Synthesis and Spectral Characterization of 4-Hydroxy-3- Methoxybenzaldehyde Derivatives

  • Mohd Razip Asaruddin
  • Sam Ezekiel
  • Mohammad Farhan Ariffeen
  • Md Abu Affan
Keywords: Vanillin, Schiff bases, Amines

Abstract

Vanillin plays an important role in flavouring and as aroma agent. Vanillin has been used as a chemical
intermediate in pharmaceutical and chemical syntheses. Schiff base products have been proved to poses
beneficial biological effect towards health. Fourteen vanillin derivatives were synthesized via Schiff base
reaction using p-vanillin as the starting material reacted with 2-aminobenzenethiol, furan-2-carbohydrazide, 2-
hydrazinylpyridine, 4-hydroxybenzohydrazide, acetohydrazide, benzohydrazide, (diphenylmethylidene)
hydrazine, pyridine-4-carbohydrazide, benzene-1,2-diamine, phenylhydrazine, 2-hydroxybenzohydrazide, 1,3-
benzothiazol-2-amine, 1-cyclohexylthiourea respectively. All of the compounds were characterized by elemental
analysis, FTIR and 1H NMR.

References

Armarego, W.L.F. & Perrin, D.D. (1996). Purification of laboratory chemicals. Fourth Edition. London, England: Elsevier Ltd.

Chobpattana, W., Jeon, I.J., & Smith, J.S. (2000). Kinetics of interaction of vanillin with amino acids and peptides in model systems. Journal of Agriculture and Food Chemistry, 48(9): 3885-3889.

https://doi.org/10.1021/jf9912102

Fitzgerald, D.J., Stratford, M., Gasson, M.J., & Narbad, A. (2005). Structure function analysis of the vanillin molecule and its antifungal properties. Journal of Agriculture and Food Chemistry, 53(5): 1769-1775.

https://doi.org/10.1021/jf048575t

Hodnett, E.M. & Dunn, W.J. (1970). Structure- antitumor activity correlation of some Schiff Bases. Journal of Medicinal Chemistry, 13(4): 768-770.

https://doi.org/10.1021/jm00298a054

Latif, N., Mishriky, N., & Assad, F.M. (1983). Carbonyl and thiocarbonyl compounds XX. Reaction of hydrobenzaldehydes with o-phenylenediamine; newer aspects in benzimidazole synthesis. Recueil Journal of the Royal Netherlands Chemical Society, 102(2): 73-77.

https://doi.org/10.1002/chin.198321215

Li, M.Y., Hu, P.Z., Zhu, W.R., & Xu, K.X. (2003). Synthesis of 2,6-(substituted) pyridine derivatives using amide and imine groups. Chinese Chemical Letters, 14(6): 572-574.

Litina, D.J.H. & Geronikaki, A.A. (1998). Thiazolyl and benzothiazolyl Schiff bases as novel possible lipogenase inhibitors and anti-inflammatory agents. Synthesis and Biological Evaluation. Drug Design and Discovery, 15(3): 199-206.

Pandeya S.N., Sriram, D., Nath, G., & Clereq, E.D. (1999a). Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine. IL Farmaco, 54(4): 624-628.

https://doi.org/10.1016/S0014-827X(99)00075-0

Pandeya S.N., Sriram, D., Nath, G., & Clereq, E.D. (1999b). Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derivatives from isatin derivatives and N-[4-(4'-chlorophenyl) thiazol-2-yl]thiosemicarbazide. European Journal of Pharmaceutical Sciences, 9(1): 25-31.

https://doi.org/10.1016/S0928-0987(99)00038-X

Pandeya S.N., Sriram, D., Nath, G., & Clereq, E.D. (1999c). Synthesis, antibacterial, antifungal and anti-HIV activities of Schiff and Mannich bases derivatives from isatin derivatives with 3-amino-2-methylmercaptoquinazolin-4-(3H)-one. Pharmaceutica Acta Helve, 74(1): 11-17.

https://doi.org/10.1016/S0031-6865(99)00010-2

Popp, F.D. (1964). Synthesis of potential antineoplastic agents X preparation and reactions of aldehydes related to benzaldehyde mustard. Journal of Medicinal Chemistry, 7(2): 210-212.

https://doi.org/10.1021/jm00332a018

Samadhiya, S. & Halve, A. (2001). A synthetic utility of Schiff bases as potential herbicidal agents. Orient Journal of Chemistry, 17(1): 119-122.

Walton, N.J., Mayer, M.J., & Narbad, A. (2003). Phytochemistry. Volume 63. Amsterdam: Elsevier Ltd. Pp 505-515.

https://doi.org/10.1016/S0031-9422(03)00149-3

How to Cite
Asaruddin, M. R., Ezekiel, S., Ariffeen, M. F., & Affan, M. A. (1). Synthesis and Spectral Characterization of 4-Hydroxy-3- Methoxybenzaldehyde Derivatives. Borneo Journal of Resource Science and Technology, 5(1), 43-48. https://doi.org/10.33736/bjrst.283.2015
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General