Structural determination of vanillin, isovanillin and ethylvanillin by means of gas electron diffraction and theoretical calculations

Abstract

The molecular structures of vanillin (4-hydroxy-3-methoxybenzaldehyde), isovanillin (3-hydroxy-4-methoxybenzaldehyde) and ethylvanillin (3-ethoxy-4-hydroxybenzaldehyde) were determined by means of gas electron diffraction.

Chemical Simulation and Quantum Chemical Calculation of Lignin Model Compounds

“…Then they estimated that the hydrogen bond energy was 18.06 to 18.51 KJ/mol. Egawa et al (2006) confirmed the molecular structure of isovanillin and ethyl vanillin by the gas electron diffraction method and theoretical calculations. Jakobsons et al (1981) used an atoms-potential energy function (AAPE) and CNDO/2 method to analyze the conformations of model compounds including vanillin, o-hydroxyl benzaldehyde, and their intramolecular hydrogen bonding, rotational potential energy, and relative stability in theory.…”

Nature’s Chemical Signatures in Human Olfaction: A Foodborne Perspective for Future Biotechnology

“…[4] In the late 1980s, a team led by Ryō ji Noyori, who won the 2001 Nobel Prize for Chemistry in recognition of his work on this process by using BINAP ruthenium catalysts, was the first to develop the myrcenebased synthesis of (À)-menthol, today known as the "Takasago process", involving the asymmetric isomerization of diethylgeranylamine to 3-(R)-citronellal enamine using the catalyst [{(S)-BINAP} 2 Ru]ClO 4 as a novel key reaction step. [7] The biocatalytic production of flavor naturals that determine chemosensory percepts of foods and beverages is an ever challenging target for academic and industrial research. [6] Moreover, organic chemistry was successful to produce non-natural homologues of even higher impact, for example, the nowadays widely used ethylvanillin showing a circa four-fold enhanced flavor intensity when compared to its natural analogue vanillin.…”

“…[6] Moreover, organic chemistry was successful to produce non-natural homologues of even higher impact, for example, the nowadays widely used ethylvanillin showing a circa four-fold enhanced flavor intensity when compared to its natural analogue vanillin. [7] The biocatalytic production of flavor naturals that determine chemosensory percepts of foods and beverages is an ever challenging target for academic and industrial research. Advances in chemical trace analysis and post-genomic progress at the chemistry-biology interface revealed odor qualities of natures chemosensory entities to be defined by odorant-induced olfactory receptor activity patterns.…”

Molecular structure of trans-cinnamaldehyde as determined by gas electron diffraction aided by DFT calculations

“…In spite of the physiological importance of trans-cinnamaldehyde, its geometrical structure has not been thoroughly studied. As in the case of vanillin and isovanillin [3], trans-cinnamaldehyde is expected to have two conformers, s-cis and s-trans, which are different from each other in the orientation of the aldehyde group (see Fig. 1).…”

“…Recently we have succeeded in the structural determination of some compounds with characteristic odors such as menthol [1], isomenthol [1], carvone [2], vanillin [3], isovanillin [3] and ethylvanillin [3], by means of gas electron diffraction (GED). In the present study, trans-cinnamaldehyde ((E)-3-phenyl-2-propenal) has been chosen as the target.…”