EventsThe 18th International Electronic Conference on Synthetic Organic Chemistry
Published
This submission belongs to the session b. Bioorganic, Medicinal and Natural Products Chemistry of the event The 18th International Electronic Conference on Synthetic Organic Chemistry
Published date
03 Nov, 2014
Citation
Marcin Lukasiewicz, Piotr Jakubowski, Determination of Complexation Parameters for β-Cyclodextrin and Randomly Methylated β-Cyclodextrin Inclusion Complexes of p-Cumaric Acid Using Reversed-Phase Liquid Chromatography, in Proceedings of The 18th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2014, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-18-b028
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Determination of Complexation Parameters for β-Cyclodextrin and Randomly Methylated β-Cyclodextrin Inclusion Complexes of p-Cumaric Acid Using Reversed-Phase Liquid Chromatography

Piotr Jakubowski 1
1. Univeristy of Agriculture in Krakow, Faculty of Food Technology
Abstract
p-cumaric acid (PCA) i.e. hydroxycinnamic acid is a one of the major component of lignin. PCA can be found in a wide variety of edible plants including peanuts, beans, tomatoes, carrots, garlic etc. It is also found in wine and vinegar. PCA has strong antioxidant properties and is known to reduce the risk of stomach cancer by reducing the formation of carcinogenic nitrosamines. According to that tha main goal of presente dpaper is to establish the basic properties of PCA complexes with some cyclodextrin. Host-guest complexation with cyclodextrins may be interesting to increase the bioavailability of PCA in functional food product. During the research an on-line complexation of p-cumaric acid  with β-cyclodextrin (CD) and and Randomly Methylated β-cyclodextrin (RMCD) was performed using RP-HPLC system. Due to the complex formation of CD with a guest molecule - PCA a significant changes in retention times of PCA was observed. The investigation was performed as a function of temperature as well as cyclodextrin concentration in liquid phase. As a result apparent formation constant – KF of PCA/CD and PCA/RMCD were calculated. Based on KF some thermodynamic properties were obtained including standard enthalpy, standard entropy and free Gibbs energy of host-guest complexation. It was shown that the stoichiometry of the complex in both cases is 1:1 and the complexation is an exothermic process. From the other hand the positive value of Gibbs free energy clearly designate the process as forced one. The increase in temperature influence on Gibbs free energy by means of increase of this parameter. Additionally the differences between CD and RMCD as a hosting agents were shown.
Keywords
Cyclodextrin
complexation
HPLC
thermodynamics
apparent formation constant
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