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Side chain influencing the interaction between β ‐cyclodextrin and vanillin
Author(s) -
Zeng Zhangfu,
Fang Yanxiong,
Ji Hongbing
Publication year - 2012
Publication title -
flavour and fragrance journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.393
H-Index - 70
eISSN - 1099-1026
pISSN - 0882-5734
DOI - 10.1002/ffj.3115
Subject(s) - chemistry , vanillin , cyclodextrin , hydrogen bond , intermolecular force , hydrophobic effect , covalent bond , aldehyde , molecule , stereochemistry , computational chemistry , organic chemistry , catalysis
The reason for low encapsulation efficiency of vanillin compared to p ‐hydroxybenzaldehyde within β ‐cyclodextrin was investigated. Fourier transform infrared spectra proved intermolecular interaction between guest and β ‐cyclodextrin. UV–visible studies indicated that vanillin and p ‐hydroxybenzaldehyde form 1:1 inclusion complexes with β ‐cyclodextrin. Nuclear magnetic resonance and quantum computational methods gave the most favourable orientation in which the guest molecule (vanillin or p ‐hydroxybenzaldehyde) is totally sequestered in the hydrophobic cavity of the cyclodextrin with the phenolic end located near the primary hydroxyls of the β ‐cyclodextrin and the aldehyde group near the secondary hydroxyls with hydrogen bonding formation. Encapsulation efficiency of the β ‐cyclodextrin inclusion with vanillin is about 29% lower than that with p ‐hydroxybenzaldehyde. This result could be attributable to the effect that the side chain methoxy group weakened the guest/host non‐covalent intermolecular interaction, specifically, hydrogen bond interaction. Copyright © 2012 John Wiley & Sons, Ltd.