TAILIEUCHUNG - A Challenging Classic Coupling: Esterification of Camphoric Acid - a Steric-Hindered Polar Carboxylic Acid and Solanesol - a Long-Chain Nonpolar Alcohol
We have developed two esterification strategies for a challenging coupling between camphoric acid and solanesol to achieve a hybrid natural product - solanesyl camphorate. Both synthetic strategies applied the classic activation mode of carboxylic acid group by anhydride formation to overcome the difficulties caused by steric hindrance and the difference in polarity of two reactants. | VNU Journal of Science: Natural Sciences and Technology, Vol. 32, No. 4 (2016) 220-227 A Challenging Classic Coupling: Esterification of Camphoric Acid - a Steric-Hindered Polar Carboxylic Acid and Solanesol - a Long-Chain Nonpolar Alcohol Phung Nhu Hoa1, Nguyen Thi Thu Trang1,2, Nguyen Tien Tuan Anh1, Pham Van Phong1, Nguyen Van Ky1,* 1 2 Department of Chemistry, VNU University of Science National Institute of Medicinal Materials, Ministry of Health, Hanoi, Vietnam Received 01 August 2016 Revised 30 August 2016; Accepted 01 September 2016 Abstract: We have developed two esterification strategies for a challenging coupling between camphoric acid and solanesol to achieve a hybrid natural product - solanesyl camphorate. Both synthetic strategies applied the classic activation mode of carboxylic acid group by anhydride formation to overcome the difficulties caused by steric hindrance and the difference in polarity of two reactants. The first method took advantages of easy prepared camphoric anhydride from camphoric acid, whereas the second one allowed direct esterification via in situ anhydride formation. Moreover, no solvent is required in synthetic process. This work would provide greener approaches for syntheses of hybrid esters from similar natural products. Keywords: Solanesyl Camphorate, antiseptic, wound healing , challenging coupling, solvent-free. 1. Introduction camphorate ester (Figure 1) [7], the new hybrid product between camphoric acid and solanesol, would possess both antimicrobial and wound healing activities to synergistically enhance body tissue repairs after injuries. Unfortunately, there has been no report on the synthesis of this ester. Hence, in this research, we described the first synthesis of solanesyl camphorate as a potential biologically active candidate. Along with multiple organ failure, infection accounts for 80% of late deaths in hospital after trauma [1]. ∗Therefore, it is ideal to have a way to simultaneously kill or prevent .
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