Terpinen-4-ol–B12N12 and Linalool–B12N12 Compounds as a Natural Replacement of Nitrites and Nitrates in Meat Products: a DFT, QTAIM, and Molecular Docking Study

Abstract

Nitrites and nitrates are commonly used in meat products to extend shelf life, stabilize color, and inhibit microbial growth. However, they can react with amines and amides, forming carcinogenic compounds. Essential oils are being considered as a natural replacement, but their use in the food industry is limited due to instability, volatility, and water insolubility factors. One solution is to encapsulate or interact the oils with other molecules. In this research, we examined the effective role of B₁₂N₁₂ in interacting with terpinen-4-ol and linalool oils as a stabilizer and nanocarrier for their potential application in the food industry, utilizing density functional calculations (DFT) in both gas and water phases. The adsorption energy values and thermodynamic parameters indicated that the oils adsorb onto the B₁₂N₁₂ cage through a chemisorption process. This process is exothermic and involves the formation of a partial covalent bond (B–O) between the cage and the oils. These findings suggest that the B₁₂N₁₂ cage effectively stabilizes and carries the oils. The vibrational frequency and quantum molecular descriptors (QMDs) calculations suggested that the terpinen-4-ol–B₁₂N₁₂ and linalool–B₁₂N₁₂ complexes are stable. Additionally, the solvation energy values, along with notable alterations in the polarity of the complexes, indicated the potential of the B₁₂N₁₂ cage as an effective solubilizer for the oils in water. The analysis using atoms in molecules (AIM) indicated that the interaction between the oils and the cage involves a partial covalent bond. Additionally, molecular electrostatic potential (MEP), Mulliken population analysis (MPA), and UV-Vis spectra for the compounds were computed. The antimicrobial effectiveness of terpinen-4-ol, linalool, terpinen-4-ol–B₁₂N₁₂, and linalool–B₁₂N₁₂ compounds against Escherichia coli (PDB ID: 4WUB) and v (PDB ID: 3VSL) bacteria was investigated using molecular docking techniques. The calculations indicated that terpinen-4-ol and linalool oils demonstrate higher binding affinities in comparison to terpinen-4-ol–B₁₂N₁₂ and linalool–B₁₂N₁₂ compounds when interacting with the 4WUB and 3VSL receptors. The results suggest that terpinen-4-ol and linalool oils, when combined with B₁₂N₁₂, have the potential to serve as natural substitutes for nitrites and nitrates in meat products.