Structural analysis of products arising from the interaction between L-ascorbic acid and p-aminoacetanilide
https://doi.org/10.21285/achb.1014
EDN: RUQCNS
Abstract
Products of reactions between L-ascorbic acid and various nitrogen-containing biologically active substances can be used to develop new preparations with promising applications in the pharmaceutical, food, and cosmetic industries. The present study examined the interaction of L-ascorbic acid with p-aminoacetanilide in ethanol medium at component ratios of 1:1 and 1:2. The target products were obtained by controlling the temperature of aqueous ethanol solutions containing the specified amounts of components (50 °С, 1 h), which was followed by slow solvent removal for 24 h. Immediately after the temperature control stage, the reaction systems, in the form of thin films on KBr substrates, were analyzed via vibrational spectroscopy. Following slow solvent removal, the solid phases washed with anhydrous ether and its mixture with ethanol were studied in a KBr matrix using infrared spectroscopy. The vibrational spectra of the 1:1 reaction system revealed that no ionic associate is formed during the temperature control stage; subsequent solvent removal leads to the release of the solid phase of co-crystallization product, whose formation is confirmed by analysis of the mid- and near-infrared spectra. With the 1:2 component ratio, the reaction system was found to form a Schiff base at the C 3 of ascorbic acid during the temperature control stage, which subsequently rearranged during slow solvent removal into a 3-substituted N-derivative of ascorbic acid (3-deoxy-3-(p-acetamidophenylamino)-L-ascorbic acid). The electronic spectra of both reaction systems indicate insignificant side processes of melanoidin formation under the selected experimental conditions. According to published sources, the structural analogs of released products are characterized by sufficient stability compared to aliphatic derivatives, as well as notable antioxidant properties, which indicates the importance of their further study.
About the Authors
I. S. Cherepanov
Udmurt State University
Russian Federation
Russian Federation
Igor S. Cherepanov, Cand. Sci. (Chemistry), Associate Professor
1, Universitetskaya St., Izhevsk, 426034
D. A. Tarasova
Udmurt State University
Russian Federation
Russian Federation
Dar’ya A. Tarasova, Assistant
1, Universitetskaya St., Izhevsk, 426034
A. I. Egorova
Udmurt State University
Russian Federation
Russian Federation
Alina I. Egorova, Assistant
1, Universitetskaya St., Izhevsk, 426034
References
1. Spizzirri U., Garullo G., De Cicco L., Crispini A., Scarpelli F., Restuccia D., et al. Synthesis and characterization of a (+)-catechin and L(+)-ascorbic acid cocrystal as a new functional ingredient for tea drink. Heliyon. 2019;5(8):e02291. DOI: 10.1016/j.heliyon.2019.e02291.
2. Levy R., Okun Z., Shpigelman A. The influence of chemical structure and the presents of ascorbic acid on anthocyanins stability and spectral properties in purified model systems. Foods. 2019;8(6):207. DOI: 10.3390/foods8060207.
3. Inoue Y., Horage M., Suzuki R., Niiyama D., Urano R., Ando S., et al. Study on complexation of ascorbic acid derivatives with γ-cyclodextrin. International Journal of Pharmacy. 2017;7(1):9-21.
4. Chanphai P., Tajmir-Riahi H. Conjugation of vitamin C with serum proteins: a potential application for vitamin delivery. International Journal of Biological Macromolecules. 2019;137:966-972. DOI: 10.1016/j.ijbiomac.2019.07.059.
5. Palanisamy V., Sanphui P., Palanisamy K., Prakash M., Bansail A.K. Design of ascorbic acid eutectic mixtures with sugars to inhibit oxidative degradation. Frontiers in Chemistry. 2022;10:754269. DOI: 10.3389/fchem.2022.754269.
6. Zhang H., Zeng H., Li M., Song Y., Tian S., Xiong J., et al. Novel ascorbic acid co-crystal formulations for improved stability. Molecules. 2022;27(22):7998. DOI: 10.3390/molecules27227998.
7. Farias M.D.P., Albuquerque P.B.S., Soares P.A.G., de Sá D.M.A.T., Vicente A.A., Carneiro-da-Cunha M.G. Xyloglucan from Hymenaea courbaril var. courbaril seeds as encapsulating agent of L-ascorbic acid. International Journal of Biological Macromolecules. 2018;107:1559-1566. DOI: 10.1016/j.ijbiomac.2017.10.016.
8. Garnero C., Longhi M. Study of ascorbic acid interaction with hydroxypropyl-β-cyclodextrin and triethanolamine, separately and in combination. Journal of Pharmaceutical and Biomedical Analysis. 2007;45(4):536-545. DOI: 10.1016/j.jpba.2007.07.030.
9. Xavier A.J.M., Raj M.A., Marie J.M. Synthesis and spectral characterization of an aminoacetophenone-based Schiff base and its interaction studies with ascorbic acid. Journal of Chemical and Pharmaceutical Research. 2012;4(1):669-672.
10. Sarybayeva B.D, Pishchugin F.V, Tuleberdiev I.T. Kinetics and the mechanism of interaction of L-ascorbic acid with nitrogen-containing organic compounds. Nauchnoe obozrenie. Mezhdunarodnyi nauchno-prakticheskii zhurnal. 2017;3:66. (In Russian). EDN: ZGIVYP.
11. Pischetsrieder M., Larisch B., Muller U., Severin T. Reaction of ascorbic acid with aliphatic amines. Journal of Agricultural and Food Chemistry. 1995;43(12):3004-3006. DOI: 10.1021/jf00060a002.
12. Dikusar E.A., Kozlov N.G., Mel’nichuk L.A. Salts of L-ascorbic acid with certain substituted amines and triphenylphosphine. Chemistry of Natural Compounds. 2004;40:406-407. DOI: 10.1023/B:CONC.0000048259.21776.2e.
13. Malinkina O.N., Provozina A.A., Shipovskaya A.B. Evaluation of the chemical interaction between chitosan hydrochloride and ascorbic acid by IR and NMR spectroscopy. Izvestiya of Saratov University. Chemistry. Biology. Ecology. 2014;14(3):20-24. (In Russian). EDN: SXUADF.
14. Cherepanov I.S. Synthesis and antioxidative activity of D-glucose - p-aminoacetanilide condensation products. Chemistry and Technology of Organic Substances. 2020;3:71-78. (In Russian). DOI: 10.54468/25876724_2020_3_71. EDN: ZFCPUG.
15. Abraham J.P., Sajan D., Hubert Joe I., Jayakumar J.S. Molecular structure, spectroscopic studies and first-order molecular hyperpolarizabilities of p-aminoacetanilide. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy. 2008;71(2):355-367. DOI: 10.1016/j.saa.2008.01.010.
16. Cherepanov I.S., Korepanova Ya.S. Behavior of N-glycosylaryldiamine antioxidants under oxidative stress conditions. Technology and merchandising of the innovative foodstuff. 2021;1:3-7. (In Russian). DOI: 10.33979/2219-8466-2021-66-1-3-7. EDN: VIONRL.
17. Pirniyazov K.K., Anvarova G.K., Rashidova S.Sh. Effect of synthesis conditions on the complexation of chitosan with ascorbic acid. Proceedings of the RAS Ufa Scientific Centre. 2018;3:72-74. (In Russian). EDN: XWQPKH.
18. Casian T., Reznek A., Vonica-Gligor A.L., Van Renterghem J., De Beer T., Tomuță I. Development, validation and comparison of near infrared and Raman spectroscopic methods for fast characterization of tablets with amlodipine and valsartan. Talanta. 2017;167:333-343. DOI: 10.1016/j.talanta.2017.01.092.
19. Dabbagh H.A., Azami F., Farrokhpour H., Chermahini N. UV-Vis, NMR and FTIR spectra of tautomers of vitamin C. Experimental and DFT calculation. Journal of the Chilean Chemical Society. 2014;59(3):2248-2254. DOI: 10.4067/S0717-97072014000300013.
20. Ferrer E., Williams P., Baran E. Interaction of vanadyl (IV) cation with L-ascorbic acid and related system. Zeitschrift für Naturforschung B. 1998;53(2):256-262. DOI: 10.1515/znb-1998-0220.
21. Lohmann W., Pagel D., Penka V. Structure of ascorbic acid and its biological activity. Determination of the conformation of ascorbic acid and isoascorbic acid by infrared and ultraviolet investigation. European Journal of Biochemistry. 1984;138(3):479-480. DOI: 10.1111/j.1432-1033.1984.tb07941.x.
22. Saleh T.A.-K., Al-Samarrai R.R.H., Abdul-Razzaq N.E. The antioxidant and antimicrobial activity for some new synthesized Schiff base derived from ascorbic acid. International Journal of Research in Pharmaceutical Sciences. 2019;10(2):1510-1515. DOI: 10.26452/ijrps.v10i2.730.
23. Tajmir-Riahi H.A. Coordination chemistry of vitamin C. Part I. Interaction of L-ascorbic acid with alkaline earth metal ions in the crystalline solid and aqueous solution. Journal of Inorganic Biochemistry. 1990;40(2):181-188. DOI: 10.1016/0162-0134(90)80051-x.
24. Onoda H., Inoue Y., Ezawa T., Murata I., Chantadee T., Limmatvapirat S., et al. Preparation and characterization of triamterene complex with ascorbic acid derivatives. Drug Development and Industrial Pharmacy. 2020;46(12):2032-2040. DOI: 10.1080/03639045.2020.1842439.
25. Wang L., Choi W.M., Chung J.S., Hur S.H. Multicolor emitting N-doped carbon dotes derived from ascorbic acid and phenylenediamine precursors. Nanoscale Research Letters. 2020;15:222. DOI: 10.1186/s11671-020-03453-3.
26. Wang P., Wang Y., Sun Y., Cao Z., Zhu W., Wang H. Thermal and spectroscopic studies of the thermal-oxidation stabilities of lubricants. Journal of Applied Spectroscopy. 2021;88:847-854. DOI: 10.1007/s10812-021-01249-6.
Review
For citations:
Cherepanov I.S., Tarasova D.A., Egorova A.I. Structural analysis of products arising from the interaction between L-ascorbic acid and p-aminoacetanilide. Proceedings of Universities. Applied Chemistry and Biotechnology. 2025;15(4):446-455. (In Russ.) https://doi.org/10.21285/achb.1014. EDN: RUQCNS
Views:
69
Email this article 