SYNTHESIS OF SOME CINNAMIC ACID DERIVATIVES: EFFECT OF GROUPS ATTACHED ON AROMATIC RING TO THE REACTIVITY OF BENZALDEHYDE

https://doi.org/10.22146/ijc.21626

Marcellino Rudyanto(1*), Lanny Hartanti(2)

(1) Research and Community Service Institute, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(2) Faculty of Pharmacy, Widya Mandala Catholic University, Jl. Dinoyo 42-44 Surabaya 60265
(*) Corresponding Author

Abstract


Synthesis of cinnamic acid and its six derivatives has been done by employing Knoevenagel reaction. Benzaldehyde, 4-butylbenzaldehyde, 4-t-butylbenzaldehyde, 4-butoxybenzaldehyde, 4-phenylbenzaldehyde, 5-bromo-2,4-dimethoxybenzaldehyde, and 5-bromo-2,3-dimethoxybenzaldehyde were reacted with malonic acid in pyridine – piperidine to give cinnamic acid (85,3%), 4-butylcinnamic acid (69,3%), 4-t-butylcinnamic acid (77,7%), 4-butoxycinnamic acid (64,5%), 4-phenylcinnamic acid (65,5%), 5-bromo-2,4-dimethoxycinnamic acid (53,2%) and 5-bromo-2,4-dimethoxycinnamic acid (57,2%), respectively. It was disclosed that 4-alkyl, 4-alkoxy, 4-aryl, dan 2-alkoxy groups decrease the reactivity of carbonyl carbon of benzaldehyde.


Keywords


cinnamic acid; cinnamic acid derivatives; Knoevenagel reaction

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References

[1] Duke, J. A., 2004. Dr. Duke’s Phytochemical and Ethnobotanical Databases, Http://www.ars-grin.gov/duke, diakses pada tanggal 12 Maret 2005.

[2] Tan, C., Zhu, W., and Lu, Y., 2002, Chin. Med. J., 115, 1859-1862

[3] Natella, F., Nardini, M., DiFelice, M., and Scaccini, C., 1999, J. Agric. Food. Chem., 47, 1453-1459.

[4] Yesilada, A., Zorlu, E., Aksu, F., and Yesilada, E., 1996, Farmaco, 51, 595-599.

[5] Sadono, 2001, Bioavailabilitas Etil p-metoksisinamat dari Perasan Rimpang Kencur pada Hewan Coba Kelinci, Tesis, Universitas Airlangga, Surabaya.

[6] Parfitt, K. (ed), 1999, Martindale The Complete Drug Reference, 32nd ed., Pharmaceutical Press, London.

[7] Knoerzer, T. A., 2003, Multi-step Synthesis of 3-Alkoxy-4-methoxy-6-nitro-trans-cinnamic acid. Http://www.naz.edu, diakses pada tanggal 18 Januari 2005.

[8] Avanti, C., 2002, Daya Hambat Epigalokatekin Galat (EGCG) dan Kombinasi Epigalokatekin Galat – Kojic Acid terhadap Aktivitas Tirosinase, Tesis, Universitas Airlangga, Surabaya.

[9] Sakuma, K., Ogawa, M., Sugibayashi, K., and Yamamoto, K., 1999, Acc. Pharm. Res., 22, 335-339.

[10] Kubo, I., Kinst-Hori, I., and Yokohama, Y., 1994, J. Nat. Prod., 57, 545-551.

[11] Glyglewski, R. J., 1974, Structure-Activity Relationship of Some Prostaglandin Synthetase Inhibitors. In: Robinson, H. J., and Vane, J. R. (eds), Prostaglandin Synthetase Inhibitors, Raven Press, New York.

[12] Shen, T. Y., 1981, Nonsteroidal Antiinflamatory Agent, In: Wolff, M. E. (ed), Burger’s Medicinal Chemistry, 4th ed., John Wiley and Sons, New York.

[13] McMurry, J., 2000, Organic Chemistry, 5th ed, Brooks/Cole, New York.

[14] Ekowati, J., 2003, Pengaruh Katalis pada Sintesis Asam o-Metoksisinamat dengan Material Awal o-Metoksibenzaldehida. Prosiding Seminar Nasional Himpunan Kimia Indonesia, 170-176.

[15] Wade, L. G., 1995, Organic Chemistry, 3th ed, Pretice-Hall, New Jersey.

[16] Isaacs, N, 1987. Physical Organic Chemistry, Essex, Longman Scientific & Technical.

[17] Sykes, P., 1989, Penuntun Mekanisme Reaksi Kimia Organik, edisi 6, terj. A.J. Hartomo dkk. Gramedia, Jakarta.



DOI: https://doi.org/10.22146/ijc.21626

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