European Journal of Chemistry 2015, 6(4), 367-373 | doi: https://doi.org/10.5155/eurjchem.6.4.367-373.1298 | Get rights and content






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New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids


La Ode Kadidae (1) , Akira Usami (2) , Tomoya Koyama (3) , Mitsunori Honda (4,*) , Ko-Ki Kunimoto (5)

(1) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
(2) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
(3) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
(4) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
(5) Division of Material Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-Machi, Kanazawa, 920-1192, Japan
(*) Corresponding Author

Received: 10 Jul 2015 | Revised: 04 Aug 2015 | Accepted: 08 Aug 2015 | Published: 31 Dec 2015 | Issue Date: December 2015

Abstract


Caffeoylquinic acids (CQAs) are a group of the phenylpropanoids produced by certain plant species, which have various biological activities including antioxidant, antibacterial, anticancer, and others. Several synthetic routes have been developed using quinic acids (QAs) and caffeic acid derivatives as starting materials. In this study, alternative pathways of 3- and 5-CQAs preparation using protected quinic acids are described. Both CQAs were achieved by removal of the protecting groups of compound 9 and 18 with acid hydrolysis using dilute HCl solution. These compounds (9 and 18) are novel, resulted from esterification reaction of diacetyl caffeoyl chloride and protected quinic acids. The hydroxyl groups of quinic acid in this case were protected with 2,2-dimethoxy propane or tert-butyldimethylsilyl (TBS) chloride.


Keywords


Hydrolysis; Esterification; Chemical synthesis; Caffeoylquinic acids; Protected quinic acids; Dimethoxy caffeoyl chloride

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DOI: 10.5155/eurjchem.6.4.367-373.1298

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Funding information


Kanazawa University SAKIGAKE Project and Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number 15K05585.

Citations

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[1]. Wenwu Liu, Jingda Li, Xuemei Zhang, Yuxin Zu, Yue Yang, Wenjie Liu, Zihua Xu, Huan Gao, Xue Sun, Xiaowen Jiang, Qingchun Zhao
Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis
Journal of Agricultural and Food Chemistry  , , 2020
DOI: 10.1021/acs.jafc.0c03804
/


References

[1]. Clifford, M. N. J. Sci. Food Agr. 1999, 79, 362-372.
http://dx.doi.org/10.1002/(SICI)1097-0010(19990301)79:3<362::AID-JSFA256>3.0.CO;2-D

[2]. Jaiswal, R.; Matei, M. F.; Golon, A.; Wittb, M.; Kuhnert, N. Food Funct. 2012, 3, 976-984.
http://dx.doi.org/10.1039/c2fo10260a

[3]. Upadhyay, R.; Rao, L. J. M. Crit. Rev. Food Sci. 2013, 53, 968-984.
http://dx.doi.org/10.1080/10408398.2011.576319

[4]. De Maria, C. A. B.; Trugo, L. C.; De Mariz e Miranda, L. S. J. Food Compos. Anal. 1999, 12 (4), 289–292.
http://dx.doi.org/10.1006/jfca.1999.0833

[5]. El-Rehem, F. A.; El-Rehem, A. A.; Ali, R. F. M. Eur. J. Chem. 2013, 4(3), 185-190.
http://dx.doi.org/10.5155/eurjchem.4.3.185-190.711

[6]. Fujioka, K.; Shibamoto, T. J. Agr. Food Chem. 2006, 54, 6054-6058.
http://dx.doi.org/10.1021/jf060460x

[7]. Miyamae, Y.; Kurisu, M.; Murakami, K.; Han, J.; Isoda, H.; Irie, K.; Shigemori, H. Bioorgan. Med. Chem. 2012, 20, 5844–5849.
http://dx.doi.org/10.1016/j.bmc.2012.08.001

[8]. Kamiyama, M.; Moon, J-K.; Jang, H. W.; Shibamoto, T. J. Agr. Food Chem. 2015, 63, 1996-2005.
http://dx.doi.org/10.1021/jf5060563

[9]. Hemmerle, H.; Burger, H-J.; Below, P.; Schubert, G.; Rippel, R.; Schindler, P. W.; Paulus, E.; Herling, A. W. J. Med. Chem. 1997, 40 (2), 137-145.
http://dx.doi.org/10.1021/jm9607360

[10]. Lorentz, C.; Dulac, A.; Pencreac'h, G.; Ergan, F.; Richomme, P.; Soultani-Vigneron, S. Biotechnol. Lett. 2010, 32, 1955-1960.
http://dx.doi.org/10.1007/s10529-010-0386-6

[11]. Sefkow, M.; Kelling, A.; Schilde, U. Eur. J. Org. Chem. 2001, 14, 2735-2742
http://dx.doi.org/10.1002/1099-0690(200107)2001:14<2735::AID-EJOC2735>3.0.CO;2-I

[12]. Sefkow, M. Eur. J. Org. Chem. 2001, 6, 1137-1141.
http://dx.doi.org/10.1002/1099-0690(200103)2001:6<1137::AID-EJOC1137>3.0.CO;2-2

[13]. Dokli, I.; Navarini, L.; Hamersak, Z. Tetrahedron: Asym. 2001, 24 (13-14), 785-790.
http://dx.doi.org/10.1016/j.tetasy.2013.06.002

[14]. Sanchez-Abella, L.; Fernandez, S.; Armesto, N.; Ferrero, M.; Gotor, V. J. Org. Chem. 2006, 71 (14), 5396-5399.
http://dx.doi.org/10.1021/jo0606249

[15]. Manthey, M. K.; Gonzalez-Bello, C.; Abell, C. J. Chem. Soc., Perk. T. 1. 1997, 5, 625-628.

[16]. Maring, C. J.; Giranda, V. L.; Gu, Y. G.; Hanessian, S.; Kempf, D. J.; Madigan, D. L.; Stewart, K.; Stoll, V. S.; Sun, M.; Wang, G. T.; Wang, J.; Zhao, C. United States Patent No. US 6,593,314 B1, July 15, 2003.

How to cite


Kadidae, L.; Usami, A.; Koyama, T.; Honda, M.; Kunimoto, K. Eur. J. Chem. 2015, 6(4), 367-373. doi:10.5155/eurjchem.6.4.367-373.1298
Kadidae, L.; Usami, A.; Koyama, T.; Honda, M.; Kunimoto, K. New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids. Eur. J. Chem. 2015, 6(4), 367-373. doi:10.5155/eurjchem.6.4.367-373.1298
Kadidae, L., Usami, A., Koyama, T., Honda, M., & Kunimoto, K. (2015). New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids. European Journal of Chemistry, 6(4), 367-373. doi:10.5155/eurjchem.6.4.367-373.1298
Kadidae, La, Akira Usami, Tomoya Koyama, Mitsunori Honda, & Ko-Ki Kunimoto. "New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids." European Journal of Chemistry [Online], 6.4 (2015): 367-373. Web. 26 Sep. 2020
Kadidae, La, Usami, Akira, Koyama, Tomoya, Honda, Mitsunori, AND Kunimoto, Ko-Ki. "New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids" European Journal of Chemistry [Online], Volume 6 Number 4 (31 December 2015)

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DOI Link: https://doi.org/10.5155/eurjchem.6.4.367-373.1298

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