Synthesis of PMCA (P-Methoxy Cinnamic Acid) using Perkin Reaction and Its Activity as Photo Protective and Antifungal Agent

Yuliana Purwaningsih, Erwin Indriyanti, Ahmad Fuad Masduqi


This study aimed to synthesize p-methoxy cinnamic acid through the Perkin reaction and to determine its activity as a photoprotective and antifungal agent against Candida albicans. The PMCA compound was synthesized by reacting p-methoxy benzaldehyde with acetic anhydride using a sodium acetate catalyst in a sonicator at 50oC for 60 minutes. The synthesized was a white precipitate with a % yield of 2.09% and a melting point of 172-175oC. ATR-FTIR identified this compound with several functional groups, C=O, OH carboxylic acid, para-substituted benzene, and C=C. Analysis by GC-MS showed a single peak at a retention time of 11.710 minutes with m/z 178. Characterization of this compound by 1H-NMR spectrometry showed several chemical shifts showing the presence of OH groups of carboxylic acids, C=C groups, aromatic benzene groups, and methoxy. The results of this characterization indicated that the synthesis product was PMCA. The antioxidant activity of PMCA using the DPPH radical gave IC50 at a concentration of 352.6138 ppm. In vitro sunscreen activity against PMCA compounds provided high protection at a concentration of 30 ppm with SPF 32,505. The antifungal activity against Candida albicans showed inhibition zones of 0.257cm± 0.044, 1.397cm± 0.093, and 1.533cm± 0.111, respectively at concentrations of 5%, 10%, and 15%. The PMCA compounds can be synthesized through the Perkin reaction assisted by ultrasonic waves and can potentially be photoprotective and antifungal agents.


antifungal; antioxidant; p-methoxy cinnamic acid; photoprotective; sunscreen

Full Text:



[1] A. Płowuszyńska and A. Gliszczyńska, “Recent developments in therapeutic and nutraceutical applications of p-methoxycinnamic acid from plant origin,” Molecules, vol. 26, no. 13, pp. 1–17, 2021,

doi: 10.3390/molecules26133827.

[2] M. S. Fareza, “Transformation Of Ethyl-P-Methoxycinnamate To P – Methoxycinnamic Acid From Kencur (Kaempheria Galanga L.) And Their Antibacterial Activity,” ALCHEMY J. Penelit. Kim., vol. 13, no. 2, pp. 176–190, 2017,

doi: 10.20961/alchemy.v13i2.8472.

[3] A. F. Masduqi, E. Indriyanti, and R. S. Dinurrosifa, “Antibacterial Activity Testing on APMS (p-Methoxy Cinnamic Acid) Against Escherichia coli Bacteria,” J. Ilm. Sains, vol. 21, no. 2, p. 155, 2021,

doi: 10.35799/jis.v21i2.35684.

[4] S. Gunasekaran, K. Venkatachalam, and N. Namasivayam, “Anti-inflammatory and anticancer effects of p-methoxycinnamic acid, an active phenylpropanoid, against 1,2-dimethylhydrazine-induced rat colon carcinogenesis,” Mol. Cell. Biochem., vol. 451, no. 1–2, pp. 117–129, 2019, doi: 10.1007/s11010-018-3398-5.

[5] S. Adisakwattana, “Cinnamic acid and its derivatives: Mechanisms for prevention and management of diabetes and its complications,” Nutrients, vol. 9, no. 2, 2017,

doi: 10.3390/nu9020163.

[6] N. Kumar and A. Parle, “Cinnamic acid derivatives : An ERA,” Pharma Innov. J., vol. 8, no. 5, pp. 580–595, 2019.

Google Scholar

[7] M. Edwards, P. M. Rourk, P. G. Riby, and A. P. Mendham, “Not quite the last word on the Perkin reaction,” Tetrahedron, vol. 70, no. 40, pp. 7245–7252, 2014,

doi: 10.1016/j.tet.2014.07.053.

[8] H. A. D. Chen, ‎ S.K. Sharma, A. Mudhoo (Eds.), Handbook on Applications of Ultrasound, Sonochemistry for Sustainability. Boca Raton: CRC Press, 2012.

ISBN: 9781439842065.

[9] Y. Purwaningsih, M. Syukur, U. Rizki, and E. Purwanto, “Sonochemical Synthesis Of Ethyl Cinnamate,” JKPK (JURNAL Kim. DAN Pendidik. Kim., vol. 5, no. 1, pp. 1–7, 2020,

doi: 10.20961/jkpk.v5i1.35525.

[10] E. Indriyanti and M. S. Prahasiwi, “Synthesis of Cinnamic Acid based on Perkin Reaction using Sonochemical Method and Its Potential as Photoprotective Agent,” JKPK(Jurnal Kim. dan Pendidik. Kim., vol. 5, no. 1, pp. 54–61, 2020, doi: 10.20961/jkpk.v5i1.38136.

[11] A. Anggadita, Ngadiwiyanaa, and Ismiyarto, “Sintesis Amil Sinamat dari Sinamaldehid dan Uji Aktivitas sebagai Bahan Aktif Tabir Surya,” J. Kim. Sains dan Apl., vol. 11, no. 3, pp. 52–56, 2008,

doi: 10.14710/jksa.15.2.39-43.

[12] T. Buxton, S. Takahashi, A. M. Eddy Doh, J. Baffoe-Ansah, E. O. Owusu, and C. S. Kim, “Insecticidal activities of cinnamic acid esters isolated from Ocimum gratissimum L. and Vitellaria paradoxa Gaertn leaves against Tribolium castaneum Hebst (Coleoptera: Tenebrionidae),” Pest Manag. Sci., vol. 76, no. 1, pp. 257–267, 2020,

doi: 10.1002/ps.5509.

[13] M. A. Khan, “Sun Protection Factor Determination Studies of Some Sunscreen Formulations Used in Cosmetics for Their Selection,” J. Drug Deliv. Ther., vol. 8, no. 5-s, pp. 149–151, 2018,

doi: 10.22270/jddt.v8i5-s.1924.

[14] A. F. Masduqi and M. Syukur, “Antifungal Activity Test of Pletekan Leaves Liquid Soap (Ruellia tuberosa L.) on Candida albicans,” JFSP, vol. 7, no. 2, pp. 180–188, 2021,

doi: 10.31603/pharmacy.v7i2.4563.

[15] M. Draye, G. Chatel, and R. Duwald, “Ultrasound for drug synthesis: A green approach,” Pharmaceuticals, vol. 13, no. 2, 2020,

doi: 10.3390/ph13020023.

[16] G. Rabbani, “A Concise Introduction of Perkin Reaction,” Org. Chem. Curr. Res., vol. 07, no. 02, pp. 7–10, 2018,

doi: 10.4172/2161-0401.1000191.

[17] E. Veverková, E. Pacherová, and Š. Toma, “Examination of the Perkin reaction under microwave irradiation,” Chem. Pap., vol. 53, no. 4, pp. 257–259, 1999.

Google Scholar

[18] S. Deo, T. Chaudhari, and F. Inam, “Microwave assisted Perkin reaction for the synthesis of α-arylidine-γ-phenyl-Δ, β, γ-butenolides,” Indian J. Chem. - Sect. B Org. Med. Chem., vol. 53, no. 3, pp. 363–367, 2014, doi: 10.1002/chin.201437116.

[19] E. Indriyanti, M. S. P, Y. Purwaningsih, and F. X. Sulistiyanto, “Temperature Optimization Against P-Methoxycinamic Acid Synthesis Through Ultrasonic Wave-Assisted Knoevenagel Condensation,” J. Chem., vol. 16, no. 1, pp. 101–108, 2022,

doi: 10.24843/JCHEM.2022.v16.i01.p13.

[20] S. Mumtazuddin and S. K. Sinhai, “Perkin reactions under microwave irradiation,” Asian J. Chem., vol. 19, no. 6, pp. 4945–4947, 2007.

Google Scholar

[21] H. Nurhasnawati, R. Sundu, Sapri, R. Supriningrum, H. Kuspradini, and E. T. Arung, “Antioxidant activity, total phenolic and flavonoid content of several indigenous species of ferns in East Kalimantan, Indonesia,” Biodiversitas, vol. 20, no. 2, pp. 576–580, 2019,

doi: 10.13057/BIODIV/D200238.

[22] P. Sharma, “Cinnamic acid derivatives: A new chapter of various pharmacological activities,” J. Chem. Pharm. Res., vol. 3, no. 2, pp. 403–423, 2011.

Google Scholar

[23] A. Gunia-Krzyżak, K. Słoczyńska, J. Popiół, P. Koczurkiewicz, H. Marona, and E. Pękala, “Cinnamic acid derivatives in cosmetics: current use and future prospects,” Int. J. Cosmet. Sci., vol. 40, no. 4, pp. 356–366, 2018,

doi: 10.1111/ics.12471.

[24] K. Geoffrey, A. N. Mwangi, and S. M. Maru, “Sunscreen products: Rationale for use, formulation development and regulatory considerations,” Saudi Pharm. J., vol. 27, no. 7, pp. 1009–1018, 2019, doi: 10.1016/j.jsps.2019.08.003.

[25] M. S. Latha et al., “Sunscreening agents: A review,” J. Clin. Aesthet. Dermatol., vol. 6, no. 1, pp. 16–26, 2013.

Google Scholar

[26] L. Thi, N. Ngoc, V. Van Tran, J. Moon, M. Chae, and D. Park, “Recent Trends of Sunscreen Cosmetic :,” Cosmetics, no. Figure 1, pp. 1–15, 2019,

doi: 10.3390/cosmetics6040064.

[27] J. D. Guzman, “Natural cinnamic acids, synthetic derivatives and hybrids with antimicrobial activity,” Molecules, vol. 19, no. 12, pp. 19292–19349, 2014,

doi: 10.3390/molecules191219292.


  • There are currently no refbacks.