Analysis of Azodicarbonamide in Food Products by High Performance Liquid Chromatography
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1 J. Fd Hyg. Safety Vol. 25, No. 2, pp. 100~105 (2010),QWTPCN QH (QQF *[IKGPG CPF 5CHGV[ Available online at HPLCÏ º Ïä ܹ æö ý 1 ÂÞŠ 4  2  5 ÂÙ 2  1 ÂÞ 1 ÂÞ Š 3  ù 1 * 1 t t sƒ ƒ s, 2 t t ƒ», 3 t t, 4 t t t, 5 t t» t» Analysis of Azodicarbonamide in Food Products by High Performance Liquid Chromatography Ho-Soo Lim 1, Kyeong-Nyeo Bahn 4, Jun-Hyun Kim 2, Gui-Hyeon Jang 5, Gui-Im Moon 2, Sung-Kwan Park 1, Hyo-Jin Yang 1, Hae-Kyong Park 3, and So-Hee Kim 1 * 1 Food Additives and Packages Division, National Institute of Food and Drug Safety Evaluation, Seoul , Korea 2 Food Additives Standardization Division, Korea Food and Drug Administration, Seoul , Korea 3 Nutrition Policy Division, Korea Food and Drug Administration, Seoul , Korea 4 Imported Food Analysis Division, Center for Food and Drug Analysis, Gyeongin Regional Korea Food and Drug Administraion 5 Health/Functional Food Standardization Division, Korea Food and Drug Administration, Seoul , Korea (Received September 21, 2009/Revised October 19, 2009/Accepted June 19, 2010) ABSTRACT This study was conducted to establish a method to analyze azodicarbonamide (ADA) in wheat flour. A new method using high performance liquid chromatography (HPLC) was developed for the determination of ADA in wheat flour. The recovery rate was 91.93~97.54%. The limit of detection for ADA was 0.02 mg/kg and the limit of quantification was 0.05 mg/kg. The monitoring results for ADA contents using the established methods showed that it was detected as the low value of 0.95 mg/kg in one of 51 flour samples (detection rate : 2%), but not detected in 59 bakery samples. The detected ADA level was suitable to its usage standard, compared to the standard (45 mg/kg). Although the detection rate was very low, the established analytical method of ADA will contribute to the management of ADA in processed foods such as wheat flour and bakery. Key words : Azodicarbonamide, HPLC, Wheat flour, Monitoring t ƒ t t ù wš, t t w, y š. azodicarbonamide (ADA) ƒ ƒ t ƒ, y ry ADAƒ ƒ ƒ w ƒœ t w ƒ ƒš. ADA x ù sww x š ù, w t ƒ x. ù ADA» ƒ w 1 kg 45 mg (45 ppm) w ³ 1) š, *Correspondence to: So-Hee Kim, Food Additives and Packages Division, National Institute of Food and Drug Safety Evaluation, Seoul , Korea Tel: ~8, Fax: mrsksh@korea.kr š ƒ t ƒ 45 ppm w š 3). ù t ƒ» ³ š w wš, x 607 t ù t, y, 50 t w t t ƒ tœ 2,4)., t y t ƒ w t» y w z. ADA t k ADA w y, w y š. t ƒ œ ADA x e y ùp 1) t w ADA w d w w» ƒ w, yw»» v w. 100
2 Analysis of Azodicarbonamide in Food Products by High Performance Liquid Chromatography 101 ADA biurea, semicarbazide (SEM), ethyl carbamate (EC) w t w 5-11). ADA wet flour w biurea (hydrazodicarbonamide) y. Biurea w SEM 0.1% š š 10), ADA 45 mg/kg ƒw ECƒ s³ 2.4 ug/kg 12). ƒ ADA w hidrazine w z w Ÿ» w j m v w š 13-16,17-23) ü ADA w ADA ƒw ƒ þ p y 24) w ƒ ADA w k., t ADA d w» w ADA ww hidrazine w w š ƒ ƒ w y wš w. w, y w ü m ƒ w w w.. Ì Ý ßá Ý Ì t t ADA (Sigma-Aldrich, USA) w, HPLC methanol (Merck, Whitehouse Station, NJ, USA), dimethylforamamide (Burdick and Jackson, Muskego, MI, USA), acetonitrile (Merck, Whitehouse Station, NJ, USA), acetone (Duksan, Korea) w, Quantum Express (Millipore, Billerica, USA) w w 18 MΩ w. w ƒ p w. ADA Ý 2g 10 ml ƒwš 10 kw w. 5,000 rpm 10 w w z ƒw 20 ml w j m v w» 0.45 µm vl w x w. ADA æö HPLC æö ADA w» w HPLC HPLC-PDA system (Beckmann Coutler, Germany), UV rp d w 8453 /ƒ ŸŸ (Agilent Technologies, Palo Alto, CA, USA) w. ƒ ADA w j m v w HPLC. Column Imtakt Unison US-C 18 ( mm, 5 µm) w, column temperature 40 o C. v injection volume 10 µl. ƒ t w 0.7 ml/min w A w š B acetonitrile»» w.»» 0 Bƒ 100%, 7 Bƒ 50%, 12 50%, %, 17 0% f sx w 17. ADA wš w x z, š j m v Á w t ew vj w t w w, w w. e (mg/kg) = ˆ Ž G O ŽVsP G GŽkO sp TTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTTT GˆnkOŽP ADA t t 50 mg 1000 ml v j w 900 ml ƒw 20 q w z þw w t w (50 ppm). t w 0.05, 0.1, 0.5, 1.0, 5.0, 10.0, 25.0 mg/l w t w. æöá ˆ y w ICH Guide line Q2B w 18) w p (specificity), (linearity), z, w (LOD) w (LOQ) z w. z ƒ ADA 10, 20, 50 mg/lƒ ƒwš mw w z xw. ŠŒ Ý ˆ ADA w Fig. 1. ƒwš ƒ w z w wš ƒw HPLC w., dimethyl formamide, dimethylformamide- yw, m mw, z w. p wš w z, wš w ƒ z x w. æö ˆ ADA w mw HPLC Table 1
3 102 Ho-Soo Lim et al. Fig. 1. Flow diagram of the sample preparation for analysis of ADA.. ADA j ù 18) Osborne š f C 18 f mw,, vj e w ùkü š, Imtakt Unison US-C 18 (5 µm, mm) f w. w, w, w Table 1 w. (RT) x ƒ,», ƒ f w» w m p»» w. Fig. 2. HPLC chromatogram and UV/Vis spectrum of ADA standard. d w RT=5.3 e qp Fig. 2, 245 nm 425 nm ùk ü, 245 nm 425 nm q w, Ÿ ƒ ƒ 245 nm q w w. y HPLC Table 1. æöá ˆ p (specificity) w w š w w w t x ADA RT w, RT 5.4 min y w (Fig. 2,3), ADA t q 245 nm x w RT ƒ ADA PDA (Photo Diode Array) spectrum ew y w (Fig. 2,3). ADA w vjƒ p w w y w. (linearity) y»» d ( ) Table 1. HPLC condition for analysis of ADA in foods Parameters Values Instrument Beckman Coulter - System Gold HPLC Software 32 Karat 8.0 Solvent 0 min B 0%, 7 min B 50%, 12.0 min B 50%, 12.1 min B 0%, 17.0 B 0% A : Distilled water B : Acetonitrile Column Imtakt Unison US-C18, 5 µm, mm Run time 17 min Flow rate 0.7 ml/min Detector PDA 245 nm, (Slit with = 4) Column temp. 40 o C Fig. 3. HPLC chromatogram and spectrum of ADA in spiked sample.
4 Analysis of Azodicarbonamide in Food Products by High Performance Liquid Chromatography 103 Table 2. Reproducibility of retention time and peak area of ADA at 10 mg/l Times Retention time(min.) Peak area Mean SD %RSD Table 3. Recovery rates of ADA by various spike level No. ADA spike level (mg/l) Mean SD Recovery rate(%) d w y w» w ADA t ƒƒ 0.05, 0.1, 0.5, 1, 5, 10, 25 mg/l w 3z d w, y = χ R 2 1 yw. ADA RT 5.4 min 7 t 3z w ƒƒ w ADA mg/l ü ƒ 1.0 yw ùkü. p x d w y ùkü, w. w x d w mg/l w. x y w» w ADA t 10z w vj RT w. 10 mg/l ƒ ADA w w, peak RT t r (%RSD) ƒƒ 1.85%, 0.17% 2% x ƒ û ùkû (Table 2). ADA w y w ƒ w z d w Table 3. ADA xw t ƒ œ» ƒ Fig. 4. HPLC chromatogram of ADA at LOQ (10 ug/l, 245 nm). w ³ ƒ z d w. ƒ ADA t ƒ 10, 20, 50 mg/lƒ ƒw z mw, z 90% yw. j m v w (limit of detection, LOD) base-line l 3 wš, w w» w e mw y w yw w w. y t t S/N (signal to noise ration) 3 w ADA w d w (Table 4) 0.02 mg/l ¾ ADA base-line y w. w, w (limit of quantification, LOQ) d w (Fig. 4) 0.05 mg/l ¾ ƒ w. y t ADA hidrazine ww w z Ÿ» w w w»»,, y, z w. w,» š HPLC w» x w dimethylformamide w š wš, silica gel w. Specificity Sensitivity» š x w š q ƒ ù ADA w q. z HPLC-ECD detector w C18 f w ƒ ADA z 87% Table 4. Limit of detection (LOD) and limit of quantification (LOQ) of standard solution (Unit : mg/kg) Standard Wave (nm) LOD (mg/l) LOQ (mg/l) Azodicarbonamide 245 nm nm
5 104 Ho-Soo Lim et al. Table 5. ADA levels in wheat flour and bakery retailed in market Group Sample Number of sample ADA level Tested Detected Range 1 Flours 1) 51 1 N.D. 2) ~ Bakery 59 0 N.D. 1) Wheat flour, flying flour, and making mix are included. 2) N.D.: not detected means below limits of detection (0.02 mg/kg). š šw 18) Osborne w s³ 7% z. ADA Ç æö y ADA ü m 51 ƒ 59 w ADA w Table 5 ùkü. ƒ ADA w ƒ ƒ ƒ o½ƒ 51 1 ADAƒ ù( : 2%),. xw t ƒ œ» ADA ƒ 1kg 45 mg ƒ w ƒ ADA» ww. ù ADA š w w ADA w q, m biurea wƒ ù. ƒ t ADA w wš. ADAƒ ƒ w» w», ùký. ù ADAƒ ùkü, ADAƒ biurea w» 17). ò 2008 t t ww (08081» 092) w w. ADA ƒ» t ƒ ù y w x y k Á z w ADA ƒ ƒ w y wš w. t ADA w f,,,»» mw HPLC w y w, z, z mw. z 91.93~97.54% y w, w (LOD) 0.02 mg/l š, w (LOQ) 0.05 mg/l. y w ƒ 51, 59 w ADA w w ƒ mg/kg ù ( : 2%),. ADA» ƒ 1kg 45 mg w û ùkü. mw y t ADA ƒ, ƒœ t w ADA z» w. Ù 1. Korea Food and Drug Administration: Food Additives Code. Korean Foods Industry Association, Seoul, Korea, pp (2009). 2. National Institute of Food and Drug Safety Evaluation: Analysis of food additives in foods. (2009). 3. United States Food and Drug Administration: 21CFR Azodicarbonamide( -data.fda.gov/ scripts/cdrh/ cfdocs/cfcfr). 4. Korea Food and Drug Administration: Food Standards Code. Korean Foods Industry Association, Seoul, Korea (2008). 5. Food and Agriculture Organization of United Nations. Combined Compendium of Food Additive Specifications - Azodicarbonamide. 69th meeting. Electronic Publishing Policy and Support Branch Communication Division - FAO Weak E.D., Hoseney R.C., Seib P.A.: Determination of azodicarbonamide in wheat flour. Cereal Chem., 53, (1976). 7. Becalski A., Lau B.P.Y., Lewis D., Seaman S.W.: Semicarbazide formation in azodicarbonamide treated flour - A model study. J. Agric. Food Chem., 52, (2004). 8. Noonan G.O., Warner C.R., Hsu W., Begley T.H., Perfetti G.A., Diachenko G.W.: Ther determination of semicarbazide (N-aminourea) in commercial bread products by liquid chromatography-mass spectrometry. J. Agric. Food Chem., 53, (2005). 9. de la Calle M.B, Anklam E.: Semicarbazide - occurrence in food products and state-of-the-art in analytical methods used for its determination. Anal. Bioanal. Chem., 382, (2005). 10. Mulder P.P.J., Beumer B., Rhijn J.A.V.: The determination of biurea: A novel method to discriminate between nitrofuran and azodicarbonamide use in food products. Analytica Chemica Acta, 586, (2007). 11. Food and Agriculture Organization of United Nations. FAO Nutrition Meetings Report (1966). Series 40, A, B, C. Available from: htm. Accessed Aug. 30, Dennis M.J., Massey R.C., Ginn R., Parker I., Crews C., Zimmerli B., Zoller O., Rhyn P., Osborne B.: The effect of azodicarbonamide concentrations on ethyl carbamate concentrations in bread and toast. Food Addit Contam, 14, (1997).
6 Analysis of Azodicarbonamide in Food Products by High Performance Liquid Chromatography Weak, E.D., Hoseney, R.C., Seib, P.A.: Determination of azodicarbonamide in wheat flour. Cereal Chem., 53, (1976). 14. Becalski, A., Lau, B.P.Y., Lewis, D., Seaman, S.W.: Semicarbazide formation in azodicarbonamide treated flour - A model study. J Agric. Food Chem., 52, (2004). 15. de la Calle, M.B., Anklam, E.: Semicarbazide - occurrence in food products and state-of-the-art in analytical methods used for its determination. Anal. Bioanal Chem., 382, (2005). 16. Mulder, P.P.J., Beumer, B., Rhijn, J.A.V.: The determination of biurea : A novel method to discriminate between nitrofuran and azodicarbonamide use in food products. Analytica Chemica Acta, 586, (2007). 17. Stadler, R.H., Mottier, R., Guy, P., Gremaud, E., Varga, N., Lalljie, S., Kintscher, J., Dudler, V., Read, W.A., Castle, L.: Semicarbazide is a minor thermal decomposition product of azodicarbonamide used in the gaskets of certain food jars. Analyst, 129, (2004). 18. Osborne, B.G.: High performance liquid chromatography of azodicarbonamide. Journal of Chromatography, 368, (1986). 19. de Stefanis, V.A.: Analysis of azodicarbonamide in wheat flour by liquid chromatography. Cereal Chem., 65, (1988). 20. Becalski, A., Lau, B.P.Y., Lewis, D., Seaman, S.: Semicarbazide in Canadian bakery products. Food Additives and Contaminants, 23, (2006). 21. Pereira, A.S., Donato, J.L., De Nucci, G.: Implications of the use of semicarbazide as a metabolic target of nitrofurazone contamination in coated products. Food Additives and Cotaminats, 21, (2004). 22. Conant, J.B., Bartlett, P.D.: A quantitative study of semicarbazone formation. J. Am. Chem. Soc., 54, (1932). 23. Canas, B.J., Diacheoko, G.W., Nyman, P.J.: Ethyl carbamate levels resulting from azodicarbonamide use in bread. Food Additives and Contaminants, 14, (1997). 24. Dennis, M.J., Massey, R.C., Ginn, R., Parker, I., Crews, C., Zimmerli, B., Zoller, O., Rhyn, P., Osborne, B.: The effect of azodicarbonamide concentrations on ethyl carbamate concentrations in bread and toast. Food Additives and Contaminats, 14, (1997). 25. La, I.J., Lee, M.C., Park, H.D., Kim, K.P.: Effects of Azodicarbonamide on the Rheology of Wheat Flour Dough and the Quality Characteristics of Bread. J. Korean Soc. Food Sci. Nutr., 33, (2004). 26. ICHG(International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use): ICH Topic Q2G(R1). Validation of analytical procedures: Text and methodology. European Medicines Agency, CPMP/ ICH/381/ ).
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