Enhancing the Antioxidant Characteristics of Phenolic Acids by Their Conversion into Cholinium Salts
authors Sintra, TE; Luis, A; Rocha, SN; Ferreira, AIMCL; Goncalves, F; Santos, LMNBF; Neves, BM; Freire, MG; Ventura, SPM; Coutinho, JAP
nationality International
journal ACS SUSTAINABLE CHEMISTRY & ENGINEERING
author keywords Antioxidant salts; Ecotoxicity; Cytotoxicity; Solubility; Anti-inflammatory activity
keywords CARBOXYLATE IONIC LIQUIDS; FISCHERI MARINE-BACTERIA; VIBRIO-FISCHERI; CAFFEIC ACID; OXIDATIVE STRESS; ELLAGIC ACID; IN-VITRO; TOXICITY; BIODEGRADATION; BIOMATERIALS
abstract Because of the close relation between oxidative stress and a plethora of inflammatory diseases, antioxidants have received an increased attention for incorporation into dermatological products. Their use and absorption are, however, limited by their low solubility in water-rich formulations. Herein, a set of novel cholinium-based salts, namely dicholinium ellagate and cholinium caffeate, syringate, vanillate, gallate, and salicylate, were synthesized and characterized. Their melting and decomposition temperatures, water solubility, and toxicological, antioxidant, cytotoxicity and pro-/anti-inflammatory activities were addressed. These new salts, exclusively composed of ions derived from natural sources, display a high thermal stability-up to 150 degrees C. The synthesized compounds are significantly more soluble in water (on average, 3 orders of magnitude higher) than the corresponding phenolic acids. Furthermore, they present not only similar but even higher antioxidant and anti-inflammatory activities, as well as comparable cytotoxicity and lower ecotoxicity profiles than their acidic precursors. Among all the investigated salts, dicholinium ellagate is the most promising synthesized salt when considering the respective antioxidant and anti-inflammatory activities. Because all the synthesized salts are based on the cholinium cation, they can further be envisaged as essential nutrients to be used in oral drugs.
publisher AMER CHEMICAL SOC
issn 2168-0485
year published 2015
volume 3
issue 10
beginning page 2558
ending page 2565
digital object identifier (doi) 10.1021/acssuschemeng.5b00751
web of science category Chemistry, Multidisciplinary; GREEN & SUSTAINABLE SCIENCE & TECHNOLOGY; Engineering, Chemical
subject category Chemistry; Science & Technology - Other Topics; Engineering
unique article identifier WOS:000362468600026
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journal analysis (jcr 2017):
journal impact factor 6.140
5 year journal impact factor 6.415
category normalized journal impact factor percentile 87.588
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