A Novel Process for Synthesis of Cyclohexyl Ferulate


Article Preview

Cyclohexyl ferulate was prepared by direct sterification of ferulic acid and cyclohexanol as raw materials with sodium bisulfate supported by silica as a catalyst. The influences of some factors on the synthesis process were studied. The optimal reaction conditions based upon 0. 2 mol of ferulic acid were chosen that the molar ratio of cyclohexanol and ferulic acid was 10 : 1, the mass ratio of catalyst to reactants was 5%, refluing reaction time was 3.5 hours, et a1. The yield of the product reached 80%. The structure of the product was characterized by IR, 1H NMR and MS spectrum. The catalyst could be recycled and used for many times, which is friendly to the environment.



Advanced Materials Research (Volumes 781-784)

Edited by:

Lin Yu, Jianwei Guo, Guobin Yi and Qian Yu




X. W. Kong et al., "A Novel Process for Synthesis of Cyclohexyl Ferulate", Advanced Materials Research, Vols. 781-784, pp. 283-286, 2013

Online since:

September 2013




* - Corresponding Author

[1] Fashe Li, Guirong Bao, Hua Wang. Research advance in oxidative stability of biodiesel [J]. China Oils and Fats [J]. 2009, 34(2): 1-5. In Chinese.

[2] Cione E, Tucci P, Senatore V, et al. Synthesized esters of ferulic acid induce release of cytochrome c from rat testes mitochondria [J]. Journal of Bioenergetics and Biomembranes, 2008, 40(1): 19-26.

DOI: https://doi.org/10.1007/s10863-007-9097-7

[3] Fang X, Kikuchi S, Shima M, et al. Suppressive effect of alkyl ferulate on the oxidation of microencapsulated linoleic acid [J]. European Journal of Lipid Science and Technology [J]. 2006, 108(2): 97-102.

DOI: https://doi.org/10.1002/ejlt.200500258

[4] Fang X, Shima M, Kadota M, et al. Suppressive effect of alkyl ferulate on the oxidation of linoleic acid. Bioscience, Biotechnology, and Biochemistry [J]. 2006, 70(2): 457-461.

DOI: https://doi.org/10.1271/bbb.70.457

[5] Chikuno T, Kato H, Kadota M. Skin-lightening cosmetics containing ferulic acid esters [P]. JP2005350425, 2005-12-22.

[6] Taniguchi H, Nomura E, Hosoda A, et al. Ferulic acid or derivative thereof as inhibitor and regulator of germination[P]. JP2003040709, 2003-02-13.

[7] Kikuzaki H, Hisamoto M, Hirose K, et al. Antioxidant Properties of Ferulic Acid and Its Related Compounds[J]. Journal of Agricultural and Food Chemistry, 2002, 50(7): 2161-2168.

DOI: https://doi.org/10.1021/jf011348w

[8] Murakami A, Kadota M, Takahashi D, et al. Suppressive effects of novel ferulic acid derivatives on cellular responses induced by phorbol ester, and by combined lipopolysaccharide and interferon[J]. Cancer Letters (Shannon, Ireland), 2000, 157(1): 77-85.

DOI: https://doi.org/10.1016/s0304-3835(00)00478-x

[9] Zhihua Song, Bo Gao, Xingguo Wang, et al. Enzymatic synthesis of feruloylated structolipids in two steps with a solvent-free system [P]. China Oils and Fats, 2009, 34(12): 45-47. In Chinese.

[10] Qingfang Cheng, Qifa Wang, Xingyou Xu, et al. Synthesis of 3-Cinnamoylisoferulic Acid Phenyl Esters under Ultrasonic Irradiation [P]. Chinese Journal of Pharmaceuticals, 2010, 41(2): 88-90. In Chinese.

[11] Jianhong Tang, Qingyou Zeng. One-pot Synthesis of 2-Ethylhexyl-3-(4-hydroxy-3-meth ox yphenyl) acrylate [P]. Fine Chemicals, 2010, 27(8): 793-795. In Chinese.

[12] Yoshida Y, Kimura Y, Kadota M, et al. Continuous synthesis of alkyl ferulate by immobilized Candida antarctica lipase at high temperature [P]. Biotechnology Letters, 2006, 28(18): 1471-1474.

DOI: https://doi.org/10.1007/s10529-006-9113-8

[13] Giuliani S, Piana C, Setti L, et al. Synthesis of pentylferulate by a feruloyl esterase from Aspergillus niger using water-in-oil microemulsions[P]. Biotechnology Letters, 2001, 23(4): 325-330.

[14] Cassani J, Luna H, Navarro A, et al. Comparative esterification of phenylpropanoids versus hydrophenylpropanoids acids catalyzed by lipase in organic solvent media [P]. Electronic Journal of Biotechnology, 2007, 10(4): 508-513.

DOI: https://doi.org/10.2225/vol10-issue4-fulltext-3

[15] Jayaprakasam B, Vanisree M, Zhang Y J, et al. Impact of Alkyl Esters of Caffeic and Ferulic Acids on Tumor Cell Proliferation, Cyclooxygenase Enzyme, and Lipid Peroxidation[P]. Journal of Agricultural and Food Chemistry, 2006, 54(15): 5375-5381.

DOI: https://doi.org/10.1021/jf060899p

[16] Jiaying Xin, Yan Zhang, Guanli Zhao, et al. Application and Synthesis of Ferulic Acid and Its Derivatives [P]. Chemical World, 2006, (5): 305-307. In Chinese.

[17] Li N G, Shi Z H, Tang Yu P, et al. Highly efficient esterification of ferulic acid under microwave irradiation [P]. Molecules, 2009, 14(6): 2118-2126.

DOI: https://doi.org/10.3390/molecules14062118

[18] Shengzhao Gong, Jia Li, Zhimian Yun, et al. Synthesis of amyl ferulate catalyzed by sodium hydrogen sulfate [P]. Chemical Research and Application, 2012, 24(1): 94-96. In Chinese.

[19] Baoquan Li, Nianguang Li, Feng Feng, et al. Synthesis and anti-platelet aggregation activities of ferulic acid esters [P]. Journal of China Pharmaceutical University, 2009, (6): 486-490. In Chinese.

[20] Fanlong Meng, Qingyi Zhang, Shuo Li, et al. Study on Synthesis and Antibacterial Activity of Cyclohexyl Ferulate [J]. Chemical World, 2012, 53(1): 45-47. In Chinese.

[21] Xiangwen Kong, Long Yu. Synthesis of n-butyl acetate catalyzed by solid superacid SO42-/Fe2O3 [J]. Experimental Technology and Management, 2011, 28(5): 30-31, 40. In Chinese.

Fetching data from Crossref.
This may take some time to load.