Citation: Jian-Feng LI, Li-Min LIAO. Structural Characterization and Retention Time Simulation of Allergenic Fragrances[J]. Chinese Journal of Structural Chemistry, ;2020, 39(10): 1753-1762. doi: 10.14102/j.cnki.0254–5861.2011–2727 shu

Structural Characterization and Retention Time Simulation of Allergenic Fragrances

Jian-Feng LI ^a ,
Li-Min LIAO ^{a, b,,}

a.
College of Chemistry and Chemical Engineering, Neijiang Normal University, Neijiang 641100, China
b.
Key Laboratory of Fruit Waste Treatment and Resource Recycling, Neijiang 641100, China

Corresponding author: Li-Min LIAO, liaolimin523@126.com
Received Date: 4 January 2020
Accepted Date: 12 February 2020

Fund Project: the Youth Foundation of Sichuan Provincial Department of Education 18ZB0323

Figures(8)

By classifying non-hydrogen atoms of organic compounds, parametric dyeing, and establishing the relationship between non-hydrogen atoms, new structure descriptors were obtained. The structures of 48 common allergenic fragrance organic compounds were parametrically characterized. The multiple linear regression (MLR) and partial least-squares regression (PLS) methods were used to build two models of relationship between the compound structure and chromatographic retention time. The stability of the models was evaluated by the "leave-one-out" cross test, and the predictive ability of the models was tested using an external sample set. The correlation coefficients (R²) of the two models are 0.9791 and 0.9744, those (R_CV²) of the cross test are 0.8542 and 0.7464, and those (R_test²) of the external prediction are 0.9802 and 0.9367, indicating that the models built have good fitting ability, stability and external forecasting capabilities. The structural factors affecting the chromatographic retention time of the compounds were analyzed. The results show that the compound with more secondary carbon atoms may have larger chromatographic retention time (t_R) value. This paper has certain reference value for the study on the relationship between the structures and properties of allergenic fragrance organic compounds.
- allergenic fragrance,
- structure descriptor,
- structure characterization,
- simulation prediction
1. [1]
  Cheng, Y.; Wang, C.; Xue, Y. M.; Chen, W.; Wang, X.; Bai, H.; Cai, T. P.; Hu, K. X. Determination of dicumarol and cyclocoumarol in cosmetics by HPLC/DAD. J. Anal. Test. 2008, 27, 1996–1999.
2. [2]
  Xi, H. W.; Ma, Q.; Liu, Q.; Wang, Y.; Ding, L; Su, N.; Bai, H.; Wang, C. HPLC-MS/MS determination of nonylphenol in cosmetics. J. Instrumental Anal. 2010, 29, 46–50.
3. [3]
  Jiang, J. H.; Chen, S.; Xie, J. X. Analysis of ten harmful fragrances in cosmetics by GC/FTIR. Chin. J. Health Lab. Technol. 2005, 15, 1415–1418.
4. [4]
  Li, Z. Y.; Wei, S. W.; Zhu, Z. J.; Jin, J. L. Determination of odorous substances in textile by solvent extraction GC-MS. Chem. Anal. Meterage 2011, 20, 35–37.
5. [5]
  Gu, J. H.; Pan, K.; Liu, Y.; Zhu, Z. H. Determination of eugenol in fragrant fabrics by GC/MS method. Chin. Dyeing Finishing 2014, 40, 40–45.
6. [6]
  Gao, M. X.; Wang, X. Y.; Gong, Y.; Wang, H.; Liao, Q. Detection of nonanal aromatic in coated fabrics by headspace gas chromatography-mass spectrometry. Anal. Instr. 2011, 42, 32–35.
7. [7]
  Wu, X. H.; Zhu, R. Z.; Lu, S. M.; Wang, K.; Meng Z. J.; Mou, D. R.; Miao, M. M. UHPLC-MS/MS determination of coumarin in essence. Phys. Test Chem. Anal. Part B: Chem. Anal. 2000, 5, 1407–1400.
8. [8]
  Wei, B. W.; Dai, X. W.; Yang, L.; Yang, R. J. Determination of fragrance allergens in toys by gas chromatography-ion trap mass spectrometry. Enciron. Chem. 2013, 32, 2406–2410.
9. [9]
  Chen, L. Q.; Lin, Z. H.; Xing, Y. N.; Feng, A. H.; Wang, X.; Chen, Z. Y. Determination of fragrance allergens in toys by gas chromatography-mass spectrometry. Chin. J. Anal. Lab. 2014, 33, 1171–1176.
10. [10]
  Li, H. Y.; Bai, H.; Lv, Q.; Li, P.; Wang, X.; Guo, X. Y.; Zhang, Q. A method for fast screening of allergenic fragrance substance in plushtoys. Chin. J. Anal. Chem. 2013, 41, 1518–1525.
11. [11]
  Baviskar, B. A.; Deore, S. L.; Alone, S. 2D QSAR study on saponins of pulsatilla koreana as an anticancer agent. Pharm. Commun. 2019, 9, 2–6.
12. [12]
  Abdel-Aziz, H. A.; Eldehna, W. M.; Fares, M.; Al-Rashood, S. T. A.; Al-Rashood, K. A.; Abdel-Aziz, M. M.; Soliman, D. H. Synthesis, biological evaluation and 2D-QSAR study of halophenyl bis-hydrazones as antimicrobial and, antitubercular agents. Int. J. Mol. Sci. 2015, 16, 8719–8743. doi: 10.3390/ijms16048719
13. [13]
  Khan, K.; Khan, P. M.; Lavado, G.; Valsecchi, C.; Pasqualini, J.; Baderna, D.; Marzo, M.; Lombardo, A.; Roy, K.; Benfenati, E. QSAR modeling of daphnia magna and fish toxicities of biocides using 2D descriptors. Chemosphere 2019, 229, 8–17. doi: 10.1016/j.chemosphere.2019.04.204
14. [14]
  Yu, W.; He, H. M.; Feng, C. J. QSAR models for the inhibitory enzyme activities of triazinyl-oxadiazolyl-pyrazole derivatives. Chemistry 2018, 81, 636–640. doi: 10.7524/j.issn.0254-6108.2017102301
15. [15]
  Cai, W. P.; Wei, X. C.; Zheng, C.; He, L.; Zhao, W. Z.; Zheng, X. A 3D-QSAR model of the tyrosinase inhibitory activity of curcumin analogues. Mod. Food Sci. Technol. 2017, 33, 41–50.
16. [16]
  Kaur, M.; Silakari, O. Ligand-based and e-pharmacophore modeling, 3D-QSAR and hierarchical virtual screening to identify dual inhibitors of spleen tyrosine kinase (Syk) and janus kinase 3 (JAK3). J. Biomol. Struct. Dyn. 2017, 35, 1–18. doi: 10.1080/07391102.2015.1136896
17. [17]
  Chen, Y. Z.; Fan, X. J.; Zhang, H.; Liang, G. Z.; Liu, B. G. 3D-QSAR and interaction mechanism of flavonoids as aldose reductase inhibitors based on topomer Comfa and surflex-dock. J. Henan Univ. Technol. (Nat. Sci. Ed. ) 2018, 39, 91–96.
18. [18]
  Misra, S.; Singh, H.; Kim, K.; Perez-Sanchez, H. S.; Kim, M.; Kumar, S.; Yadav, D. K.; Jang, C.; Choi, E. H.; Mancera, R. L.; Sharma, P. Studies of the benzopyran class of selective COX-2 inhibitors using 3D-QSAR and molecular docking. Arch. Pharmacal Res. 2018, 41, 1178–1189 doi: 10.1007/s12272-017-0945-7
19. [19]
  Cui, S. H.; Niu, Z. Y.; Zhang, X. M.; Qin, L. Y.; Luo, X. Determination of 48 fragrance allergens in plastic toys by gas chromatography-mass spectrometry. J. Chin. Mass Spectrom. Soc. 2016, 37, 163–172.
20. [20]
  Li, J. F.; Xie, Y. H.; Lei, Y. H. Study on relationship of structure and change in heat capacity for some polymers. Compu. Appl. Chem. 2016, 33, 833–837.
21. [21]
  Li, J. F. Study on acute toxicity for halogenated phenols by using molecular vertex electronegativity interaction vector. Comput. Appl. Chem. 2015, 32, 1399–1403.
22. [22]
  Liao, L. M. Research on structure-retention index relationship of aldehydes and ketones. Chem. Res. Appl. 2015, 27, 617–623.
23. [23]
  Liao, L. M.; Huang, X.; Lei, G. D. Structural characterization and octanol/water partition coefficient (LogP) prediction for oxygen-containing organic compounds. Chin. J. Struct. Chem. 2017, 36, 1243–1250.
24. [24]
  Qin, Z. L. A new connectivity index for QSPR/QSAR study of alcohol. J. Xuzhou Normal Univ. (Nat. Sci Ed. ) 2001, 19, 50–52.
25. [25]
  Du, X. H. Predicting the lgKow of PCDDs using novel topological parameter. J. Wuhan Univ. Technol. 2007, 29, 40–44.
26. [26]
  Chen, Y. Prediction of aqueous solubility, hydrophobic parameter for esters and ketones with novel valence connectivity index. J. Nanjing Univ. Technol. 2005, 27, 41–43.
27. [27]
  Xu, Qi; Fan, L. L.; Xu, J. A simple 2D-QSPR model for the prediction of setschenow constants of organic compounds. Maced. J. Chem. Chem. Eng. 2016, 35, 53–62.
28. [28]
  Gramatica, P.; Pilutti, P.; Papa, E. A tool for the assessment of VOC degradability by tropospheric oxidants starting from chemical structure. J. Chem. Inf. Comput. Sci. 2004, 44, 1794–1802.
29. [29]
  Andersson, P. M.; Sjstrom, M.; Lundstedt, T. Preprocessing peptides sequences for multivariate sequence-property analysis. Chemom. Intell. Lab. Syst. 1998, 42, 41–50.
30. [30]
  Liao, L. M.; Li, J. F.; Qing, D. H.; Lei, G. D. Structural characterization and retention time prediction for components of essential oil of meconopsis integrifolia flowers. Chin. J. Struct. Chem. 2010, 29, 1638–1645.
31. [31]
  Liao, L. M.; Zhu, J.; Li, J. F.; Lei, G. D. QSRR study on components of styrax japonicus sieb flowers using improved molecular electronegativity-distance vector (I-MEDV). Chin. J. Struct. Chem. 2011, 30, 105–110.
32. [32]
  Zhu, W. P.; Mei, H.; Shu, M.; Liao, L. M.; Yang, J.; Li, Z. L. Structural characterization of some components from essential oils of rosa banksiae ait for estimation and prediction of their linear retention index and retention times. Chin. J. Chin. Mater. Med. 2008, 33, 609–611.
1. [1]
  Liping GUO . Synthesis and crystal structure characterization of yttrium imido complex: The reactivity of 2-substituted-1-amino-o-carborane with yttrium dialkyl complex. Chinese Journal of Inorganic Chemistry, 2025, 41(7): 1409-1415. doi: 10.11862/CJIC.20250065
2. [2]
  Teng-Yu Huang , Junliang Sun , De-Xian Wang , Qi-Qiang Wang . Recent progress in chiral zeolites: Structure, synthesis, characterization and applications. Chinese Chemical Letters, 2024, 35(12): 109758-. doi: 10.1016/j.cclet.2024.109758
3. [3]
  Run-Han Li , Tian-Yi Dang , Wei Guan , Jiang Liu , Ya-Qian Lan , Zhong-Min Su . Evolution exploration and structure prediction of Keggin-type group IVB metal-oxo clusters. Chinese Chemical Letters, 2024, 35(5): 108805-. doi: 10.1016/j.cclet.2023.108805
4. [4]
  Lu Li , Jianing Shen , Qinkun Xiao , Chaozheng He , Jinzhou Zheng , Chaoqin Chu , Chen Chen . Stable crystal structure prediction using machine learning-based formation energy and empirical potential function. Chinese Chemical Letters, 2025, 36(11): 110421-. doi: 10.1016/j.cclet.2024.110421
5. [5]
  Linghai Han , Xue Gong , Yupeng Wang , Dan Wang , Chunyu Ru , Xian Wang , Donglai Guo , Fangbing Liu , Xia Sheng , Junjie Ge . Structure, design, and advanced characterization techniques of catalyst layers in proton exchange membrane fuel cells. Chinese Chemical Letters, 2026, 37(10): 111432-. doi: 10.1016/j.cclet.2025.111432
6. [6]
  Zhaodong WANG . In situ synthesis, crystal structure, and magnetic characterization of a trinuclear copper complex based on a multi-substituted imidazo[1,5-a]pyrazine scaffold. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 597-604. doi: 10.11862/CJIC.20240268
7. [7]
  Xinzhe ZHANG , Jiarong XU , Mochou GAO , Yage LIU , Yanbao ZHAO , Jingzeng CUI , Xueyan ZOU . Silver chloride/chitosan-based chloramine nanohybrid with excellent antibacterial activity: Design and structure characterization as well as Ag⁺-Cl^- synergistic antibacterial effect. Chinese Journal of Inorganic Chemistry, 2026, 42(2): 428-438. doi: 10.11862/CJIC.20250123
8. [8]
  Yao Zou , Difei Gong , Haiguang Yang , Hongmei Yu , Guorong He , Ningbo Gong , Lianhua Fang , Guanhua Du , Yang Lu . Prediction, screening, characterization, antioxidant and antihypoxic effects of multi-component zwitterionic cocrystals of dietary flavonoids with picolinic acid. Chinese Chemical Letters, 2025, 36(9): 110768-. doi: 10.1016/j.cclet.2024.110768
9. [9]
  Chao Ma , Cong Lin , Jian Li . MicroED as a powerful technique for the structure determination of complex porous materials. Chinese Journal of Structural Chemistry, 2024, 43(3): 100209-100209. doi: 10.1016/j.cjsc.2023.100209
10. [10]
  Yuhang Li , Yang Ling , Yanhang Ma . Application of three-dimensional electron diffraction in structure determination of zeolites. Chinese Journal of Structural Chemistry, 2024, 43(4): 100237-100237. doi: 10.1016/j.cjsc.2024.100237
11. [11]
  Hai-Ling Wang , Zhong-Hong Zhu , Hua-Hong Zou . Structure and assembly mechanism of high-nuclear lanthanide-oxo clusters. Chinese Journal of Structural Chemistry, 2024, 43(9): 100372-100372. doi: 10.1016/j.cjsc.2024.100372
12. [12]
  Jie Ma , Jianxiang Wang , Jianhua Yuan , Xiao Liu , Yun Yang , Fei Yu . The regulating strategy of hierarchical structure and acidity in zeolites and application of gas adsorption: A review. Chinese Chemical Letters, 2024, 35(11): 109693-. doi: 10.1016/j.cclet.2024.109693
13. [13]
  Guilong Li , Wenbo Ma , Jialing Zhou , Caiqin Wu , Chenling Yao , Huan Zeng , Jian Wang . A composite hydrogel with porous and homogeneous structure for efficient osmotic energy conversion. Chinese Chemical Letters, 2025, 36(2): 110449-. doi: 10.1016/j.cclet.2024.110449
14. [14]
  Fadeng Yang , Pengli Zhang , Jianbo Liu , Chuan Wan , Jinming Sun , Chuan Dai , Zhihong Liu , Yuhao An , Yujie Wu , Yun Xing , Feng Yin , Yuxin Ye , Wei Han , Zigang Li . Self-assembly of a cyclo-pentapeptide with a novel frame structure. Chinese Chemical Letters, 2025, 36(9): 110785-. doi: 10.1016/j.cclet.2024.110785
15. [15]
  Aoran LIU , Rui LI , Zongyao WANG , Penghui SHANG , Jiawei WAN , Dan WANG . Hollow multi-shelled structure materials for catalytic applications. Chinese Journal of Inorganic Chemistry, 2025, 41(10): 2039-2053. doi: 10.11862/CJIC.20250036
16. [16]
  Zihe SONG , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Crystal structure, thermal analysis, and luminescence properties of six heterocyclic lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 181-192. doi: 10.11862/CJIC.20250126
17. [17]
  Yaofei Zhang , Jiani Chen , Haotian Hu , Jianghua Huang , Jiafeng Wei , Fukun Bi , Xiaodong Zhang . Impact of residual ions on catalyst structure and catalytic performance: A review. Chinese Chemical Letters, 2026, 37(3): 111549-. doi: 10.1016/j.cclet.2025.111549
18. [18]
  Ruijing Fu , Bin Xiao , Haoyuan Weng , Pan Wang , Guangxia Wang , Qingguang Zeng , Dawei Wen , Guanjun Xiao . An optical pressure sensing phosphor of high-sensitivity by soft structure. Chinese Chemical Letters, 2026, 37(3): 111916-. doi: 10.1016/j.cclet.2025.111916
19. [19]
  Zhengzheng LIU , Pengyun ZHANG , Chengri WANG , Shengli HUANG , Guoyu YANG . Synthesis, structure, and electrochemical properties of a sandwich-type {Co₆}-cluster-added germanotungstate. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1173-1179. doi: 10.11862/CJIC.20240039
20. [20]
  Xiaoxia WANG , Ya'nan GUO , Feng SU , Chun HAN , Long SUN . Synthesis, structure, and electrocatalytic oxygen reduction reaction properties of metal antimony-based chalcogenide clusters. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1201-1208. doi: 10.11862/CJIC.20230478

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(1817)
HTML views(78)

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