Microwave-Assisted Method for Synthesizing UV-Protective Methoxy-Benzylidene Cyclohexanone Derivatives Using Green Solvents

Muchammad Ikmal Abdillah; Dayu Arinda; Dini  Rohmawati; Cornelia  Budimarwanti; Sri Handayani

doi:10.15408/jkv.v12i1.46773

Authors

Muchammad Ikmal Abdillah Department of Chemistry Education, Faculty of Mathematics and Natural Sciences, Universitas Negeri Yogyakarta https://orcid.org/0009-0005-5543-8207
Dayu Arinda Department of Chemistry Education, Faculty of Mathematics and Natural Sciences, Universitas Negeri Yogyakarta https://orcid.org/0009-0008-2896-561X
Dini Rohmawati Department of Chemistry Education, Faculty of Mathematics and Natural Sciences, Universitas Negeri Yogyakarta https://orcid.org/0009-0001-9877-8026
Cornelia Budimarwanti Department of Chemistry Education, Faculty of Mathematics and Natural Sciences, Universitas Negeri Yogyakarta https://orcid.org/0009-0002-1795-4225
Sri Handayani Department of Chemistry Education, Faculty of Mathematics and Natural Sciences, Universitas Negeri Yogyakarta https://orcid.org/0000-0001-5771-4432

DOI:

https://doi.org/10.15408/jkv.v12i1.46773

Keywords:

Benzylidene cyclohexanone, green synthesis, microwave-assisted, solvent, sun protection factor

Abstract

Benzylidene cyclohexanone derivatives are known for their significant biological activities; however, traditional synthesis methods often involve non-eco-friendly processes and solvents. This research aims to identify the optimal solvent for maximum yield and to evaluate the UV-protection activity. The synthesis was conducted through a Claisen-Schmidt condensation reaction under NaOH catalysis with microwave irradiation for 60 seconds. Solvents tested included H₂O, H₂O/MeOH (1:1 v/v), H₂O/EtOH (1:1 v/v), MeOH, and EtOH. Reaction purity was assessed using TLC scanning. The product with the highest purity was recrystallized from EtOH and characterized by melting point, UV-Vis, FT-IR, ¹H-NMR, and GC-MS analysis. The UV-protection activity was evaluated in vitro. The results indicate the successful synthesis of two benzylidene cyclohexanone derivatives: (2E,6E)-bis(4-methoxybenzylidene) cyclohexanone (yellow needles) and (E)-2-(4-methoxybenzylidene) cyclohexanone (orange). The H₂O/MeOH (1:1 v/v) solvent provided the highest yields of 58.49% and 62.71%, respectively. The (2E,6E)-bis(4-methoxybenzylidene) cyclohexanone demonstrated a high SPF value of 9.908, offering maximum protection at 50 ppm concentration, while the mixed compound, (E)-2-(4-methoxybenzylidene) cyclohexanone, achieved an SPF of 15.324, categorized as ultra protection.

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