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






  OPEN ACCESS | PEER-REVIEWED | RESEARCH ARTICLE | DOWNLOAD PDF | VIEW FULL-TEXT PDF | TOTAL VIEWS

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

Full Text:

PDF /    /


DOI: 10.5155/eurjchem.6.4.367-373.1298

Links for Article


| | | | |

| | | | | | |

Related Articles




Article Metrics

This Abstract was viewed 914 times | PDF Article downloaded 375 times

Funding information


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

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. 27 Jan. 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)

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

| | | | |

| | | | | |

Save to Zotero Save to Mendeley

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

Refbacks

  • There are currently no refbacks.




Copyright (c)




© Copyright 2019  Atlanta Publishing House LLC All Right Reserved.

The opinions expressed in all articles published in European Journal of Chemistry are those of the specific author(s), and do not necessarily reflect the views of Atlanta Publishing House LLC, or European Journal of Chemistry, or any of its employees.

Copyright 2019 Atlanta Publishing House LLC. All rights reserved. This site is owned and operated by Atlanta Publishing House LLC whose registered office is 4614 Lavista road, Tucker, GA, 30084, USA. Registered in USA.

hatay escort hatay escort corlu escort corum escort burgaz escort giresun escort aydin escort ordu escort erzincan escort hatay escort sivas escort rize escort edirne escort aksaray escort kibris escort isparta escort erzurum escort tekirdag escort usak escort urfa escort kastamonu escort kibris escort manisa escort giresun escort urfa escort nevsehir escort sivas escort yalova escort ordu escort hatay escort yalova escort amasya escort kayseri escort ordu escort maras escort canakkale escort yalova escort balikesir escort manisa escort urfa escort mugla escort trabzon escort bolu escort corlu escort diyarbakir escort isparta escort kutahya escort elazig escort erzurum escort sakarya escort afyon escort kutahya escort konya escort agri escort cesme escort sinop escort sivas escort konya escort kibris escort adapazari escort luleburgaz escort adana escort kibris escort rize escort sakarya escort alanya escort isparta escort burdur escort konya escort bitlis escort canakkale escort sivas escort amasya escort mus escort aydin escort van escort yalova escort kastamonu escort mardin escort bolu escort afyon escort sakarya escort isparta escort tokat escort trakya escort bayburt escort urfa escort mardin escort