OXI-002: Catalytic Lipophilization of Natural Antioxidants

Chlorogenic acid (CGA), a natural polyphenol widespread in nature (plants, vegetables, fruits), displays several pharmacological and biological activities such as antioxidative, antibacterial, antihypertensive, antitumor, anti-inflammatory. However, its highly hydrophilic structure strongly limits its bioavailability and hinders the use into oil-based products such as cosmetic and nutraceutical preparations. To overcome this drawback, CGA can be lipophilized through esterification with a fatty alcohol. The use of heterogeneous Brønsted solid acid catalysts, such as the sulphonic resins Amberlite® IR120 and Amberlyst® 15, resulted greatly effective in the direct acylation of CGA with several fatty alcohols (2 to 18 carbon atom) in a sustainable, solvent free, one-pot reaction (Scheme 1).

Ethyl, butyl, octyl- and lauryl- chlorogenates were isolated in high yields (up to 93%) and fully characterized by NMR and LC-MS analyses. The antioxidant activity of these products, estimated through the DPPH test, was found to be higher than unsubstituted CGA (Figure 1).

V. Pappalardo et al., Antioxidants 2023, 12, 218.

Euro Fed Lipid e.V.
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