Crystallization of Vanillin Isomers in Carboxymethyl Chitosan Gels

被引:0
作者
Zhang, Lin [1 ]
Lu, Xiaoling [1 ]
Li, Hao [1 ]
Chen, Hongjie [1 ,2 ]
Yin, Qi [1 ]
Hu, Xuehan [1 ]
Yang, Kang [1 ]
Yang, Fang [1 ]
Chen, Liya [1 ]
Yang, Zeng [1 ,2 ]
Long, You [1 ]
Shen, Chao [1 ]
Yao, Bo [1 ]
Huang, Chenghong [1 ]
机构
[1] Chongqing Univ Sci & Technol, Sch Chem & Chem Engn, Chongqing 401331, Peoples R China
[2] Chongqing Vocat Coll Light Ind, Sch Pharm & Nursing, Chongqing 401329, Peoples R China
关键词
CMCS; vanillin isomers; crystallization; IN-VITRO; SEPARATION; NUCLEATION; KINETICS; GROWTH;
D O I
10.3390/gels11040285
中图分类号
O63 [高分子化学(高聚物)];
学科分类号
070305 ; 080501 ; 081704 ;
摘要
The medicinal value of vanillin and its isomers has not been well developed, so it is necessary to prepare crystals of vanillin and its isomers as well as to investigate their crystallization rules in detail using advanced crystallization techniques in polymer gel. Based on molecular simulation, the maximum number of hydrogen bonds between CMCS with Van, IsoVan and oVan were reached at molar ratios of 1:9 and 1:4 and 1:5, respectively. The gel hardness and apparent viscosity of CMCS/Van isomers were proportional to the mole ratio, while elongation at break and tensile strength decreased with an increase in molar concentration depending on the position of the side chain group of the Van isomer, exposure of the benzene ring, steric resistance and the number of hydrogen bonds formed. The crystallization of Van, IsoVan and oVan in CMCS gel unexceptionally follow classical supersaturation theory in the case that nVan mainly exhibits a unique growth pattern from needle to strip, IsoVan's growth style changes from plate to bulk and oVan adapts growth pattern from needle to branch bifurcating. It was also found that the Van crystal changed from II-type to I-type under long-term heating. Studies have further confirmed that the discrepancy of physicochemical characteristics of CMCS/Van blend gel can be attributed to differences in the number of hydrogen bonds compared to CMCS with given group positions of Van isomers. This study provides powerful technical support for the gel crystallization of van isomers.
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页数:13
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共 43 条
[1]   Pharmacokinetics of Vanillin and its Effects on Mechanical Hypersensitivity in a Rat Model of Neuropathic Pain [J].
Beaudry, Francis ;
Ross, Andreanne ;
Lema, Pablo Patricio ;
Vachon, Pascal .
PHYTOTHERAPY RESEARCH, 2010, 24 (04) :525-530
[2]   Preparation and characterization of hydrogels obtained from chitosan and carboxymethyl chitosan [J].
Borges Ladeira, Natalia Maria ;
Donnici, Claudio Luis ;
de Mesquita, Joao Paulo ;
Pereira, Fabiano Vargas .
JOURNAL OF POLYMER RESEARCH, 2021, 28 (09)
[3]   Effect of vanillin and ethyl vanillin on cytochrome P450 activity in vitro and in vivo [J].
Chen, Xiao-min ;
Wei, Min ;
Zhang, Hai-mou ;
Luo, Cheng-hao ;
Chen, Yi-kun ;
Chen, Yong .
FOOD AND CHEMICAL TOXICOLOGY, 2012, 50 (06) :1897-1901
[4]   Conformational equilibria in vanillin and ethylvanillin [J].
Cocinero, Emilio J. ;
Lesarri, Alberto ;
Ecija, Patricia ;
Grabow, Jens-Uwe ;
Fernandez, Jose A. ;
Castano, Fernando .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2010, 12 (39) :12486-12493
[5]   Gel-Induced Selective Crystallization of Polymorphs [J].
Diao, Ying ;
Whaley, Kristen E. ;
Helgeson, Matthew E. ;
Woldeyes, Mahlet A. ;
Doyle, Patrick S. ;
Myerson, Allan S. ;
Hatton, T. Alan ;
Trout, Bernhardt L. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) :673-684
[6]   Structural determination of vanillin, isovanillin and ethylvanillin by means of gas electron diffraction and theoretical calculations [J].
Egawa, Toru ;
Kameyama, Akiyo ;
Takeuchi, Hiroshi .
JOURNAL OF MOLECULAR STRUCTURE, 2006, 794 (1-3) :92-102
[7]   Anticancer potential of isovanillin-based symmetrical azine: Synthesis, structure, molecular modeling, in silico leukemia inhibition and MD simulation [J].
Fadli, Khadidja ;
Bouchama, Abdelaziz ;
Tabbiche, Abdelkader ;
Chiter, Chaabane ;
Cornia, Andrea ;
Kumar, Neeraj ;
Yahiaoui, Messaoud ;
Zaidi, Farouk .
JOURNAL OF MOLECULAR STRUCTURE, 2024, 1312
[8]   Kinetics of vanillin production from om Kraft lignin oxidation [J].
Fargues, C ;
Mathias, A ;
Rodrigues, A .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 1996, 35 (01) :28-36
[9]   Antimicrobial and antioxidant activities of amines derived from vanillin as potential preservatives: Impact of the substituent chain length and polarity [J].
Fayeulle, Antoine ;
Trudel, Elodie ;
Damiens, Audrey ;
Josse, Alexandra ;
Youssef, Nesrine Ben Hadj ;
Vigneron, Pascale ;
Vayssade, Muriel ;
Rossi, Claire ;
Ceballos, Claire .
SUSTAINABLE CHEMISTRY AND PHARMACY, 2021, 22
[10]   The role of amide groups in the mechanism of acid-induced pectin gelation: A potential pH-sensitive hydrogel based on hydrogen bond interactions [J].
Feng, Shuhan ;
Yi, Jianyong ;
Ma, Youchuan ;
Bi, Jinfeng .
FOOD HYDROCOLLOIDS, 2023, 141