[1]
|
Martău, G.A., Călinoiu, L.-F. and Vodnar, D.C. (2021) Bio-Vanillin: Towards a Sustainable Industrial Production. Trends in Food Science & Technology, 109, 579-592. https://doi.org/10.1016/j.tifs.2021.01.059
|
[2]
|
Hsueh, S.S., Lu, J.H., Wu, J.W., Lin, T.H. and Wang, S.S. (2021) Protection of Human γD-Crystallin Protein from Ultraviolet C-Induced Aggregation by Ortho-Vanillin. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 261, Article ID: 120023. https://doi.org/10.1016/j.saa.2021.120023
|
[3]
|
Shakeel, F., Haq, N., Raish, M., Siddiqui, N.A., Alanazi, F.K. and Alsarra, I.A. (2016) Antioxidant and Cytotoxic Effects of Vanillin via Eucalyptus Oil Containing Self-Nanoemulsifying Drug Delivery System. Journal of Molecular Liquids, 218, 233-239. https://doi.org/10.1016/j.molliq.2016.02.077
|
[4]
|
Sarkar, M.K., Kar, A., Jayaraman, A., Kar Mahapatra, S. and Vadivel, V. (2021) Pharmacokinetic Properties and Anti-Proliferative Mechanisms of Vanillin against Acute Lympho-blastic Leukemia (Jurkat) Cells. South African Journal of Botany, 142, 82-87. https://doi.org/10.1016/j.sajb.2021.06.016
|
[5]
|
González-Baró, A.C., Pis-Diez, R., Parajón-Costa, B.S. and Rey, N.A. (2012) Spectroscopic and Theoretical Study of the O-Vanillin Hydrazone of the Mycobactericidal Drug Isoniazid. Journal of Molecular Structure, 1007, 95-101.
https://doi.org/10.1016/j.molstruc.2011.10.026
|
[6]
|
Ma, W., Zhang, Q., Li, X., Ma, Y., Liu, Y., Hu, S., et al. (2020) IPM712, a Vanillin Derivative as Potential Antitumor Agents, Displays Better Antitumor Activity in Colorectal Cancers Cell Lines. European Journal of Pharmaceutical Sciences, 152, Article ID: 105464. https://doi.org/10.1016/j.ejps.2020.105464
|
[7]
|
Alhalaweh, A., George, S., Basavoju, S., Childs, S.L., Rizvi, S.A.A. and Velaga, S.P. (2012) Pharmaceutical Cocrystals of Nitrofurantoin: Screening, Characterization and Crystal Structure Analysis. CrystEngComm, 14, 5078-5088.
https://doi.org/10.1039/c2ce06602e
|
[8]
|
Mccrone, W.C. (1950) Crystallographic Data 28. Vanillin I (3-Methoxy-4-Hydroxybenzaldehyde). Analytical Chemistry, 22, 500. https://doi.org/10.1021/ac60039a044
|
[9]
|
Robinson, R.A. and Kiang, A.K. (1955) The Ionization Constants of Vanillin and Two of Its Isomers. Transactions of the Faraday Society, 51, 1398-1402. https://doi.org/10.1039/tf9555101398
|
[10]
|
Hussain, K., Thorsen, G. and Malthe-Srenssen, D. (2001) Nucleation and Metastability in Crystallization of Vanillin and Ethyl Vanillin. Chemical Engineering Science, 56, 2295-2304. https://doi.org/10.1016/S0009-2509(00)00438-3
|
[11]
|
Cocinero, E.J., Lesarri, A., Ecija, P., Grabow, J.U., Fernán-dez, J.A. and Castaño, F. (2010) Conformational Equilibria in Vanillin and Ethylvanillin. Physical Chemistry Chemical Physics, 12, 12486-12493.
https://doi.org/10.1039/c0cp00585a
|
[12]
|
Kavuru, P., Grebinoski, S.J., Patel, M.A., Wojtas, L. and Chadwick, K. (2016) Polymorphism of Vanillin revisited: The Discovery and Selective Crystallization of a Rare Crystal Structure. CrystEngComm, 18, 1118-1122.
https://doi.org/10.1039/C5CE00568J
|
[13]
|
Singh, N.B., Henningsen, T., Metz, E.P.A., Hamacher, R., Cum-berledge, E., Hopkins, R.H. and Mazelsky, R. (1991) Solution Growth of Vanillin Single Crystals. Materials Letters, 12, 270-275.
https://doi.org/10.1016/0167-577X(91)90012-U
|
[14]
|
Sorensen, T.J. (2014) Oiling-Out and Crystallization of Vanillin from Aqueous Solutions. Chemical Engineering Technology, 37, 1959-1963. https://doi.org/10.1002/ceat.201400201
|
[15]
|
Yang, J., Xu, S., Wang, J. and Gong, J. (2020) Nucleation Behavior of Ethyl Vanillin: Balance between Chemical Potential Difference and Saturation Temperature. Journal of Molecular Liq-uids, 303, Article ID: 112609.
https://doi.org/10.1016/j.molliq.2020.112609
|
[16]
|
Sundareswaran, S. and Karuppannan, S. (2021) Nucleation Control and Separation of Vanillin Polymorphs I and II through the Swift Cooling Crystallization Process. CrystEngComm, 23, 1634-1642.
https://doi.org/10.1039/D0CE01557A
|
[17]
|
Sundareswaran, S. and Karuppannan S. (2020) Supersaturation De-pendent Separation of Vanillin Polymorphs from Aqueous Solution in the Presence of Ni-Foam as Template. Crystal Research and Technology, 55, 2000020.
https://doi.org/10.1002/crat.202000020
|
[18]
|
Kupka, A., Vasylyeva, V., Hofmann, D.W.M., Yusenko, K.V. and Merz, K. (2012) Solvent and Isotopic Effects on Acridine and Deuterated Acridine Polymorphism. Crystal Growth & Design, 12, 5966-5971.
https://doi.org/10.1021/cg300959w
|
[19]
|
Shibata, F., Yokota, M. and Doki, N. (2021) Thermodynamic Character-istics of L-Histidine Polymorphs and Effect of Ethanol on the Crystallization. Journal of Crystal Growth, 564, Article ID: 126086.
https://doi.org/10.1016/j.jcrysgro.2021.126086
|
[20]
|
Parambil, J.V., Poornachary, S.K., Tan, R.B.H. and Heng, J.Y.Y. (2017) Influence of Solvent Polarity and Supersaturation on Template-Induced Nucleation of Carbamazepine Crystal Polymorphs. Journal of Crystal Growth, 469, 84-90.
https://doi.org/10.1016/j.jcrysgro.2016.09.058
|
[21]
|
Garg, R.K. and Sarkar, D. (2016) Polymorphism Control of p-Aminobenzoic Acid by Isothermal Anti-Solvent Crystallization. Journal of Crystal Growth, 454, 180-185. https://doi.org/10.1016/j.jcrysgro.2016.09.023
|
[22]
|
Kaliwanda, M. 乙基香兰素结晶过程设计[D]: [硕士学位论文]. 天津: 天津大学, 2018.
|
[23]
|
Mao, H., Chen, H., Jin, M., Wang, C., Xiao, Z. and Niu, Y. (2020) Measurement and Correlation of Solubility of O-Vanillin in Different Pure and Binary Solvents at Temperatures from 273.15 K to 303.15 K. The Journal of Chemical Thermodynamics, 150, Article ID: 106199. https://doi.org/10.1016/j.jct.2020.106199
|
[24]
|
Lenka, M. and Sarkar, D. (2018) Improving Crystal Size Distribu-tion by Internal Seeding Combined Cooling/Antisolvent Crystallization with a Cooling/Heating Cycle. Journal of Crystal Growth, 486, 130-136.
https://doi.org/10.1016/j.jcrysgro.2018.01.029
|
[25]
|
Carletta, A., Dubois, J., Tilborg, A. and Wouters, J. (2015) Solid-State Investigation on a New Dimorphic Substituted N-Salicylidene Compound: Insights into Its Thermochromic Behaviour. CrystEngComm, 17, 3509-3518.
https://doi.org/10.1039/C5CE00283D
|
[26]
|
Digarse, H. and Sarkar, D. (2019) Production of the Metastable δ-Polymorphic form of Pyrazinamide by Isothermal Internal Seeding Anti-Solvent Crystallization. Journal of Crystal Growth, 526, Article ID: 125245.
https://doi.org/10.1016/j.jcrysgro.2019.125245
|
[27]
|
陆海东. 乙基香兰素结晶过程研究[D]: [硕士学位论文]. 北京: 北京化工大学, 2015.
|
[28]
|
Sudha, C. and Srinivasan, K. (2013) Supersaturation Dependent Nucleation Control and Separation of Mono, Ortho and Unstable Polymorphs of Paracetamol by Swift Cooling Crystallization Technique. CrystEngComm, 15, 1914-1921.
https://doi.org/10.1039/c2ce26681d
|
[29]
|
Brandel, C. and ter Horst, J.H. (2015) Measuring Induction Times and Crystal Nucleation Rates. Faraday Discussions, 179, 199-214. https://doi.org/10.1039/C4FD00230J
|
[30]
|
Sun, X., Garetz, B.A. and Myerson, A.S. (2006) Supersaturation and Polarization Dependence of Polymorph Control in the Nonphotochemical Laser-Induced Nucleation (NPLIN) of Aqueous Glycine Solutions. Crystal Growth & Design, 6, 684-689. https://doi.org/10.1021/cg050460+
|
[31]
|
赵海平. 香兰素结晶过程研究[D]: [硕士学位论文]. 天津: 天津大学, 2013.
|
[32]
|
Ouyang, J., Xing, X., Chen, J., Zhou, L., Zhou, L. and Heng, J.Y.Y. (2021) Effects of Solvent, Supersaturation Ratio and Silica Template on Morphology and Polymorph Evolution of Vanillin during Swift Cooling Crystallization. Particuology, 65, 93-104. https://doi.org/10.1016/j.partic.2021.09.003
|
[33]
|
Nanev, C.N., Saridakis, E., Govada, L., Kassen, S.C., Solomon, H.V. and Chayen, N.E. (2019) Hydrophobic Interface-Assisted Protein Crystal-lization: Theory and Experiment. ACS Applied Materials & Interfaces, 11, 12931-12940.
https://doi.org/10.1021/acsami.8b20995
|
[34]
|
De Poel, W., Elemans, J., Van Enckevort, W.J.P., Rowan, A.E. and Vlieg, E. (2019) Epitaxial Crystallization of Insulin on an Ordered 2D Polymer Template. Chemistry, 25, 3756-3760. https://doi.org/10.1002/chem.201805276
|
[35]
|
Banerjee, M., Saraswatula, S., Willows, L.G., Woods, H. and Brettmann, B. (2018) Pharmaceutical Crystallization in Surface-Modified Nanocellulose Organogels. Journal of Materi-als Chemistry B, 6, 7317-7328.
https://doi.org/10.1039/C8TB01554F
|
[36]
|
Harding, J.H., Freeman, C.L. and Duffy, D.M. (2014) Oriented Crystal Growth on Organic Monolayers. CrystEngComm, 16, 1430-1438. https://doi.org/10.1039/C3CE41677A
|
[37]
|
Al-Ani, A.J., Herdes, C., Wilson, C.C. and Castro-Dominguez, B. (2020) Engineering a New Access Route to Metastable Polymorphs with Electrical Confinement. Crystal Growth & De-sign, 20, 1451-1457.
https://doi.org/10.1021/acs.cgd.9b01100
|
[38]
|
Yao, C., Li, Y., Wang, L., Song, S., Liu, Y. and Tao, X. (2018) Tuning the Solution-Mediated Concomitant Phase Transformation Outcome of the Piroxicam Monohydrate by Two Hy-droxylcontaining Additives: Hydroxypropyl Cellulose and H2O. Crystal Growth & Design, 19, 583-590. https://doi.org/10.1021/acs.cgd.8b00936
|
[39]
|
Yan, Y., Chen, J.-M. and Lu, T.-B. (2015) Thermodynamics and Preliminary Pharmaceutical Characterization of Melatonin-Pimelic Acid Cocrystal Prepared by a Melt Crystallization Method. CrystEngComm, 17, 612-620.
https://doi.org/10.1039/C4CE01921K
|
[40]
|
Lotarev, S.V., Lipatiev, A.S., Lipateva, T.O., et al. (2021) Ultrafast Laser-Induced Crystallization of Lead Germanate Glass. Crystals, 11, Article No. 193. https://doi.org/10.3390/cryst11020193
|
[41]
|
Adrjanowicz, K., Paluch, M. and Richert, R. (2018) Formation of New Polymorphs and Control of Crystallization in Molecular Glass-Formers by Electric Field. Physical Chemistry Chemical Physics, 20, 925-931.
https://doi.org/10.1039/C7CP07352F
|
[42]
|
Karabanov, S.M., Suvorov, D.V., Tarabrin, D.Y., Slivkin, E.V. and Karabanov, A.S. (2021) Control of Direct Crystallization by a Running Magnetic Field. MRS Advances, 6, 619-624. https://doi.org/10.1557/s43580-021-00083-4
|
[43]
|
Sergeev, A., Shilkina, N., Motyakin M., Barashkova, I., Zabo-rova, V., Kanina, K., et al. (2021) Anhydrous Fat Crystallization of Ultrasonic Treated Goat Milk: DSC and NMR Re-laxation Studies. Ultrasonics Sonochemistry, 78, Article ID: 105751. https://doi.org/10.1016/j.ultsonch.2021.105751
|
[44]
|
Durant, S. and Karran, P. (2003) Vanillins—A Novel Family of DNA-PK Inhibitors. Nucleic Acids Research, 31, 5501-5512. https://doi.org/10.1093/nar/gkg753
|
[45]
|
Karakurt, I., Ozaltin, K., Vargun, E., Kucerova, L., Suly, P., Harea, E., et al. (2021) Controlled Release of Enrofloxacin by Vanil-lin-Crosslinked Chitosan-Polyvinyl Alcohol Blends. Materials Science and Engineering: C, 126, Article ID: 112125. https://doi.org/10.1016/j.msec.2021.112125
|
[46]
|
Raschip, I.E., Hitruc, E.G., Oprea, A.M., Popescu, M.-C. and Vasile, C. (2011) In Vitro Evaluation of the Mixed Xanthan/Lignin Hydrogels as Vanillin Carriers. Journal of Molecular Structure, 1003, 67-74.
https://doi.org/10.1016/j.molstruc.2011.07.023
|
[47]
|
Vasile, C., Dumitriu, R.P., Cheaburu, C.N. and Oprea, A.M. (2009) Architecture and Composition Influence on the Properties of Some Smart Polymeric Materials Designed as Ma-trices in Drug Delivery Systems. A Comparative Study. Applied Surface Science, 256, S65-S71. https://doi.org/10.1016/j.apsusc.2009.04.120
|
[48]
|
Kale, D.P., Zode, S.S. and Bansal, A.K. (2017) Challenges in Translational Development of Pharmaceutical Cocrystals. Journal of Pharmaceutical Sciences, 106, 457-470. https://doi.org/10.1016/j.xphs.2016.10.021
|
[49]
|
Yousef, M. and Vangala, V.R. (2019) Pharmaceutical Cocrystals: Molecules, Crystals, Formulations, Medicines. Crystal Growth & Design, 19, 7420-7438. https://doi.org/10.1021/acs.cgd.8b01898
|
[50]
|
Braga, D., Grepioni, F., Maini, L., Mazzeo, P.P. and Rubini, K. (2010) Solvent-Free Preparation of Co-Crystals of Phenazine and Acridine with Vanillin. Thermochimica Acta, 507-508, 1-8. https://doi.org/10.1016/j.tca.2010.04.021
|
[51]
|
Jacobs, A. and Amombo Noa, F.M. (2015) Co-Crystals and Co-Crystal Hydrates of Vanillic Acid. CrystEngComm, 17, 98-106. https://doi.org/10.1039/C4CE01795A
|
[52]
|
Buvaneswari, M., Santhakumari, R., Usha, C., Jayasree, R. and Sagadevan, S. (2021) Synthesis, Growth, Structural, Spectroscopic, Optical, Thermal, DFT, HOMO-LUMO, MEP, NBO Analysis and Thermodynamic Properties of Vanillin Isonicotinic Hydrazide Single Crystal. Journal of Molecular Structure, 1243, Article ID: 130856.
https://doi.org/10.1016/j.molstruc.2021.130856
|
[53]
|
Rajesh Thipparaboina, D.K., Mittapalli, S., Sridhar, B., Nan-gia, A. and Shastri, N. (2015) Ionic, Neutral and Hybrid Acid-Base Crystalline Adducts of Lamotrigine with Improved Pharmaceutical Performance. Crystal Growth & Design, 15, 5816-5826. https://doi.org/10.1021/acs.cgd.5b01187
|
[54]
|
Krishna, G.R., Shi, L., Bag, P.P., Sun, C.C. and Malla Reddy, C. (2015) Correlation among Crystal Structure, Mechanical Behavior, and Tabletability in the Co-Crystals of Vanillin Iso-mers. Crystal Growth & Design, 15, 1827-1832.
https://doi.org/10.1021/cg5018642
|
[55]
|
Sanphui, P., Goud, N.R., Khandavilli, U.B.R. and Nangia, A. (2011) Fast Dissolving Curcumin Cocrystals. Crystal Growth & Design, 11, 4135-4145. https://doi.org/10.1021/cg200704s
|
[56]
|
Braga, D. and Grepioni, F. (2005) Making Crystals from Crystals: A Green Route to Crystal Engineering and Polymorphism. Chemical Communications, No. 29, 3635-3645. https://doi.org/10.1039/b504668h
|
[57]
|
Tomadoni, B., Ponce, A., Pereda, M. and Ansorena, M.R. (2019) Vanillin as a Natural Cross-Linking Agent in Chitosan-Based Films: Optimizing Formulation by Response Surface Methodology. Polymer Testing, 78, Article ID: 105935.
https://doi.org/10.1016/j.polymertesting.2019.105935
|
[58]
|
Zbačnik, M., Vitković, M., Vulić, V., Nogalo, I. and Cinčić, D. (2016) Competition between Halogen Bonds in Cocrystals of Imines Derived from o-Vanillin. Crystal Growth & Design, 16, 6381-6389.
https://doi.org/10.1021/acs.cgd.6b01037
|
[59]
|
Marija Zbačnik, M.P., Stilinović, V., Vitković, M. and Cinčić, D. (2017) The Halogen Bonding Proclivity of the Ortho Methoxy-Hydroxy Group in Cocrystals of O-Vanillin Imines and Diiodotetrafluoro-Benzenes. CrystEngComm, 19, 5576-5582. https://doi.org/10.1039/C7CE01332A
|
[60]
|
Vinko Nemec, L.F., Vitasović, T. and Cinčić, D. (2019) Halogen Bonding of the Aldehyde Oxygen Atom in Cocrystals of Ar-omatic Aldehydes and 1,4-Diiodotetrafluorobenzene. CrystEngComm, 21, 3251-3255.
https://doi.org/10.1021/acs.jpclett.0c02371
|
[61]
|
Sun, G., Jin, Y., Li, S., Yang, Z., Shi, B., Chang, C., et al. (2020) Virtual Coformer Screening by Crystal Structure Predictions: Crucial Role of Crystallinity in Pharmaceutical Cocrystalli-zation. The Journal of Physical Chemistry Letters, 11, 8832-8838. https://doi.org/10.1021/acs.jpclett.0c02371
|
[62]
|
Zheng, L., Zhu, B., Wu, Z., Fang, X., Hong, M., Liu, G., et al. (2020) Strategy for Efficient Discovery of Cocrystals via a Network-Based Recommendation Model. Crystal Growth & Design, 20, 6820-6830.
https://doi.org/10.1021/acs.cgd.0c00911
|