Citation: HAN Lin-Xue, QIU Tian, LIN Xiao, LIU Jia-Rong, HU Xiao-Jian, ZHANG Xu. Determination of Four Metabolites of Di(isononyl) Cyclohexane-1,2-dicarboxylate in Urine via Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(2): 229-238. doi: 10.19756/j.issn.0253-3820.221183 shu

Determination of Four Metabolites of Di(isononyl) Cyclohexane-1,2-dicarboxylate in Urine via Ultra High Performance Liquid Chromatography-Tandem Mass Spectrometry

HAN Lin-Xue ¹ ,
QIU Tian ¹ ,
LIN Xiao ¹ ,
LIU Jia-Rong ² ,
HU Xiao-Jian ¹ ,
ZHANG Xu ^1,,

1.
China CDC Key Laboratory of Environment and Population Health, National Institute of Environmental Health, Chinese Center for Disease Control and Prevention, Beijing 100021, China;
2.
Yanjing Medical College, Capital Medical University, Beijing 101300, China

Corresponding author: ZHANG Xu, zhangxu@nieh.chinacdc.cn
Received Date: 15 April 2022
Revised Date: 19 October 2022

Fund Project: Supported by the National Natural Science Foundation of China (No. 22106154), the State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences (No. KF2020-17) and the Project of Hubei Key Laboratory of Environmental and Health Effects of Persistent Toxic Substances (No. PTS2019-08).

A method for quantification of four kinds of metabolites of di(isononyl) cyclohexane-1,2-dicarboxylate (DINCH) in urine using ultra high performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) was developed. Urine sample (2 mL) were deconjugated by β-glucuronidase/arylsulfatase, extracted and cleaned using anion-exchange solid phase extraction cartridge and concentrated to 0.5 mL under gentle stream of nitrogen. The target analytes were separated on Waters Acquity UPLC BEH C₁₈ Column (100 mm×2.1 mm,1.7 μm), and eluted with 0.05% (V/V) acetic acid in water and 0.05% (V/V) acetic acid in acetonitrile in gradient. The target analytes were ionized in negative electrospray ionization (ESI-) mode and scanned under a multiple reaction monitoring (MRM) mode. Quantitative analysis of target analytes in urine was achieved by isotope labelled standard assay. In the range of 0.01-50 ng/mL, all four target analytes exhibited good linearity with correlation coefficients (r) above 0.9996. The method detection limits (MDLs) and method quantification limits (MQLs) were 0.01-0.03 ng/mL and 0.03-0.10 ng/mL, respectively. The recoveies were from 74% to 124%, with the relative standard deviations (RSD) between 1.2% and 15.0%. The intra-day and inter-day precisions were 3.5%-6.2% and 6.9%-9.8%, respectively. The developed method was performed to determinate the DINCH metabolites in 55 human urine samples collected in Beijing. All four DINCH metabolites were detected in urine, and the detected rates of MINCH, oxo-MINCH, OH-MINCH and cx-MINCH were 18.2%, 47.3%, 98.2% and 100%, respectively. The four metabolites were detected in the concentration ranges of
- Emerging plasticizer,
- Bio-monitoring,
- Urine,
- Internal exposure,
- Solid phase extraction
1. [1]
  HU Y, LIU C, WANG P, LI G, WANG A, CONG Y, LIANG X, LI W, ZHANG X, LI N. Ind. Eng. Chem. Res., 2020, 59(16):7367-7374.
2. [2]
  MALARVANNAN G, ONGHENA M, VERSTRAETE S, VAN PUFFELEN E, JACOBS A, VANHOREBEEK I, VERBRUGGEN S C A T, JOOSTEN K F M, VAN DEN BERGHE G, JORENS P G, COVACI A. J. Hazard. Mater., 2019, 363:64-72.
3. [3]
  BASF. https://www.basf.com/en/company/news-and-media/news-releases/2014/05/p-14-231.html.
4. [4]
  CARLOS K S, DE JAGER L S, BEGLEY T H. Food. Addit. Contam., Part A, 2018, 35(6):1214-1222.
5. [5]
  PLICHTA V, VÖLKEL W, FEMBACHER L, WÖCKNER M, NOWAK D, FROMME H. Toxicol. Lett., 2022, 355:82-87.
6. [6]
  EDWARDS L, MCCRAY N L, VANNOY B N, YAU A, GELLER R J, ADAMKIEWICZ G, ZOTA A R. J. Exposure Sci. Environ. Epidemiol., 2022, 32(3):366-373.
7. [7]
  NAGORKA R, KOSCHORRECK J. Environ. Pollution., 2020, 262:114237.
8. [8]
  BOOR B E, LIANG Y, CRAIN N E, JÄRNSTRÖM H, NOVOSELAC A, XU Y. Environ. Sci. Technol. Lett., 2015, 2(4):89-94.
9. [9]
  VASCONCELOS A L, SILVA M J, LOURO H. J. Toxicol. Environ. Health, Part A, 2019, 82(9):526-536.
10. [10]
  SCHAFFERT A, ARNOLD J, KARKOSSA I, BLÜHER M, VON BERGEN M, SCHUBERT K. Cells, 2021, 10(9):2367.
11. [11]
  CAMPIOLI E, LAU M, PAPADOPOULOS V. Environ. Res., 2019, 179:108773.
12. [12]
  ENGEL A, BUHRKE T, KASPER S, BEHR A C, BRAEUNING A, JESSEL S, SEIDEL A, VÖLKEL W, LAMPEN A. Toxicol. Lett., 2018, 287:83-91.
13. [13]
  YLAND J J, ZHANG Y, WILLIAMS P L, MUSTIELES V, VAGIOS S, SOUTER I, CALAFAT A M, HAUSER R, MESSERLIAN C. Environ. Pollution., 2022, 292:118476.
14. [14]
  LONG S E, KAHN L G, TRASANDE L, JACOBSON M H. Sci. Total Environ., 2021, 769:144560.
15. [15]
  VAN'T ERVE T J, ROSEN E M, BARRETT E S, NGUYEN R H, SATHYANARAYANA S, MILNE G L, CALAFAT A M, SWAN S H, FERGUSON K K. Environ. Sci. Technol., 2019, 53(6):3258-3267.
16. [16]
  SCHÜTZE A, OTTER R, MODICK H, LANGSCH A, BRÜNING T, KOCH H M. Arch Toxicol., 2017, 91(1):179-188.
17. [17]
  SILVA M J, FURR J, PREAU JR J L, SAMANDAR E, GRAY L E, CALAFAT A M. J. Exposure Sci. Environ. Epidemiol., 2012, 22(2):204-211.
18. [18]
  LEE G, KIM S, KHO Y, KIM S, LEE S, CHOI G, PARK J, WORAKHUNPISET S, MOON H B, OKANURAK K, GEOUNUPPAKUL M, TANGTITAWONG J, WETSUTTHANON K, TRISURAT D, CHOI K. Sci. Total Environ., 2020, 711:134822.
19. [19]
  GKRILLAS A, DIRVEN H, PAPADOPOULOU E, ANDREASSEN M, HJERTHOLM H, HUSØY T. Environ. Int., 2021, 155:106598.
20. [20]
  SCHÜTZE A, PÄLMKE C, ANGERER J, WEISS T, BRÜNING T, KOCH H M. J. Chromatogr. B, 2012, 895:123-130.
21. [21]
  PUBLIC HEALTH AGENCY OF CANADA. 2018, https://www.canada.ca/en/health-canada/services/environmentalworkplace-health/reports-publications/environmental-contaminants/fifth-report-human-biomonitoring.html#s5-7-3.
22. [22]
  CAO Z, LIN S, ZHAO F, LV Y, QU Y, HU X, YU S, SONG S, LU Y, YAN H, LIU Y, DING L, ZHU Y, LIU L, ZHANG M, WANG T, ZHANG W, FU H, JIN Y, CAI J, ZHANG X, YAN C, JI S, ZHANG Z, DAI J, ZHU H, GAO L, YANG Y, LI C, ZHOU J, YING B, ZHENG L, KANG Q, HU J, ZHAO W, ZHANG M, YU X, WU B, ZHENG T, LIU Y, BARRY RYAN P, BARR D B, QU W, ZHENG Y, SHI X. Environ. Int., 2021, 146:106252.
23. [23]
24. [24]
25. [25]
26. [26]
  LI J, ZHANG X, MU Y, HE Y, QIU T, LI W, ZENG L. J. Chromatogr. A, 2021, 1643:462079.
27. [27]
  United States Environmental Protection Agency. 2016, https://www.epa.gov/sites/default/files/2016-12/documents/mdlprocedure_rev2_12-13-2016.pdf.
1. [1]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
2. [2]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
3. [3]
  Jing SU , Bingrong LI , Yiyan BAI , Wenjuan JI , Haiying YANG , Zhefeng Fan . Highly sensitive electrochemical dopamine sensor based on a highly stable In-based metal-organic framework with amino-enriched pores. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1337-1346. doi: 10.11862/CJIC.20230414
4. [4]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
5. [5]
  Gaoyan Chen , Chaoyue Wang , Juanjuan Gao , Junke Wang , Yingxiao Zong , Kin Shing Chan . Heart to Heart: Exploring Cardiac CT. University Chemistry, 2024, 39(9): 146-150. doi: 10.12461/PKU.DXHX202402011
6. [6]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
7. [7]
  Shanying Chen , Kangning Huo , Ke Qi , Jingyi Li , Shuxin Li , Yunchao Li . A Novel Colloid Electrophoresis Experiment with the Characteristics of Resource Recycling and Inquiry-Driven Experimental Design. University Chemistry, 2024, 39(5): 274-286. doi: 10.3866/PKU.DXHX202311067
8. [8]
  Siming Bian , Sijie Luo , Junjie Ou . Application of van Deemter Equation in Instrumental Analysis Teaching: A New Type of Core-Shell Stationary Phase. University Chemistry, 2025, 40(3): 381-386. doi: 10.12461/PKU.DXHX202406087
9. [9]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
10. [10]
  . . Chinese Journal of Inorganic Chemistry, 2024, 40(12): 0-0.
11. [11]
  Hongbo Zhang , Yihong Tang , Suxia Zhang , Yuanting Li . Electrochemical Monitoring of Photocatalytic Degradation of Phenol Pollutants: A Recommended Comprehensive Analytical Chemistry Experiment. University Chemistry, 2024, 39(6): 326-333. doi: 10.3866/PKU.DXHX202310013
12. [12]
  Lingbang Qiu , Jiangmin Jiang , Libo Wang , Lang Bai , Fei Zhou , Gaoyu Zhou , Quanchao Zhuang , Yanhua Cui . 原位电化学阻抗谱监测长寿命热电池Nb₁₂WO₃₃正极材料的高温双放电机制. Acta Physico-Chimica Sinica, 2025, 41(5): 100040-. doi: 10.1016/j.actphy.2024.100040
13. [13]
  Changwei Dun , Xijun Zhang , Qianyi Zhao , Yuming Guo . Promoting the Construction of the Chemical Experiment Teaching Center and Forging a New Era in Cultivating Innovative Talents. University Chemistry, 2024, 39(7): 211-217. doi: 10.12461/PKU.DXHX202405139
14. [14]
  Xiaofeng Xia , Jielian Zhu . Innovative Comprehensive Experimental Design: Synthesis of 6-Fluoro-N-benzoyl Tetrahydroquinoline. University Chemistry, 2024, 39(10): 344-352. doi: 10.12461/PKU.DXHX202405063
15. [15]
  Xiaowu Zhang , Pai Liu , Qishen Huang , Shufeng Pang , Zhiming Gao , Yunhong Zhang . Acid-Base Dissociation Equilibrium in Multiphase System: Effect of Gas. University Chemistry, 2024, 39(4): 387-394. doi: 10.3866/PKU.DXHX202310021
16. [16]
  Chunai Dai , Yongsheng Han , Luting Yan , Zhen Li , Yingze Cao . Ideological and Political Design of Solid-liquid Contact Angle Measurement Experiment. University Chemistry, 2024, 39(2): 28-33. doi: 10.3866/PKU.DXHX202306065
17. [17]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
18. [18]
  Shijie Li , Ke Rong , Xiaoqin Wang , Chuqi Shen , Fang Yang , Qinghong Zhang . Design of Carbon Quantum Dots/CdS/Ta₃N₅ S-Scheme Heterojunction Nanofibers for Efficient Photocatalytic Antibiotic Removal. Acta Physico-Chimica Sinica, 2024, 40(12): 2403005-. doi: 10.3866/PKU.WHXB202403005
19. [19]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
20. [20]
  Haitang WANG , Yanni LING , Xiaqing MA , Yuxin CHEN , Rui ZHANG , Keyi WANG , Ying ZHANG , Wenmin WANG . Construction, crystal structures, and biological activities of two Ln^Ⅲ₃ complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1811)
HTML views(217)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142