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https://hdl.handle.net/2440/69197
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Type: | Journal article |
Title: | The formation of wine lactone from grape-derived secondary metabolites |
Author: | Giaccio, J. Capone, D. Hakansson, A. Smyth, H. Elsey, G. Sefton, M. Taylor, D. |
Citation: | Journal of Agricultural and Food Chemistry, 2011; 59(2):660-664 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2011 |
ISSN: | 0021-8561 1520-5118 |
Statement of Responsibility: | Joanne Giaccio, Dimitra L. Capone, Anders E. Håkansson, Heather E. Smyth, Gordon M. Elsey, Mark A. Sefton, and Dennis K. Taylor |
Abstract: | Wine lactone (i.e., 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one, 1a/1b) was formed hydrolytically at wine pH from both racemic (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (3) and the corresponding glucose ester 2a at 45 °C but at room temperature was only formed from the acid 3. The glucose ester does not appear to be a significant precursor for the formation of wine lactone in wine. The slow formation of wine lactone from the free acid 3 indicates that the acid is not likely to be an important precursor to wine lactone in young wines unless present in high concentration (≫ 1 mg/L), but could be a significant precursor to wine lactone in wine that is several years old. The wine lactone formed in hydrolysates of the (6R)-enantiomer of 3 was partially enriched in the (3S,3aS,7aR)-enantiomer 1a when the hydrolysis was conducted at pH 3.2 and 100 °C in a closed vessel or under simultaneous distillation-extraction (SDE) conditions, and the enantiomeric excess (ee) varied from 5 to 22%. Hydrolysis of (6R)-3 in sealed ampules at 45 °C and at pH 3.0, 3.2, or 3.4 gave near-racemic wine lactone, but when the hydrolyses were conducted at room temperature, the product was enriched in the (3S,3aS,7aR)-enantiomer 1a and the ee was greater at higher pH (up to 60% at pH 3.4). |
Keywords: | Wine lactone wine precursor hydrolysis chiral analysis aroma flavor |
Rights: | Copyright © 2010 American Chemical Society |
DOI: | 10.1021/jf1038162 |
Published version: | http://dx.doi.org/10.1021/jf1038162 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest |
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