Author(s):
Suzana, Kholis Amalia Nofianti, Melanny Ika Sulistyowaty, Juni Ekowati, Ade Novianto, Tutuk Budiati
Email(s):
suzana@ff.unair.ac.id
DOI:
10.52711/0974-360X.2025.00845 
Address:
Suzana1*, Kholis Amalia Nofianti1, Melanny Ika Sulistyowaty1, Juni Ekowati1, Ade Novianto2, Tutuk Budiati3
1Department of Pharmaceutical Science, Faculty of Pharmacy, Airlangga University, Surabaya 60115, Indonesia.
2Faculty of Pharmacy, Airlangga University, Surabaya 60115, Indonesia.
3Faculty of Pharmacy, Widya Mandala Chatholic University, Surabaya 60112, Indonesia.
*Corresponding Author
Published In:
Volume - 18,
Issue - 12,
Year - 2025
ABSTRACT:
The compound 2-ethylhexylcinnamate and its derivatives are known to have a protective effect on the skin against damage caused by UV radiation. A study was conducted to investigate the impact of hydroxyl groups in the para position on the synthesis of 2-ethylhexyl 4-hydroxycinnamate. In this study, compounds 2-ethylhexylcinnamate and 2-ethylhexyl 4-hydroxycinnamate were synthesized from cinnamic acid through nucleophilic acyl substitution reactions via the formation of acyl chloride compounds. The effect of hydroxyl groups in the para position was determined by comparing the percentage yield of 2-ethylhexyl 4-hydroxycinnamate to 2-ethylhexylcinnamate. The p-hydroxyl group is an electron-donating group that can influence the reactivity of the carbonyl group (C=O) through mesomery effects in the acylation reaction. The synthesis of 2-ethylhexyl 4-hydroxycinnamate (12.5%) resulted in a lower percentage yield compared to 2-ethylhexylcinnamate (55.8%). The result of the reaction was assessed for its purity using thin-layer chromatography. The identification of the synthesized product was performed through UV-Vis spectroscopy, infrared analysis, NMR and GC-MS. Hydroxyl groups in the para (p) position can reduce the reactivity of the carbon atom in the carbonyl group (C=O) in the acylation reaction of 2-ethylhexyl 4-hydroxycinnamate.
Cite this article:
Suzana, Kholis Amalia Nofianti, Melanny Ika Sulistyowaty, Juni Ekowati, Ade Novianto, Tutuk Budiati. The Influence of p-hydroxyl group on the Synthesis of 2-Ethylhexyl 4-Hydroxycinnamate. Research Journal Pharmacy and Technology. 2025;18(12):5855-0. doi: 10.52711/0974-360X.2025.00845
Cite(Electronic):
Suzana, Kholis Amalia Nofianti, Melanny Ika Sulistyowaty, Juni Ekowati, Ade Novianto, Tutuk Budiati. The Influence of p-hydroxyl group on the Synthesis of 2-Ethylhexyl 4-Hydroxycinnamate. Research Journal Pharmacy and Technology. 2025;18(12):5855-0. doi: 10.52711/0974-360X.2025.00845 Available on: https://rjptonline.org/AbstractView.aspx?PID=2025-18-12-35
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