A natural antioxidant, widely spread in plants, chlorogenic acid (CGA), can be lipophilized through a heterogeneous, non-enzymatic, catalytic process. Thus, sulfonic resins under no solvent conditions allow to obtain a series of esters in up to 93% yield through reaction of CGA with fatty alcohols of different chain length. The reaction takes place in one single step under mild conditions with conversions up to 96% and selectivity up to 99%. Product recovery in high purity was very easy and the esters obtained were fully characterized with spectroscopic techniques and through the DPPH test to verify the preservation of antioxidant activity. According to this test, all of them showed increased activity with respect to the parent acid and anyway higher than butylated hydroxyanisole. An in-silico method also suggested their very low toxicity. The increased lipophilicity of the esters allows their formulation in cosmetic and nutraceutic lipid-based products.

A Green Lipophilization Reaction of a Natural Antioxidant / V. Pappalardo, N. Ravasio, E. Falletta, M. Cristina De Rosa, F. Zaccheria. - In: ANTIOXIDANTS. - ISSN 2076-3921. - 12:2(2023 Jan 18), pp. 218.1-218.11. [10.3390/antiox12020218]

A Green Lipophilization Reaction of a Natural Antioxidant

E. Falletta;
2023

Abstract

A natural antioxidant, widely spread in plants, chlorogenic acid (CGA), can be lipophilized through a heterogeneous, non-enzymatic, catalytic process. Thus, sulfonic resins under no solvent conditions allow to obtain a series of esters in up to 93% yield through reaction of CGA with fatty alcohols of different chain length. The reaction takes place in one single step under mild conditions with conversions up to 96% and selectivity up to 99%. Product recovery in high purity was very easy and the esters obtained were fully characterized with spectroscopic techniques and through the DPPH test to verify the preservation of antioxidant activity. According to this test, all of them showed increased activity with respect to the parent acid and anyway higher than butylated hydroxyanisole. An in-silico method also suggested their very low toxicity. The increased lipophilicity of the esters allows their formulation in cosmetic and nutraceutic lipid-based products.
natural antioxidants; lipophilization; food waste valorization; sustainable chemistry
Settore CHIM/04 - Chimica Industriale
Article (author)
File in questo prodotto:
File Dimensione Formato  
antioxidants-12-00218.pdf

accesso aperto

Tipologia: Publisher's version/PDF
Dimensione 1.16 MB
Formato Adobe PDF
1.16 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/951391
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus ND
  • ???jsp.display-item.citation.isi??? ND
social impact