Essential features for antioxidant capacity of ascorbic acid (vitamin C)

J Mol Model. 2021 Dec 3;28(1):1. doi: 10.1007/s00894-021-04994-9.


Vitamin C or ascorbic acid is an indispensable micronutrient for human health found principally on citrus species such as lemon and orange fruits and vegetables. It was involved in the production of proteins such as collagen. Its biochemical mechanism is related to its antioxidant capacity; however, its function at the cellular level is still unclear. Several theoretical studies about antioxidant and redox mechanisms for ascorbic acid were suggested; however, no derivative was proposed. Thereby, an electronic study of antioxidant capacity for ascorbic acid derivatives was performed using theoretical chemistry at the DFT/ B3LYP/6-311 + + (2d,2p) level of theory. Simplified derivatives show that enol hydroxyls are more important than any other functional group. The vicinal enolic hydroxyl on β position is more important for antioxidant capacity of ascorbic than hydroxyl on α position. According to our molecular modifications, the keto-alkene compound showed the best values when compared to ascorbic acid in some molecular characteristics. No lactone derivatives have superior application potential as antioxidant when compared with ascorbic acid. Several structures are possible to be proposed and were related to spin density contributions and the increase of chemical stability. New promising structural derivatives related to ascorbic acid can be developed in the future.

Keywords: Antioxidant mechanism; Ascorbic acid; DFT; Pharmacophore; Redox capacity.

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / metabolism
  • Antioxidants / pharmacology*
  • Ascorbic Acid / chemistry*
  • Ascorbic Acid / metabolism
  • Ascorbic Acid / pharmacology*
  • Humans
  • Lactones / chemistry
  • Lactones / metabolism
  • Metabolic Networks and Pathways
  • Molecular Structure
  • Oxidation-Reduction


  • Antioxidants
  • Lactones
  • Ascorbic Acid