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https://hdl.handle.net/2440/47267
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Type: | Journal article |
Title: | Rates of formation of cis- and trans-oak lactone from 3-methyl-4- hydroxyoctanoic acid |
Author: | Wilkinson, K. Elsey, G. Prager, R. Pollnitz, A. Sefton, M. |
Citation: | Journal of Agricultural and Food Chemistry, 2004; 52(13):4213-4218 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2004 |
ISSN: | 0021-8561 1520-5118 |
Abstract: | The rates of formation of both cis- and trans-oak lactone from the corresponding isomers of 3-methyl-4-hydroxyoctanoic acid have been measured in model wine at room temperature for a range of pH values. The half-life for formation of the trans-isomer at pH 2.9 was calculated to be 3.1 h, whereas that for the cis-isomer, at the same pH, was calculated to be 40.5 h. The ktrans/kcis ratio in model wine was found to 12.86 ± 1.34 over the range of pH values employed. A reason for the more facile formation of the trans-isomer, based on conformational reasons, has been proposed. In acidic aqueous media the equilibrium between the oak lactones and their corresponding ring-opened analogues was found to favor the former entirely, with no evidence for the latter being found. Implications of the present study for the future analysis of oak samples, as well as for the interpretation of existing data, are discussed. |
Keywords: | Oak wine oak lactone whiskey lactone kinetics lactonization |
DOI: | 10.1021/jf0496550 |
Published version: | http://dx.doi.org/10.1021/jf0496550 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest |
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