Molecular Properties of Astaxanthin in Water/Ethanol Solutions from Computer Simulations

J Phys Chem B. 2016 Sep 8;120(35):9322-8. doi: 10.1021/acs.jpcb.6b06055. Epub 2016 Aug 26.

Abstract

Astaxanthin (AXT) is a reference model of xanthophyll carotenoids, which is used in medicine and food industry, and has potential applications in nanotechnology. Because of its importance, there is a great interest in understanding its molecular properties and aggregation mechanism in water and mixed solvents. In this paper, we report a novel model of AXT for molecular dynamics simulation. The model is used to estimate different properties of the molecule in pure solutions and in water/ethanol mixtures. The calculated diffusion coefficients of AXT in pure water and ethanol are (3.22 ± 0.01) × 10(-6) cm(2) s(-1) and (2.7 ± 0.4) × 10(-6) cm(2) s(-1), respectively. Our simulations also show that the content of water plays a clear effect on the morphology of the AXT aggregation in water/ethanol mixture. In up to 75% (v/v) water concentration, a loosely connected network of dimers and trimers and two-dimensional array structures are observed. At higher water concentrations, AXT molecules form more compact three-dimensional structures that are preferentially solvated by the ethanol molecules. The ethanol preferential binding and the formation of a well connected hydrogen bonding network on these AXT clusters, suggest that such preferential solvation can play an important role in controlling the aggregate structure.

MeSH terms

  • Computer Simulation*
  • Ethanol / chemistry*
  • Hydrogen Bonding
  • Molecular Dynamics Simulation*
  • Molecular Structure
  • Solutions
  • Water / chemistry*
  • Xanthophylls / chemistry

Substances

  • Solutions
  • Xanthophylls
  • Water
  • Ethanol
  • astaxanthine