2024-03-28T20:41:01Z
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2015-12-31T11:02:45Z
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New route for synthesis of 3- and 5-caffeoylquinic acids via protected quinic acids
Kadidae, La Ode
Usami, Akira
Koyama, Tomoya
Honda, Mitsunori
Kunimoto, Ko-Ki
Hydrolysis
Esterification
Chemical synthesis
Caffeoylquinic acids
Protected quinic acids
Dimethoxy caffeoyl chloride
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.
Atlanta Publishing House LLC
2015-12-31
info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
application/pdf
https://www.eurjchem.com/index.php/eurjchem/article/view/1298
10.5155/eurjchem.6.4.367-373.1298
European Journal of Chemistry; Vol. 6 No. 4 (2015): December 2015; 367-373
2153-2257
2153-2249
eng
https://www.eurjchem.com/index.php/eurjchem/article/view/1298/pdf_1298