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Synthesis of Esters Via a Greener Steglich Esterification in Acetonitrile
Published on: October 30, 2018
Effect of saliva esterase activity on ester solutions and possible consequences for the in-mouth ester release during
María Pérez-Jiménez1, Nuria Rocha-Alcubilla1, María Ángeles Pozo-Bayón1
1Instituto de Investigación en Ciencias de la Alimentación (CIAL) CSIC-UAM, Madrid, Spain.
Abstract:
The aim of this study was to investigate the role of saliva esterase activity on carboxylic esters typically associated with pleasant and fruity aromas in wine. For this, ex vivo experiments using the same fresh and inactivated (without enzymatic activity) human saliva with a mixture of carboxylic esters with different aliphatic chain length (ethyl butanoate, ethyl pentanoate, ethyl hexanoate, ethyl octanoate, ethyl decanoate, and isoamyl acetate) were prepared. Liquid-liquid extraction with dichloromethane and GC-MS analysis were applied to the saliva systems in order to determine the reduction in ester content and the formation of their corresponding metabolic products (carboxylic acids) in the saliva systems before and after incubation at 37C. In addition, to check if there was a relationship between the susceptibility of esters to saliva hydrolysis and the amount of in-mouth ester release during wine intake, the remaining oral amount of each ester was determined by comparing the intraoral amount immediately after spitting out the wine and 4 min later. Ex vivo experiments showed ester degradation by saliva esterase enzymes mainly acted on long chain esters (ethyl octanoate and ethyl decanoate), which gave rise to the formation of their corresponding carboxylic acids. Nonetheless, in spite of their higher susceptibility to saliva enzymes, in vivo experiments showed that long chain carboxylic esters remained in the oral cavity long after swallowing. This confirmed that ester hydrophobicity is closely related to the in-mouth temporal release of these odorants and, therefore, behind wine aroma persistence. In wines, esters represent a group of aromatic compounds of great interest since they are linked to pleasant fruity aroma nuances. Today wine consumers are demanding fresh and long persistent fruity aromatic wines. The present research contributes to better understanding the relationship between ester content in the wine and oral aroma release experienced during wine tasting, considering the changes in these compounds during oral processing. This is a necessary step when trying to unravel the factors involved in wine aroma perception and in consumer preferences, and it represents a necessary knowledge in promoting winemaking practices (e.g., the use of selected microorganisms) for improving the type and amount of these aroma compounds in the wine.
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