. https://doi.org/10.4236/jasmi.2016.62006
[15]
Higashi, Y. (2015) Simple Determination of 17α-Ethynylestradiol in Hair Restorer by High-Performance Liquid Chromatography Coupled with Fluorescence Detection after Pre-Column Derivatization 4-(N-Chloroformylmethyl-N-methylamino) -7-nitro-2,1,3-benzoxadiazole. Austin Chromatography, 2, 1-4.
[16]
Higashi, Y. (2015) Simple HPLC-Fluorescence Determination of Eugenol in Clove Oil after Pre-Column Derivatization with 4-(N-chloroformylmethyl-N-methylamino)-7-nitro-2,1,3-benzoxadiazole. Journal of Analytical Chemistry, 70, 1401-1405.
https://doi.org/10.1134/S1061934815110179
[17]
Higashi, Y. (2015) Development of Simultaneous HPLC-Fluorescence Assay of Phenol and Chlorophenols in Tap Water after Pre-Column Derivatization with 3-Chlorocarbonyl-6,7-dimethoxy-1-methyl-2(1H)-quinoxalinone. Detection, 4, 16-24. https://doi.org/10.4236/detection.2016.41003