MIN Yuhang, LIU Siqi, YU Xiaoqin, et al. Simultaneous Determination of 24 Acid Industrial Dyes in Food by Solid Phase Extraction-Ultrahigh Performance Liquid Chromatography-Tandem Mass Spectrometry[J]. Science and Technology of Food Industry, 2024, 45(1): 284−294. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023030164.
Citation: MIN Yuhang, LIU Siqi, YU Xiaoqin, et al. Simultaneous Determination of 24 Acid Industrial Dyes in Food by Solid Phase Extraction-Ultrahigh Performance Liquid Chromatography-Tandem Mass Spectrometry[J]. Science and Technology of Food Industry, 2024, 45(1): 284−294. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2023030164.

Simultaneous Determination of 24 Acid Industrial Dyes in Food by Solid Phase Extraction-Ultrahigh Performance Liquid Chromatography-Tandem Mass Spectrometry

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  • Received Date: March 15, 2023
  • Available Online: November 02, 2023
  • A method based on solid phase extraction (SPE) combined with ultra-high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was established for the determination of 24 acid industrial dyes in food. The sample was extracted with ammonia-ethanol solution (ammonia: absolute ethyl alcohol:water=2:7:1, v/v), the extracting solution was condensed to 1 mL under a stream of nitrogen, then dissolved by 10 mL 5% methanol-water solution. The solution was purified by Agela Cleanert PWAX SPE column. The eluant was dried with nitrogen and dissolved by ammonium acetate acetonitrile solution (10 mmol/L ammonium acetate water:acetonitrile =1:1, v/v), the analytes were separated by the Agilent ZORBAX Eclipse RRHD C18 (3.0 mm×150 mm, 1.8 μm) column using mobile phase gradient with acetonitrile and 10 mmol/L ammonium acetate. The analytes were ionized with negative electrospray ionization (ESI) and analyzed by multiple reaction monitoring (MRM) mode, then quantified by external standard method. The linearity of 24 acid industrial dyes displayed good linearities in the range from 20~300 ng/mL, the correlation coefficients higher than 0.999. The limits of detection (LOD) and quantification (LOQ) were 10 μg/kg and 25 μg/kg. The recoveries at three level spiked levels (25、100、250 μg/kg) were 91.0%~112.7% with the relative standard deviations (n=6) between 0.42% and 4.39%. The method was applied to determine 40 batches of bean products, condiments, aquatic products and meat products each, the acid orange Ⅱ was detected in 2 batches of braised meat samples, the content was 138±2.8 μg/kg and 179±3.7 μg/kg, the red 2G was detected in 2 batches of sausage samples, the content was 320±8.6 μg/kg and 230±6.2 μg/kg. The method is rapid, sensitive and reliable, it can be applied to determine 24 acid industrial dyes in food.
  • [1]
    钟金汤. 偶氮染料及其代谢产物的化学结构与毒性关系的回顾与前瞻[J]. 环境与职业医学,2004,21(1):58−62. [CHUNG Kingthom. Review of the mutagenicity, carcinogenicity and autoimmunity of azo dyes and their metabolites from the perspective of their structure-activity relationships[J]. Journal of Environmental and Occupational Medicine,2004,21(1):58−62.] doi: 10.3969/j.issn.1006-3617.2004.01.017

    CHUNG Kingthom. Review of the mutagenicity, carcinogenicity and autoimmunity of azo dyes and their metabolites from the perspective of their structure-activity relationships[J]. Journal of Environmental and Occupational Medicine, 2004, 21(1): 58−62. doi: 10.3969/j.issn.1006-3617.2004.01.017
    [2]
    MOHAMMED A , SHERIF M , HASAN A I, et al. Toxic effects of chronic exposure to dyes among workers of synthetic textile industries[J]. The Egyptian Journal of Hospital Medicine,2019,74(4):744−751. doi: 10.21608/ejhm.2019.24084
    [3]
    JIANG Lingling LI Kang, YAN Donglin, et al. Toxicity assessment of 4 azo dyes in zebrafish embryos[J]. International Journal of Toxicology,2020,39(2):115−123. doi: 10.1177/1091581819898396
    [4]
    杨涛, 刘俊, 刘卫国, 等. 超高效液相色谱法定量检测干果中20种酸性染料[J]. 食品与发酵工业,2023,49(4):245−249. [YANG Tao, LIU Jun, LIU Weiguo, et al. Simultaneous determination of 20 acid dyes by ultra-high performance liquid chromatography in dried fruits[J]. Food and Fermentation Industries,2023,49(4):245−249.] doi: 10.13995/j.cnki.11-1802/ts.031327

    YANG Tao, LIU Jun, LIU Weiguo, et al. Simultaneous determination of 20 acid dyes by ultra-high performance liquid chromatography in dried fruits[J]. Food and Fermentation Industries, 2023, 49(4): 245−249. doi: 10.13995/j.cnki.11-1802/ts.031327
    [5]
    李静娜, 贺栋梁, 吴晓旻, 等. 武汉市市售灌肠类肉制品中红色2G色素非法使用现状及分析[J]. 中国食品卫生杂志,2013,25(4):348−350. [LI Jingna, HE Dongliang, WU Xiaomin, et al. Investigation and analysis on red 2G in sausage product in Wuhan city[J]. Chinese Journal of Food Hygine,2013,25(4):348−350.] doi: 10.13590/j.cjfh.2013.04.024

    LI Jingna, HE Dongliang, WU Xiaomin, et al. Investigation and analysis on red 2G in sausage product in Wuhan city[J]. Chinese Journal of Food Hygine, 2013, 25(4): 348−350. doi: 10.13590/j.cjfh.2013.04.024
    [6]
    李道霞, 黄丽娟, 唐昌云, 等. 阴离子固相萃取-HPLC法测定肉制品中13种合成色素[J]. 食品研究与开发,2021,42(17):157−164. [LI Daoxia, HUANG Lijuan, TANG Changyun, et al. Determination of 13 synthetic colorants in meat products based on anionic solid phase extraction high performance liquid chromatography[J]. Food Research and Development,2021,42(17):157−164.] doi: 10.12161/j.issn.1005-6521.2021.17.025

    LI Daoxia, HUANG Lijuan, TANG Changyun, et al. Determination of 13 synthetic colorants in meat products based on anionic solid phase extraction high performance liquid chromatography[J]. Food Research and Development, 2021, 42(17): 157−164. doi: 10.12161/j.issn.1005-6521.2021.17.025
    [7]
    浙江检察网. 不法商贩在黄三鱼中添加黄栀 被判销售价款十倍赔偿[EB/OL]. (2020-11-27) [2023-03-08]. http://www.zjjcy.gov.cn/art/2020/11/27/art_31_185345.html. [Zhejiang Procuratorial Network. Illegal traders in yellow three fish to add yellow zhi was sentenced to ten times the sale price compensation[EB/OL]. (2020-11-27) [2023-03-08]. http://www.zjjcy.gov.cn/art/2020/11/27/art_31_185345.html.]

    Zhejiang Procuratorial Network. Illegal traders in yellow three fish to add yellow zhi was sentenced to ten times the sale price compensation[EB/OL]. (2020-11-27) [2023-03-08]. http://www.zjjcy.gov.cn/art/2020/11/27/art_31_185345.html.
    [8]
    南方都市报. 深圳发现毒豆腐 含有工业染料酸性金黄G[EB/OL]. (2008-03-11) [2023-03-08]. http://www.315online.com/baoguang/food/12901.html. [Southern Metropolis Daily. Shenzhen found toxic tofu containing industrial dye acid golden G[EB/OL]. (2008-03-11) [2023-03-08]. http://www.315online.com/baoguang/food/12901.html.]

    Southern Metropolis Daily. Shenzhen found toxic tofu containing industrial dye acid golden G[EB/OL]. (2008-03-11) [2023-03-08]. http://www.315online.com/baoguang/food/12901.html.
    [9]
    夏立娅, 韩媛媛, 匡林鹤, 等. 薄层色谱扫描法同时检测豆制品中碱性橙、皂黄、柠檬黄和日落黄以及辣椒粉中酸性橙Ⅱ、丽春红2R和罗丹明B[J]. 分析实验室,2010,29(6):15−18. [XIA Liya, HAN Yuanyuan, KUANG Linhe, et al. Simultaneous determination of basic orange2, metanil yellow, tartrazine, sunset yellow in bean - product and acid orange Ⅱ, ponceau 2R, rhodanmine B in chili powder by thin-layer chromatographic scanning[J]. Chinese Journal of Analysis Laboratory,2010,29(6):15−18.]

    XIA Liya, HAN Yuanyuan, KUANG Linhe, et al. Simultaneous determination of basic orange2, metanil yellow, tartrazine, sunset yellow in bean - product and acid orange Ⅱ, ponceau 2R, rhodanmine B in chili powder by thin-layer chromatographic scanning[J]. Chinese Journal of Analysis Laboratory, 2010, 29(6): 15−18.
    [10]
    范艳, 孟玮, 朱立鑫, 等. 化学发光酶联免疫法检测苏丹红Ⅰ[J]. 食品科学, 2015, 36(12):209−212. [FAN Yan, MENG Wei, ZHU Lixin, et al. Determination of Sudan Ⅰ by chemiluminescent enzyme immunoassay [J]. Food Science, 2015, 36(12):209−212.]

    FAN Yan, MENG Wei, ZHU Lixin, et al. Determination of Sudan Ⅰ by chemiluminescent enzyme immunoassay [J]. Food Science, 2015, 36(12): 209−212.
    [11]
    SALEEM M N, SHAH A, ULLAH N, et al. Detection and degradation studies of nile blue sulphate using electrochemical and UV-Vis spectroscopic techniques[J]. Catalysts,2023,13(1):141−141. doi: 10.3390/catal13010141
    [12]
    YE Xiwen, HE Jing, LI Ying, et al. Determination of trace azo dyes in textile wastewater by liquid-liquid extraction and dispersive liquid-liquid microextraction coupled with gas chromatography-mass spectrometry[J]. Chinese Journal of Chromatography,2020,38(2):255−263.
    [13]
    DOTSE S C, BUSE T Z, ESRA M, et al. Simultaneous determination of harmful aromatic amine products of azo dyes by gas chromatography-mass spectrometry[J]. Journal of Analytical Chemistry,2020,75(10):1330−1334. doi: 10.1134/S1061934820100044
    [14]
    ZUO X, DI Z, DU Y, et al. Determination of 40 dyes in oxidative hair dye products by high performance liquid chromatography[J]. Chinese Journal of Chromatography,2021,39(11):1222−1229. doi: 10.3724/SP.J.1123.2020.11020
    [15]
    LUANA F, LUCILA C, RIBEIRO, et al. Determination of six synthetic dyes in sports drinks by dispersive solid-phase extraction and HPLC-UV-Vis[J]. Journal of the Brazilian Chemical Society,2017,29(3):602−608.
    [16]
    CHEN S B, LI S, FANG K Y, et al. Rapid determination of 93 banned industrial dyes in beverage, fish, cookie using solid-supported liquid-liquid extraction and ultrahigh-performance liquid chromatography quadrupole orbitrap high-resolution mass spectrometry[J]. Food Chemistry,2022(Sep.15):388.
    [17]
    QI P, ZHOU Q Q, LIN Z H, et al. Qualitative screening and quantitative determination of multiclass water-soluble synthetic dyes in foodstuffs by liquid chromatography coupled to quadrupole Orbitrap mass spectrometry[J]. Food Chemistry,2021(Oct.30):360.
    [18]
    SABREUB H, MOHAMED, ALYAA I S, et al. Evaluation of different Sudan dyes in egyptian food samples utilizing liquid chromatography/tandem mass spectrometry[J]. Food Analytical Methods,2021,14(10):1−13.
    [19]
    闵宇航, 黄璐瑶, 余晓琴, 等. 超高效液相色谱-串联质谱法测定酱卤肉制品中1-甲基咪唑、2-甲基咪唑及4-甲基咪唑[J]. 食品工业科技,2021,42(10):261−266. [MIN Yuhang, HUANG Luyao, YU Xiaoqin, et al. Simultaneous determination of 1-methylimidazole, 2-methylimidazole and 4-methylimidazole in sauced meat products by ultra high performance liquid chromatography-tandem mass spectrometry[J]. Science and Technology of Food Industry,2021,42(10):261−266.] doi: 10.13386/j.issn1002-0306.2020080139

    MIN Yuhang, HUANG Luyao, YU Xiaoqin, et al. Simultaneous determination of 1-methylimidazole, 2-methylimidazole and 4-methylimidazole in sauced meat products by ultra high performance liquid chromatography-tandem mass spectrometry[J]. Science and Technology of Food Industry, 2021, 42(10): 261−266. doi: 10.13386/j.issn1002-0306.2020080139
    [20]
    周剑, 王敏, 杨梦瑞. 液相色谱质谱分析中的基质效应研究[J]. 农产品质量与安全,2018(1):67−70. [ZHOU Jian, WANG Min, YANG Mengrui. Matrix effect in liquid chromatography-mass spectrometry analysis[J]. Quality and Safety of Agro-products,2018(1):67−70.] doi: 10.3969/j.issn.1674-8255.2018.01.013

    ZHOU Jian, WANG Min, YANG Mengrui. Matrix effect in liquid chromatography-mass spectrometry analysis[J]. Quality and Safety of Agro-products, 2018(1): 67−70. doi: 10.3969/j.issn.1674-8255.2018.01.013
    [21]
    刘瑜, 张柏瑀, 毕孝瑞, 等. 超高效液相色谱-四级杆串联离子阱复合质谱法测定肉制品中非法添加的碱性工业染料[J]. 食品安全质量检测学报,2021,12(16):6343−6348. [LIU Yu, ZHANG Boyu, BI Xiaorui, et al. Determination of illegally added basic industrial dyes in meat products by ultra performance liquid chromatography-quadrupole tandem ion trap combined mass spectrometry[J]. Journal of Food Safety & Quality,2021,12(16):6343−6348.]

    LIU Yu, ZHANG Boyu, BI Xiaorui, et al. Determination of illegally added basic industrial dyes in meat products by ultra performance liquid chromatography-quadrupole tandem ion trap combined mass spectrometry[J]. Journal of Food Safety & Quality, 2021, 12(16): 6343−6348.
    [22]
    周佳, 刘子溱, 王丽君, 等. 低共熔溶剂-超高效液相色谱-串联质谱法快速测定肉制品、水产品中3种非法添加工业染料[J]. 食品安全质量检测学报,2022,13(5):1538−1544. [ZHOU Jia, LIU Zizhen, WANG Lijun, et al. Determination of 3 kinds of illegally added industrial dyes in meat and aquatic products by hydrophobicity deep eutectic solvent-ultra performance liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality,2022,13(5):1538−1544.] doi: 10.3969/j.issn.2095-0381.2022.5.spaqzljcjs202205024

    ZHOU Jia, LIU Zizhen, WANG Lijun, et al. Determination of 3 kinds of illegally added industrial dyes in meat and aquatic products by hydrophobicity deep eutectic solvent-ultra performance liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality, 2022, 13(5): 1538−1544. doi: 10.3969/j.issn.2095-0381.2022.5.spaqzljcjs202205024
    [23]
    周庆琼, 林子豪, 曾羲, 等. QuEChERS-液相色谱-串联质谱法同时测定调味品中49种工业染料[J]. 食品安全质量检测学报,2018,9(13):3385−3395. [ZHOU Qingqing, LIN Zihao, ZENG Xi, et al. Simultaneous determination of 49 kinds of industrial dyes in condiments by high performance liquid chromatography-tandem mass spectrometry based on QuEChERS[J]. Journal of Food Safety & Quality,2018,9(13):3385−3395.] doi: 10.3969/j.issn.2095-0381.2018.13.027

    ZHOU Qingqing, LIN Zihao, ZENG Xi, et al. Simultaneous determination of 49 kinds of industrial dyes in condiments by high performance liquid chromatography-tandem mass spectrometry based on QuEChERS[J]. Journal of Food Safety & Quality, 2018, 9(13): 3385−3395. doi: 10.3969/j.issn.2095-0381.2018.13.027
    [24]
    王萍亚, 周勇, 戴意飞, 等. 超高效液相色谱-四级杆飞行时间质谱法快速筛查水产品中28种酸性合成色素[J]. 色谱,2015,33(8):822−829. [WANG Pingya, ZHOU Yong, DAI Yifei, et al. Rapid screening of 28 acidic artificial dyes in fishery products by ultra performance liquid chromatography coupled with quadrupole-time of flight mass spectrometry[J]. Chinese Journal of Chromatography,2015,33(8):822−829.] doi: 10.3724/SP.J.1123.2015.03022

    WANG Pingya, ZHOU Yong, DAI Yifei, et al. Rapid screening of 28 acidic artificial dyes in fishery products by ultra performance liquid chromatography coupled with quadrupole-time of flight mass spectrometry[J]. Chinese Journal of Chromatography, 2015, 33(8): 822−829. doi: 10.3724/SP.J.1123.2015.03022
    [25]
    孙良娟, 李红权, 蔡润斌, 等. 高效液相色谱-串联质谱法测定水产品中9种禁用染料类药物残留[J]. 分析测试学报,2023,42(1):89−95. [SUN Liangjuan, LI Hongquan, CAI Runbin, et al. Determination of 9 kinds of banned dye drugs in aquatic products by high performance liquid chromatography-tandem mass spectrometry[J]. Journal of Instrumental Analysis,2023,42(1):89−95.] doi: 10.19969/j.fxcsxb.22082401

    SUN Liangjuan, LI Hongquan, CAI Runbin, et al. Determination of 9 kinds of banned dye drugs in aquatic products by high performance liquid chromatography-tandem mass spectrometry[J]. Journal of Instrumental Analysis, 2023, 42(1): 89−95. doi: 10.19969/j.fxcsxb.22082401
    [26]
    李露青, 李双, 王春芳, 等. 92种工业染料在四级杆/静电场轨道阱高分辨质谱中的离子化规律[J]. 理化检验-化学分册,2020,56(3):308−314. [CHEN Shubing, LI Shuang, WANG Chunfang, et al. Regularities of ionization of 92 industrial dyestuffs by Q-Orbitrap-high resolution mass spectrometry[J]. Physical Testing and Chemical Analysis(Part B:Chemical Analysis),2020,56(3):308−314.]

    CHEN Shubing, LI Shuang, WANG Chunfang, et al. Regularities of ionization of 92 industrial dyestuffs by Q-Orbitrap-high resolution mass spectrometry[J]. Physical Testing and Chemical Analysis(Part B:Chemical Analysis), 2020, 56(3): 308−314.
    [27]
    冉丹, 罗苏苏, 张可欣, 等. HPLC法检测蜜饯中20种合成着色剂含量[J]. 食品工业科技,2022,43(16):281−289. [RAN Dan, LUO Susu, ZHANG Kexin, et al. Determination of 20 kinds of synthetic colorants in candied fruit by HPLC[J]. Science and Technology of Food Industry,2022,43(16):281−289.] doi: 10.13386/j.issn1002-0306.2021100307

    RAN Dan, LUO Susu, ZHANG Kexin, et al. Determination of 20 kinds of synthetic colorants in candied fruit by HPLC[J]. Science and Technology of Food Industry, 2022, 43(16): 281−289. doi: 10.13386/j.issn1002-0306.2021100307
    [28]
    成杰, 吴安理, 杨如娥, 等. 液相色谱-串联质谱法检测食品中合成染料的研究进展[J]. 食品安全质量检测学报,2021,12(20):7986−7994. [CHENG Jie, WU Anli, YANG Ru'e, et al. Recent progress on detection of synthetic dyes in food by liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality,2021,12(20):7986−7994.] doi: 10.19812/j.cnki.jfsq11-5956/ts.2021.20.012

    CHENG Jie, WU Anli, YANG Ru'e, et al. Recent progress on detection of synthetic dyes in food by liquid chromatography-tandem mass spectrometry[J]. Journal of Food Safety & Quality, 2021, 12(20): 7986−7994. doi: 10.19812/j.cnki.jfsq11-5956/ts.2021.20.012
    [29]
    钟丽琪, 曹进, 钱和, 等. 高效液相色谱法测定食品中可能掺杂的16种工业染料[J]. 食品科学,2021,42(22):305−310. [ZHONG Liqi, CAO Jin, QIAN He, et al. Determination of 16 illegally added industrial dyes in foods by high performance liquid chromatography[J]. Food Science,2021,42(22):305−310.] doi: 10.7506/spkx1002-6630-20201127-286

    ZHONG Liqi, CAO Jin, QIAN He, et al. Determination of 16 illegally added industrial dyes in foods by high performance liquid chromatography[J]. Food Science, 2021, 42(22): 305−310. doi: 10.7506/spkx1002-6630-20201127-286
    [30]
    路勇, 渠岩, 冯楠, 等. 超高效液相色谱-串联四级杆质谱法快速筛查食品中的45种工业染料[J]. 食品科学,2012,33(6):176−180. [LU Yong, QU Yan, FENG Nan, et al. Rapid screening of 45 industrial dyes in foods by ultra performance liquid chromatography-tandem quadrupole mass spectrometry[J]. Food Science,2012,33(6):176−180.]

    LU Yong, QU Yan, FENG Nan, et al. Rapid screening of 45 industrial dyes in foods by ultra performance liquid chromatography-tandem quadrupole mass spectrometry[J]. Food Science, 2012, 33(6): 176−180.
    [31]
    KITTLAUS S, SCHIMANKE J, KEMPE G, et al. Assessment of sample cleanup and matrix effects in the pesticide residue analysis of foods using postcolumn infusion in liquid chromatography-tandem mass spectrometry[J]. Journal of Chromatography A,2011,1218(46):8399−8410. doi: 10.1016/j.chroma.2011.09.054
    [32]
    刘进玺, 秦珊珊, 冯书惠, 等, 高效液相色谱-串联质谱法测定食用菌中农药多残留的基质效应[J]. 食品科学, 2016, 37(18):171−177. [LIU Jinxi, QIN Shanshan, FENG Shuhui, et al. Matrix effects in the analysis of pesticides residues in edible fungi by HPLC-MS/MS[J]. Food Science, 2016, 37(18):171−177.]

    LIU Jinxi, QIN Shanshan, FENG Shuhui, et al. Matrix effects in the analysis of pesticides residues in edible fungi by HPLC-MS/MS[J]. Food Science, 2016, 37(18): 171−177.
    [33]
    BODNAR-BRONIARCZYK M, PAWIŃSKI T, KUNICKI P K. Isotope-labeled versus analog internal standard in LC-MS/MS method for tacrolimus determination in human whole blood samples A compensation of matrix effects[J]. Journal of Chromatography B,2019,1104:220−227. doi: 10.1016/j.jchromb.2018.11.026
    [34]
    YANG P, CHANG J S, WONG J W, et al. Effect of sample dilution on matrix effects in pesticide analysis of several matrices by liquid chromatography-high-resolution mass spectrometry[J]. Journal of Agricultural and Food Chemistry,2015,63(21):5169−5177. doi: 10.1021/jf505168v
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