Please use this identifier to cite or link to this item: http://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
RMID: 0020102769
DOI: 10.1021/jf1038162
Appears in Collections:Agriculture, Food and Wine publications

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