European Journal of Chemistry 2015, 6(4), 367-373. doi:10.5155/eurjchem.6.4.367-373.1298

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, Accepted: 08 Aug 2015, Published: 31 Dec 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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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. 19 Sep. 2019
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

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